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Explore 418 cruise vacations

Showing Loading cruise vacations: All Destinations, September 2025 - November 2027
ENDS TONIGHT:
Select Caribbean sailings from $109 pp/pn
Showing 418 cruise vacations that match your search
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Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,190$1,622
per Cabin
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5 nights
Valiant Lady, Scarlet Lady, Resilient Lady & Brilliant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$1,190$1,622
per Cabin
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Departing on:
2025Best Rate
Fri, Sep 12 - Wed, Sep 17
from (US$)$1,190
2025
Fri, Sep 26 - Wed, Oct 01
from (US$)$2,700
2025
Fri, Nov 07 - Wed, Nov 12
from (US$)$1,790

Portsmouth to Lisbon, Casablanca & Spain

  • Portsmouth
  • La Coruña, Spain
  • Lisbon, Portugal
  • Casablanca, Morocco
  • Málaga, Spain
  • Ibiza, Spain
  • Barcelona
Sea Terrace cabins from
$6,890$10,330
per Cabin
13 nights
Scarlet Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea Terrace cabins from
$6,890$10,330
per Cabin
Departing on:
2025
Fri, Sep 12 - Thu, Sep 25
from (US$)$6,890
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70% off a 2nd Sailor + up to $500 off
Savings on new Brilliant Lady voyages, Europe, Caribbean and more through 2027.
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Greek Island Glow

  • Athens (Piraeus)
  • Santorini, Greece
  • Rhodes, Greece
  • Bodrum, Turkey
  • Mykonos, Greece
  • Athens (Piraeus)
Insider cabins from
$2,926$4,132
per Cabin
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7 nights
Resilient Lady & Scarlet Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,926$4,132
per Cabin
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Departing on:
2027Best Rate
Sun, Aug 01 - Sun, Aug 08
from (US$)$2,926
2025
Sun, Sep 14 - Sun, Sep 21
from (US$)$3,346
2025
Sun, Oct 12 - Sun, Oct 19
from (US$)$3,488

Fall Colors: Coastal Northeast & Canada

  • New York City, New York
  • Boston, Massachusetts
  • Eastport, Maine
  • Saint John, New Brunswick
  • Halifax, Nova Scotia
  • New York City, New York
Insider cabins from
$2,544$3,616
per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,544$3,616
per Cabin
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Departing on:
2025
Mon, Sep 15 - Tue, Sep 23
from (US$)$2,544Brilliant Lady's Inaugural Season

Istanbul, Santorini & More

  • Athens (Piraeus)
  • Istanbul, Turkey
  • Ephesus (Kuşadasi), Turkey
  • Mykonos, Greece
  • Rhodes, Greece
  • Santorini, Greece
  • Chania (Souda Bay), Crete, Greece
  • Athens (Piraeus)
Sea View cabins from
$5,500$8,034
per Cabin
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11 nights
Resilient Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$5,500$8,034
per Cabin
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Departing on:
2025
Sun, Sep 21 - Thu, Oct 02
from (US$)$5,500
★
EXTRA SAVINGS

Riviera Maya

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,090
per Cabin
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5 nights
Valiant Lady, Scarlet Lady & Resilient Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off a second Sailor
Insider cabins from
$1,090
per Cabin
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Departing on:
2025Best Rate
Sun, Nov 16 - Fri, Nov 21
from (US$)$1,090
2025
Sun, Sep 21 - Fri, Sep 26
from (US$)$1,190
2025
Sun, Dec 14 - Fri, Dec 19
from (US$)$1,090

Autumn Leaves: New York to Quebec

  • New York City, New York
  • Boston, Massachusetts
  • Eastport, Maine
  • Saint John, New Brunswick
  • Halifax, Nova Scotia
  • Québec City, Québec
Sea View cabins from
$2,580$3,658
per Cabin
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10 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$2,580$3,658
per Cabin
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Departing on:
2025
Tue, Sep 23 - Fri, Oct 03
from (US$)$2,580Brilliant Lady's Inaugural Season

Starry Nights in Greece & Croatia

  • Athens (Piraeus)
  • Santorini, Greece
  • Bodrum, Turkey
  • Mykonos, Greece
  • Dubrovnik, Croatia
  • Kotor, Montenegro
  • Corfu, Greece
  • Athens (Piraeus)
Sea View cabins from
$4,300$6,242
per Cabin
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10 nights
Resilient Lady & Scarlet Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$4,300$6,242
per Cabin
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Departing on:
2025Best Rate
Thu, Oct 02 - Sun, Oct 12
from (US$)$4,300
2026
Sun, Jun 14 - Wed, Jun 24
from (US$)$5,500
2026
Thu, Sep 10 - Sun, Sep 20
from (US$)$5,900

Mayan Sol

  • Miami, Florida
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,290$1,714
per Cabin
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5 nights
Valiant Lady, Resilient Lady & Scarlet Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off a second Sailor
Insider cabins from
$1,290$1,714
per Cabin
Loading
Departing on:
2025Best Rate
Sun, Oct 05 - Fri, Oct 10
from (US$)$1,290
2026
Mon, Jun 22 - Sat, Jun 27
from (US$)$1,890
2026
Sat, Nov 28 - Thu, Dec 03
from (US$)$1,590

Italy to France & Spain

  • Rome (Civitavecchia)
  • Cagliari, Sardinia, Italy
  • Tuscany/Cinque Terre (Marina di Carrara), Italy
  • Ajaccio, Corsica, France
  • Cannes, France
  • Valencia, Spain
  • Barcelona
Sea View cabins from
$3,582$5,312
per Cabin
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9 nights
Scarlet Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$3,582$5,312
per Cabin
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Departing on:
2025
Tue, Oct 07 - Thu, Oct 16
from (US$)$3,582

True Crime Voyage

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$1,490$2,082
per Cabin
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5 nights
Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$1,490$2,082
per Cabin
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Departing on:
2025
Fri, Oct 10 - Wed, Oct 15
from (US$)$1,490

Scarlet's Haunted Halloween Soirée

  • Barcelona
  • Palma de Mallorca, Spain
  • Casablanca, Morocco
  • Funchal, Madeira, Portugal
  • Santa Cruz de Tenerife, Spain
  • Miami, Florida
RockStar Quarters suites from
$10,800
per Cabin
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15 nights
Scarlet Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
RockStar Quarters suites from
$10,800
per Cabin
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Departing on:
2025
Thu, Oct 16 - Fri, Oct 31
from (US$)$10,800
Only suites remaining

Brilliant Lady Miami MerMaiden

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$2,704$3,928
per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off a second Sailor
Sea View cabins from
$2,704$3,928
per Cabin
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Departing on:
2025
Fri, Oct 17 - Sat, Oct 25
from (US$)$2,704Brilliant Lady's Inaugural Season

Mykonos Moons to Spanish Sunrises

  • Athens (Piraeus)
  • Mykonos, Greece
  • Catania, Sicily, Italy
  • Palma de Mallorca, Spain
  • Valencia, Spain
  • Barcelona
Sea Terrace cabins from
$3,920$5,766
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off a second Sailor
Sea Terrace cabins from
$3,920$5,766
per Cabin
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Departing on:
2025
Sun, Oct 19 - Sun, Oct 26
from (US$)$3,920

Riviera Maya: Halloween Edition

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,290$1,704
per Cabin
Loading
5 nights
Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off a second Sailor
Insider cabins from
$1,290$1,704
per Cabin
Loading
Departing on:
2025Best Rate
Sun, Oct 19 - Fri, Oct 24
from (US$)$1,290
2027
Sat, Oct 30 - Thu, Nov 04
from (US$)$1,590

Dominican Daze: Halloween Edition

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$1,692$2,388
per Cabin
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5 nights
Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off a second Sailor
Sea View cabins from
$1,692$2,388
per Cabin
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Departing on:
2025
Fri, Oct 24 - Wed, Oct 29
from (US$)$1,692

Resilient's Haunted Halloween Soirée

  • Barcelona
  • Valencia, Spain
  • Casablanca, Morocco
  • Las Palmas de Gran Canaria, Spain
  • Miami, Florida
RockStar Quarters suites from
$11,452
per Cabin
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14 nights
Resilient Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off a second Sailor
RockStar Quarters suites from
$11,452
per Cabin
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Departing on:
2025
Sun, Oct 26 - Sun, Nov 09
from (US$)$11,452
Only suites remaining

Valiant's Haunted Halloween Soirée

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$1,592$2,226
per Cabin
Loading
4 nights
Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off a second Sailor
Sea View cabins from
$1,592$2,226
per Cabin
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Departing on:
2025
Wed, Oct 29 - Sun, Nov 02
from (US$)$1,592
★
EXTRA SAVINGS

Scarlet's Haunted Halloween Soirée

  • Miami, Florida
  • Roatán, Honduras
  • Costa Maya, Mexico
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$1,654
per Cabin
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7 nights
Scarlet Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off a second Sailor
Sea View cabins from
$1,654
per Cabin
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Departing on:
2025
Fri, Oct 31 - Fri, Nov 07
from (US$)$1,654

Western Caribbean: From Miami to Bimini

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,806$2,526
per Cabin
Loading
7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off a second Sailor
Insider cabins from
$1,806$2,526
per Cabin
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Departing on:
2025
Sat, Nov 01 - Sat, Nov 08
from (US$)$1,806Brilliant Lady's Inaugural Season
★
EXTRA SAVINGS

One-way to SJ: DR, St. Maarten & BVI

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • San Juan, Puerto Rico
Insider cabins from
$1,304
per Cabin
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6 nights
Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$1,304
per Cabin
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Departing on:
2025
Sun, Nov 02 - Sat, Nov 08
from (US$)$1,304

Colorful Curaçao to the Charming Caymans

  • Miami, Florida
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
$2,856$4,128
per Cabin
Loading
12 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off a second Sailor
Insider cabins from
$2,856$4,128
per Cabin
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Departing on:
2025
Sat, Nov 08 - Thu, Nov 20
from (US$)$2,856Brilliant Lady's Inaugural Season

Saint (Isles) & Seas of the Caribbean

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Bridgetown, Barbados
  • Castries, St. Lucia
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
$2,226$3,166
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off a second Sailor
Insider cabins from
$2,226$3,166
per Cabin
Loading
Departing on:
2027Best Rate
Sat, Jan 02 - Sat, Jan 09
from (US$)$2,226
2025
Sat, Nov 08 - Sat, Nov 15
from (US$)$3,068
2026
Sat, Mar 21 - Sat, Mar 28
from (US$)$3,360
★
EXTRA SAVINGS

Western Caribbean Charm

  • Miami, Florida
  • Costa Maya, Mexico
  • Roatán, Honduras
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$2,640$3,754
per Cabin
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6 nights
Resilient Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$2,640$3,754
per Cabin
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Departing on:
2025
Sun, Nov 09 - Sat, Nov 15
from (US$)$2,640

Fire & Sunset Soirées

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,112$1,448
per Cabin
Loading
4 nights
Scarlet Lady, Resilient Lady, Brilliant Lady & Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off a second Sailor
Insider cabins from
$1,112$1,448
per Cabin
Loading
Departing on:
2027Best Rate
Thu, Sep 09 - Mon, Sep 13
from (US$)$1,112
2025
Wed, Nov 12 - Sun, Nov 16
from (US$)$1,592
2025
Wed, Nov 26 - Sun, Nov 30
from (US$)$1,592
* Port changes in place on select sailings — see full cruise details
★
EXTRA SAVINGS

San Juan Sunrises & Dominican Dreams

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,516
per Cabin
Loading
7 nights
Resilient Lady & Scarlet Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off a second Sailor
Insider cabins from
$1,516
per Cabin
Loading
Departing on:
2025Best Rate
Sat, Nov 15 - Sat, Nov 22
from (US$)$1,516
2026
Sat, Mar 28 - Sat, Apr 04
from (US$)$2,520
2026
Sat, Apr 18 - Sat, Apr 25
from (US$)$2,506
★
EXTRA SAVINGS

Sunny Miles of Tropical Isles

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Bridgetown, Barbados
  • Castries, St. Lucia
  • Fort-de-France, Martinique
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
Insider cabins from
$1,522
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off a second Sailor
Insider cabins from
$1,522
per Cabin
Loading
Departing on:
2025Best Rate
Sat, Nov 15 - Sat, Nov 22
from (US$)$1,522
2026
Sat, Feb 28 - Sat, Mar 07
from (US$)$3,080
2026
Sat, Nov 07 - Sat, Nov 14
from (US$)$2,366
★
EXTRA SAVINGS

Sunny San Juan & Isles of Beach Miles

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • St. Croix, U.S. Virgin Islands
  • Miami, Florida
Insider cabins from
$1,736
per Cabin
Loading
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$1,736
per Cabin
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Departing on:
2025
Thu, Nov 20 - Fri, Nov 28
from (US$)$1,736Brilliant Lady's Inaugural Season

Miami, Grand Turk (& back)

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,440$1,950
per Cabin
Loading
5 nights
Scarlet Lady, Resilient Lady & Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off a second Sailor
Insider cabins from
$1,440$1,950
per Cabin
Loading
Departing on:
2027Best Rate
Sat, Oct 16 - Thu, Oct 21
from (US$)$1,440
2025
Fri, Nov 21 - Wed, Nov 26
from (US$)$2,190
2025
Sun, Nov 30 - Fri, Dec 05
from (US$)$2,090

Cayman Coves & Jamaican Waterfalls

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$1,806$2,526
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off a second Sailor
Sea View cabins from
$1,806$2,526
per Cabin
Loading
Departing on:
2025Best Rate
Sat, Nov 22 - Sat, Nov 29
from (US$)$1,806
2025
Sat, Dec 06 - Sat, Dec 13
from (US$)$1,806
2026
Sat, Jan 24 - Sat, Jan 31
from (US$)$2,226
★
EXTRA SAVINGS

Thanksgiving in the Lesser Antilles

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Basseterre, St. Kitts and Nevis
  • St. John's, Antigua
  • Castries, St. Lucia
  • Charlotte Amalie, St. Thomas
  • San Juan, Puerto Rico
Insider cabins from
$1,518
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off a second Sailor
Insider cabins from
$1,518
per Cabin
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Departing on:
2025
Sat, Nov 22 - Sat, Nov 29
from (US$)$1,518

Antigua Waves & Grand Turk Caves

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • St. John's, Antigua
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
  • Miami, Florida
Insider cabins from
$2,142$3,076
per Cabin
Loading
9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off a second Sailor
Insider cabins from
$2,142$3,076
per Cabin
Loading
Departing on:
2025Best Rate
Fri, Nov 28 - Sun, Dec 07
from (US$)$2,142Brilliant Lady's Inaugural Season
2026
Fri, Feb 20 - Sun, Mar 01
from (US$)$3,942Brilliant Lady's Inaugural Season
★
EXTRA SAVINGS

San Juan to Barbados & the St. Isles

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • Roseau, Dominica
  • Bridgetown, Barbados
  • San Juan, Puerto Rico
Insider cabins from
$1,298
per Cabin
Loading
6 nights
Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off a second Sailor
Insider cabins from
$1,298
per Cabin
Loading
Departing on:
2025
Sat, Nov 29 - Fri, Dec 05
from (US$)$1,298
★
EXTRA SAVINGS

San Juan, Samaná & Bimini

  • Miami, Florida
  • San Juan, Puerto Rico
  • Samaná, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,522
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off a second Sailor
Insider cabins from
$1,522
per Cabin
Loading
Departing on:
2025Best Rate
Sat, Nov 29 - Sat, Dec 06
from (US$)$1,522
2026
Sat, Jan 17 - Sat, Jan 24
from (US$)$2,226
★
EXTRA SAVINGS

Nicky Jam x Virgin Voyages

  • San Juan, Puerto Rico
  • Willemstad, Curaçao
  • Oranjestad, Aruba
  • Roseau, Dominica
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
$1,740
per Cabin
Loading
8 nights
Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$1,740
per Cabin
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Departing on:
2025
Fri, Dec 05 - Sat, Dec 13
from (US$)$1,740

Aruban Sunsets & Calm Cayman Days

  • Miami, Florida
  • Oranjestad, Aruba
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
$2,618$3,784
per Cabin
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11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,618$3,784
per Cabin
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Departing on:
2025Best Rate
Sun, Dec 07 - Thu, Dec 18
from (US$)$2,618Brilliant Lady's Inaugural Season
2026
Sun, Mar 01 - Thu, Mar 12
from (US$)$3,278Brilliant Lady's Inaugural Season

Cayman Coves & Jamaican Waterfalls

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$1,806$2,526
per Cabin
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7 nights
Resilient Lady
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+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$1,806$2,526
per Cabin
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Departing on:
2025Best Rate
Sat, Dec 13 - Sat, Dec 20
from (US$)$1,806
2026
Sat, Feb 07 - Sat, Feb 14
from (US$)$2,366
★
EXTRA SAVINGS

St. Lucia, St. Maarten, Barbados & More

  • San Juan, Puerto Rico
  • Basseterre, St. Kitts and Nevis
  • Castries, St. Lucia
  • Roseau, Dominica
  • Bridgetown, Barbados
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
$1,518
per Cabin
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7 nights
Valiant Lady
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+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$1,518
per Cabin
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Departing on:
2025
Sat, Dec 13 - Sat, Dec 20
from (US$)$1,518
★
EXTRA SAVINGS

Brilliant Caribbean Holidays

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Samaná, Dominican Republic
  • Miami, Florida
Sea View cabins from
$1,890
per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$1,890
per Cabin
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Departing on:
2025
Thu, Dec 18 - Fri, Dec 26
from (US$)$1,890Brilliant Lady's Inaugural Season

Resilient Caribbean Holidays

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$2,506$3,612
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$2,506$3,612
per Cabin
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Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from (US$)$2,506

Valiant Caribbean Holidays

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • St. John's, Antigua
  • Castries, St. Lucia
  • Tortola, British Virgin Islands
  • San Juan, Puerto Rico
Sea View cabins from
$2,508$3,698
per Cabin
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7 nights
Valiant Lady
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+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$2,508$3,698
per Cabin
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Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from (US$)$2,508

Scarlet Caribbean Holidays

  • Miami, Florida
  • Nassau, Bahamas
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$1,592$2,242
per Cabin
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4 nights
Scarlet Lady
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+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$1,592$2,242
per Cabin
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Departing on:
2025Best Rate
Wed, Dec 24 - Sun, Dec 28
from (US$)$1,592
2026
Mon, Dec 21 - Sat, Dec 26
from (US$)$1,890
* Port changes in place on select sailings — see full cruise details

Brilliant New Year's Ahoy!

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
  • Miami, Florida
Insider cabins from
$4,302$6,432
per Cabin
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9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$4,302$6,432
per Cabin
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Departing on:
2025
Fri, Dec 26 - Sun, Jan 04
from (US$)$4,302Brilliant Lady's Inaugural Season

Resilient New Year's Ahoy!

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
$4,466$6,618
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea Terrace cabins from
$4,466$6,618
per Cabin
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Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from (US$)$4,466

Valiant New Year’s Ahoy!

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • Castries, St. Lucia
  • Bridgetown, Barbados
  • St. Croix, U.S. Virgin Islands
  • San Juan, Puerto Rico
Sea View cabins from
$3,768$5,658
per Cabin
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7 nights
Valiant Lady
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+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$3,768$5,658
per Cabin
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Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from (US$)$3,768

Scarlet New Year's Ahoy!

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,990$4,376
per Cabin
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5 nights
Scarlet Lady
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+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,990$4,376
per Cabin
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Departing on:
2026Best Rate
Wed, Dec 30 - Mon, Jan 04
from (US$)$2,990
2025
Sun, Dec 28 - Fri, Jan 02
from (US$)$3,390
* Port changes in place on select sailings — see full cruise details
★
EXTRA SAVINGS

Aruban Sights & Antiguan Nights

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Sea View cabins from
$1,664
per Cabin
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7 nights
Valiant Lady
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+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$1,664
per Cabin
Loading
Departing on:
2026Best Rate
Sat, Jan 03 - Sat, Jan 10
from (US$)$1,664
2027
Sat, Feb 06 - Sat, Feb 13
from (US$)$2,366
★
EXTRA SAVINGS

Cozumel, Grand Cayman & Bimini

  • Miami, Florida
  • George Town, Grand Cayman
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$2,940$4,214
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$2,940$4,214
per Cabin
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Departing on:
2026
Sat, Jan 03 - Sat, Jan 10
from (US$)$2,940

Aruba, Bonaire, Colombia, Jamaica & More

  • Miami, Florida
  • Oranjestad, Aruba
  • Kralendijk, Bonaire
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Sea View cabins from
$3,498$5,130
per Cabin
Loading
11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$3,498$5,130
per Cabin
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Departing on:
2026
Sun, Jan 04 - Thu, Jan 15
from (US$)$3,498Brilliant Lady's Inaugural Season

Cayman Isles & Jamaican Miles

  • Miami, Florida
  • George Town, Grand Cayman
  • Ocho Rios, Jamaica
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,946$2,746
per Cabin
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7 nights
Resilient Lady & Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$1,946$2,746
per Cabin
Loading
Departing on:
2026Best Rate
Sun, Dec 13 - Sun, Dec 20
from (US$)$1,946
2026
Sat, Jan 10 - Sat, Jan 17
from (US$)$2,226
2026
Sat, Mar 07 - Sat, Mar 14
from (US$)$2,590

Virgin Island Views & Saint Isle Blues

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Bridgetown, Barbados
  • Kingstown, St. Vincent
  • Basseterre, St. Kitts and Nevis
  • St. Croix, U.S. Virgin Islands
  • San Juan, Puerto Rico
Sea View cabins from
$2,226$3,294
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$2,226$3,294
per Cabin
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Departing on:
2026
Sat, Jan 10 - Sat, Jan 17
from (US$)$2,226

St. Kitts, Barbados, Martinique & More

  • San Juan, Puerto Rico
  • Basseterre, St. Kitts and Nevis
  • Bridgetown, Barbados
  • Fort-de-France, Martinique
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Sea View cabins from
$2,226$3,280
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off a second Sailor
Sea View cabins from
$2,226$3,280
per Cabin
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Departing on:
2026
Sat, Jan 17 - Sat, Jan 24
from (US$)$2,226

Barbados, Antigua, BVI & More

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Bridgetown, Barbados
  • Fort-de-France, Martinique
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Sea View cabins from
$2,226$3,276
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off a second Sailor
Sea View cabins from
$2,226$3,276
per Cabin
Loading
Departing on:
2026
Sat, Jan 24 - Sat, Jan 31
from (US$)$2,226

Grand Turk, Puerto Plata & Bimini

  • Miami, Florida
  • The Beach Club at Bimini, Bahamas
  • Puerto Plata, Dominican Republic
  • Grand Turk, Turks and Caicos
  • Miami, Florida
Insider cabins from
$2,160$3,096
per Cabin
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6 nights
Brilliant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,160$3,096
per Cabin
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Departing on:
2026
Mon, Jan 26 - Sun, Feb 01
from (US$)$2,160

Antigua & the St. Isles

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • St. John's, Antigua
  • Castries, St. Lucia
  • Charlotte Amalie, St. Thomas
  • San Juan, Puerto Rico
Sea View cabins from
$2,226$3,260
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off a second Sailor
Sea View cabins from
$2,226$3,260
per Cabin
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Departing on:
2026
Sat, Jan 31 - Sat, Feb 07
from (US$)$2,226
★
EXTRA SAVINGS

San Juan Sunrises & Dominican Dreams

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$2,086$2,980
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$2,086$2,980
per Cabin
Loading
Departing on:
2026Best Rate
Sat, Jan 31 - Sat, Feb 07
from (US$)$2,086
2026
Sat, Feb 28 - Sat, Mar 07
from (US$)$2,366
2026
Sun, Dec 06 - Sun, Dec 13
from (US$)$2,086

Magnetic Miami to Gorgeous George Town

  • Miami, Florida
  • Willemstad, Curaçao
  • Oranjestad, Aruba
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Sea View cabins from
$3,278$4,788
per Cabin
Loading
11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$3,278$4,788
per Cabin
Loading
Departing on:
2026
Sun, Feb 01 - Thu, Feb 12
from (US$)$3,278Brilliant Lady's Inaugural Season

St. Lucia, Barbados & More

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • Castries, St. Lucia
  • Bridgetown, Barbados
  • Charlotte Amalie, St. Thomas
  • San Juan, Puerto Rico
Sea View cabins from
$2,226$3,262
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$2,226$3,262
per Cabin
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Departing on:
2026
Sat, Feb 07 - Sat, Feb 14
from (US$)$2,226
★
EXTRA SAVINGS

Brilliant Valentine's Voyage

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • St. Croix, U.S. Virgin Islands
  • Miami, Florida
Insider cabins from
$2,544$3,718
per Cabin
Loading
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,544$3,718
per Cabin
Loading
Departing on:
2026
Thu, Feb 12 - Fri, Feb 20
from (US$)$2,544Brilliant Lady's Inaugural Season

Scarlet Valentine's Voyage

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$1,890$2,702
per Cabin
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5 nights
Scarlet Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$1,890$2,702
per Cabin
Loading
Departing on:
2026
Fri, Feb 13 - Wed, Feb 18
from (US$)$1,890
★
EXTRA SAVINGS

Resilient Valentine's Voyage

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,086$2,962
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,086$2,962
per Cabin
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Departing on:
2026
Sat, Feb 14 - Sat, Feb 21
from (US$)$2,086

Valiant Valentine's Voyage

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • St. Croix, U.S. Virgin Islands
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Sea View cabins from
$2,226$3,284
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$2,226$3,284
per Cabin
Loading
Departing on:
2026
Sat, Feb 14 - Sat, Feb 21
from (US$)$2,226

Antigua, Martinique, & Barbados & More

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Bridgetown, Barbados
  • Fort-de-France, Martinique
  • St. John's, Antigua
  • Tortola, British Virgin Islands
  • San Juan, Puerto Rico
Sea View cabins from
$2,366$3,492
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$2,366$3,492
per Cabin
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Departing on:
2026
Sat, Feb 21 - Sat, Feb 28
from (US$)$2,366

Quaint Castries to Elegant Antigua

  • San Juan, Puerto Rico
  • Basseterre, St. Kitts and Nevis
  • Castries, St. Lucia
  • Fort-de-France, Martinique
  • St. John's, Antigua
  • Tortola, British Virgin Islands
  • San Juan, Puerto Rico
Sea Terrace cabins from
$2,646$3,932
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea Terrace cabins from
$2,646$3,932
per Cabin
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Departing on:
2026
Sat, Mar 07 - Sat, Mar 14
from (US$)$2,646

Red Hot Sailing Club Voyage

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • St. John's, Antigua
  • Basseterre, St. Kitts and Nevis
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,502$3,612
per Cabin
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9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,502$3,612
per Cabin
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Departing on:
2026
Thu, Mar 12 - Sat, Mar 21
from (US$)$2,502Brilliant Lady's Inaugural Season

Costa Mayan Caves & Honduran Waves

  • Miami, Florida
  • Roatán, Honduras
  • Costa Maya, Mexico
  • Cozumel, Mexico
  • Miami, Florida
Sea View cabins from
$2,268$3,224
per Cabin
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6 nights
Resilient Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$2,268$3,224
per Cabin
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Departing on:
2026
Sat, Mar 14 - Fri, Mar 20
from (US$)$2,268

Sunsets in the Lesser Antilles

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • Fort-de-France, Martinique
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
Insider cabins from
$2,226$3,274
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,226$3,274
per Cabin
Loading
Departing on:
2026Best Rate
Sat, Dec 05 - Sat, Dec 12
from (US$)$2,226
2026
Sat, Mar 14 - Sat, Mar 21
from (US$)$3,066
2027
Sat, Jan 09 - Sat, Jan 16
from (US$)$2,226

Puerto Rican Nights & St. Croix Delights

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • St. Croix, U.S. Virgin Islands
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,960$4,316
per Cabin
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8 nights
Resilient Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,960$4,316
per Cabin
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Departing on:
2026
Fri, Mar 20 - Sat, Mar 28
from (US$)$2,960

Panama Canal & Pacific Wonders

  • Miami, Florida
  • Cartagena, Colombia
  • Colón, Panama
  • Panama Canal (Cruising), Panama
  • Puntarenas, Costa Rica
  • Puerto Quetzal, Guatemala
  • Cabo San Lucas, Mexico
  • Los Angeles, California
Insider cabins from
$6,368$9,088
per Cabin
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16 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$6,368$9,088
per Cabin
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Departing on:
2026
Sat, Mar 21 - Mon, Apr 06
from (US$)$6,368Brilliant Lady's Inaugural Season

Tortola, Charleston, Newport & More

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Puerto Plata, Dominican Republic
  • Charleston, South Carolina
  • Newport, Rhode Island
  • New York City, New York
Insider cabins from
$1,964$2,800
per Cabin
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9 nights
Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$1,964$2,800
per Cabin
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Departing on:
2026
Sat, Mar 28 - Mon, Apr 06
from (US$)$1,964

The Big Apple to Bermuda

  • New York City, New York
  • Royal Naval Dockyard, Bermuda
  • New York City, New York
Insider cabins from
$1,490$2,018
per Cabin
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5 nights
Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$1,490$2,018
per Cabin
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Departing on:
2026Best Rate
Mon, Apr 06 - Sat, Apr 11
from (US$)$1,490
2026
Sun, Sep 27 - Fri, Oct 02
from (US$)$1,690
2026
Fri, Oct 02 - Wed, Oct 07
from (US$)$1,690

Brilliant Lady LA MerMaiden

  • Los Angeles, California
  • Santa Barbara, California
  • San Diego, California
  • Ensenada, Mexico
  • Los Angeles, California
Sea View cabins from
$1,990$2,824
per Cabin
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5 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$1,990$2,824
per Cabin
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Departing on:
2026
Tue, Apr 07 - Sun, Apr 12
from (US$)$1,990Brilliant Lady's Inaugural Season

Virgin Voyages Comedy Fest New York

  • New York City, New York
  • Royal Naval Dockyard, Bermuda
  • New York City, New York
Insider cabins from
$1,590$2,172
per Cabin
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5 nights
Valiant Lady
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70% off a second Sailor
Insider cabins from
$1,590$2,172
per Cabin
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Departing on:
2026
Sat, Apr 11 - Thu, Apr 16
from (US$)$1,590

California (and Mexico) Dreamin'

  • Los Angeles, California
  • Cabo San Lucas, Mexico
  • Mazatlàn, Mexico
  • Los Angeles, California
Sea View cabins from
$2,508$3,632
per Cabin
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6 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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70% off a second Sailor
Sea View cabins from
$2,508$3,632
per Cabin
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Departing on:
2026
Sun, Apr 12 - Sat, Apr 18
from (US$)$2,508Brilliant Lady's Inaugural Season

Bermuda Beauty to East Coast Elegance

  • New York City, New York
  • Royal Naval Dockyard, Bermuda
  • Nassau, Bahamas
  • Charleston, South Carolina
  • New York City, New York
Insider cabins from
$1,962$2,672
per Cabin
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9 nights
Valiant Lady
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70% off a second Sailor
Insider cabins from
$1,962$2,672
per Cabin
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Departing on:
2026
Thu, Apr 16 - Sat, Apr 25
from (US$)$1,962

New York Transatlantic to Spain

  • New York City, New York
  • Ponta Delgada, Azores
  • Funchal, Madeira, Portugal
  • Tangier, Morocco
  • Málaga, Spain
  • Palma de Mallorca, Spain
  • Barcelona
RockStar Quarters suites from
$11,200
per Cabin
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14 nights
Valiant Lady
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70% off a second Sailor
RockStar Quarters suites from
$11,200
per Cabin
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Departing on:
2026
Sat, Apr 25 - Sat, May 09
from (US$)$11,200
Only suites remaining

Hollywood Sunsets & Mexican Horizons

  • Los Angeles, California
  • Cabo San Lucas, Mexico
  • Mazatlàn, Mexico
  • Puerto Vallarta, Mexico
  • Los Angeles, California
Insider cabins from
$1,946$2,730
per Cabin
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7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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70% off a second Sailor
Insider cabins from
$1,946$2,730
per Cabin
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Departing on:
2026Best Rate
Sat, Sep 19 - Sat, Sep 26
from (US$)$1,946
2026
Sun, Apr 26 - Sun, May 03
from (US$)$3,066Brilliant Lady's Inaugural Season
2026
Sat, Sep 26 - Sat, Oct 03
from (US$)$1,946

Transatlantic to Spain & Morocco

  • Miami, Florida
  • Las Palmas de Gran Canaria, Spain
  • Casablanca, Morocco
  • Alicante, Spain
  • Barcelona
Insider cabins from
$3,500$5,218
per Cabin
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14 nights
Scarlet Lady
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70% off a second Sailor
Insider cabins from
$3,500$5,218
per Cabin
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Departing on:
2026
Sun, Apr 26 - Sun, May 10
from (US$)$3,500

LA Lights & Vancouver Vistas

  • Los Angeles, California
  • Catalina Island, California
  • San Francisco, California
  • Astoria, Oregon
  • Victoria, British Columbia
  • Vancouver, British Columbia
Insider cabins from
$2,224$3,128
per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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70% off a second Sailor
Insider cabins from
$2,224$3,128
per Cabin
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Departing on:
2026
Sun, May 03 - Mon, May 11
from (US$)$2,224Brilliant Lady's Inaugural Season

Rome, Mykonos & the Amalfi Coast

  • Barcelona
  • Rome (Civitavecchia), Italy
  • Amalfi Coast (Salerno), Italy
  • Catania, Sicily, Italy
  • Mykonos, Greece
  • Athens (Piraeus)
Sea View cabins from
$4,620$6,860
per Cabin
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7 nights
Scarlet Lady
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70% off a second Sailor
Sea View cabins from
$4,620$6,860
per Cabin
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Departing on:
2026
Sun, May 10 - Sun, May 17
from (US$)$4,620

Alaska Awe from Vancouver to Seattle

  • Vancouver, British Columbia
  • Inside Passage (Cruising), Alaska
  • Ketchikan, Alaska
  • Sitka, Alaska
  • Hubbard Glacier (Cruising), Alaska
  • Skagway, Alaska
  • Juneau, Alaska
  • Icy Strait Point, Alaska
  • Seattle, Washington
Insider cabins from
$3,580$5,200
per Cabin
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10 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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70% off a second Sailor
Insider cabins from
$3,580$5,200
per Cabin
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Departing on:
2026
Mon, May 11 - Thu, May 21
from (US$)$3,580Brilliant Lady's Inaugural Season

Brilliant Lady Seattle MerMaiden

  • Seattle, Washington
  • Inside Passage (Cruising), Alaska
  • Ketchikan, Alaska
  • Sitka, Alaska
  • Tracy Arm Fjord (Cruising), Alaska
  • Prince Rupert, British Columbia
  • Seattle, Washington
Insider cabins from
$2,646$3,758
per Cabin
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7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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70% off a second Sailor
Insider cabins from
$2,646$3,758
per Cabin
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Departing on:
2026
Thu, May 21 - Thu, May 28
from (US$)$2,646Brilliant Lady's Inaugural Season

Corfu, Dubrovnik & More

  • Athens (Piraeus)
  • Kotor, Montenegro
  • Dubrovnik, Croatia
  • Corfu, Greece
  • Mykonos, Greece
  • Athens (Piraeus)
Insider cabins from
$3,360$4,924
per Cabin
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7 nights
Scarlet Lady
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70% off a second Sailor
Insider cabins from
$3,360$4,924
per Cabin
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Departing on:
2026
Sun, May 24 - Sun, May 31
from (US$)$3,360

Amalfi Coast, Cannes & Ibiza

  • Rome (Civitavecchia)
  • Amalfi Coast (Salerno), Italy
  • Cannes, France
  • Ibiza, Spain
  • Barcelona
Insider cabins from
$3,300$4,900
per Cabin
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6 nights
Valiant Lady
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70% off a second Sailor
Insider cabins from
$3,300$4,900
per Cabin
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Departing on:
2026
Mon, May 25 - Sun, May 31
from (US$)$3,300

Seattle, Juneau & Canadian Coasts

  • Seattle, Washington
  • Inside Passage (Cruising), Alaska
  • Ketchikan, Alaska
  • Juneau, Alaska
  • Tracy Arm Fjord (Cruising), Alaska
  • Prince Rupert, British Columbia
  • Seattle, Washington
Sea View cabins from
$3,066$4,390
per Cabin
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7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$3,066$4,390
per Cabin
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Departing on:
2026Best Rate
Thu, Aug 20 - Thu, Aug 27
from (US$)$3,066Brilliant Lady's Inaugural Season
2026
Thu, May 28 - Thu, Jun 04
from (US$)$3,346Brilliant Lady's Inaugural Season

Spanish Isles, Rome & Cannes

  • Barcelona
  • Palma de Mallorca, Spain
  • Rome (Civitavecchia), Italy
  • Cannes, France
  • Ibiza, Spain
  • Barcelona
Insider cabins from
$3,150$4,628
per Cabin
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7 nights
Valiant Lady
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70% off a second Sailor
Insider cabins from
$3,150$4,628
per Cabin
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Departing on:
2026
Sun, May 31 - Sun, Jun 07
from (US$)$3,150

Alaskan Glacier Blues & Coastal Views

  • Seattle, Washington
  • Inside Passage (Cruising), Alaska
  • Ketchikan, Alaska
  • Sitka, Alaska
  • Tracy Arm Fjord (Cruising), Alaska
  • Prince Rupert, British Columbia
  • Seattle, Washington
Insider cabins from
$2,646$3,758
per Cabin
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7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,646$3,758
per Cabin
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Departing on:
2026Best Rate
Thu, Jul 16 - Thu, Jul 23
from (US$)$2,646Brilliant Lady's Inaugural Season
2026
Thu, Jun 04 - Thu, Jun 11
from (US$)$2,926Brilliant Lady's Inaugural Season
2026
Thu, Jul 02 - Thu, Jul 09
from (US$)$3,500Brilliant Lady's Inaugural Season

Coastal Gems: Italy, France & Spain

  • Barcelona
  • Provence (Toulon), France
  • Tuscany/Cinque Terre (Marina di Carrara), Italy
  • Ajaccio, Corsica, France
  • Ibiza, Spain
  • Barcelona
Sea Terrace cabins from
$2,786$4,074
per Cabin
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7 nights
Valiant Lady
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70% off a second Sailor
Sea Terrace cabins from
$2,786$4,074
per Cabin
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Departing on:
2026
Sun, Jun 07 - Sun, Jun 14
from (US$)$2,786

Cayman Isles & Bimini Beach Miles

  • Miami, Florida
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,440$1,938
per Cabin
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5 nights
Resilient Lady, Scarlet Lady & Valiant Lady
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70% off a second Sailor
Insider cabins from
$1,440$1,938
per Cabin
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Departing on:
2027Best Rate
Mon, Aug 30 - Sat, Sep 04
from (US$)$1,440
2026
Mon, Jun 08 - Sat, Jun 13
from (US$)$1,890
2026
Sat, Jun 13 - Thu, Jun 18
from (US$)$2,190

Inside Passage Alaska & Canadian Coasts

  • Seattle, Washington
  • Inside Passage (Cruising), Alaska
  • Ketchikan, Alaska
  • Sitka, Alaska
  • Hubbard Glacier (Cruising), Alaska
  • Skagway, Alaska
  • Icy Strait Point, Alaska
  • Haines, Alaska
  • Prince Rupert, British Columbia
  • Victoria, British Columbia
  • Seattle, Washington
Insider cabins from
$5,256$7,654
per Cabin
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12 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$5,256$7,654
per Cabin
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Departing on:
2026
Thu, Jun 11 - Tue, Jun 23
from (US$)$5,256Brilliant Lady's Inaugural Season

Spanish Serenity to French Daydreams

  • Barcelona
  • Palma de Mallorca, Spain
  • Valencia, Spain
  • Cannes, France
  • Ibiza, Spain
  • Barcelona
Sea View cabins from
$3,066$4,500
per Cabin
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7 nights
Valiant Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$3,066$4,500
per Cabin
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Departing on:
2026
Sun, Jun 14 - Sun, Jun 21
from (US$)$3,066

Italian Vistas to Spanish Sunsets

  • Barcelona
  • Rome (Civitavecchia), Italy
  • Tuscany/Cinque Terre (La Spezia), Italy
  • Cannes, France
  • Ibiza, Spain
  • Barcelona
Insider cabins from
$3,080$4,530
per Cabin
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7 nights
Valiant Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$3,080$4,530
per Cabin
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Departing on:
2026
Sun, Jun 21 - Sun, Jun 28
from (US$)$3,080

Alaskan Inside Passage & Canadian Coasts

  • Seattle, Washington
  • Inside Passage (Cruising), Alaska
  • Ketchikan, Alaska
  • Icy Strait Point, Alaska
  • Hubbard Glacier (Cruising), Alaska
  • Sitka, Alaska
  • Victoria, British Columbia
  • Seattle, Washington
Insider cabins from
$3,942$5,728
per Cabin
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9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$3,942$5,728
per Cabin
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Departing on:
2026
Tue, Jun 23 - Thu, Jul 02
from (US$)$3,942Brilliant Lady's Inaugural Season

Istanbul Delights & Santorini Dreams

  • Athens (Piraeus)
  • Istanbul, Turkey
  • Ephesus (Kuşadasi), Turkey
  • Mykonos, Greece
  • Rhodes, Greece
  • Santorini, Greece
  • Chania (Souda Bay), Crete, Greece
  • Athens (Piraeus)
Sea View cabins from
$5,060$7,402
per Cabin
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11 nights
Scarlet Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$5,060$7,402
per Cabin
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Departing on:
2026
Wed, Jun 24 - Sun, Jul 05
from (US$)$5,060

Riviera Charms, Rome & Corsica

  • Barcelona
  • Nice (Villefranche), France
  • Rome (Civitavecchia), Italy
  • Ajaccio, Corsica, France
  • Ibiza, Spain
  • Barcelona
Sea View cabins from
$3,192$4,686
per Cabin
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6 nights
Valiant Lady
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70% off a second Sailor
Sea View cabins from
$3,192$4,686
per Cabin
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Departing on:
2026
Sun, Jun 28 - Sat, Jul 04
from (US$)$3,192

French Riviera, Italy, Rome & Ibiza

  • Barcelona
  • Rome (Civitavecchia), Italy
  • Florence/Pisa (Livorno), Italy
  • Cannes, France
  • Ibiza, Spain
  • Barcelona
Sea View cabins from
$3,570$5,264
per Cabin
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7 nights
Valiant Lady
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70% off a second Sailor
Sea View cabins from
$3,570$5,264
per Cabin
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Departing on:
2026
Sat, Jul 04 - Sat, Jul 11
from (US$)$3,570

French Riviera, Rome, Amalfi & Sicily

  • Barcelona
  • Provence (Marseille), France
  • Nice (Villefranche), France
  • Rome (Civitavecchia), Italy
  • Amalfi Coast (Salerno), Italy
  • Catania, Sicily, Italy
  • Palermo, Sicily, Italy
  • Barcelona
Sea View cabins from
$4,480$6,642
per Cabin
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8 nights
Valiant Lady
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70% off a second Sailor
Sea View cabins from
$4,480$6,642
per Cabin
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Departing on:
2026
Sat, Jul 11 - Sun, Jul 19
from (US$)$4,480

Tuscany, Corsica & Ibiza

  • Barcelona
  • Provence (Toulon), France
  • Florence/Pisa (Livorno), Italy
  • Ajaccio, Corsica, France
  • Ibiza, Spain
  • Barcelona
Sea View cabins from
$2,436$3,530
per Cabin
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7 nights
Valiant Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Sea View cabins from
$2,436$3,530
per Cabin
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Departing on:
2026
Sun, Jul 19 - Sun, Jul 26
from (US$)$2,436

Rome, Florence, Corsica & Ibiza

  • Barcelona
  • Palma de Mallorca, Spain
  • Cannes, France
  • Rome (Civitavecchia), Italy
  • Florence/Pisa (Livorno), Italy
  • Ajaccio, Corsica, France
  • Ibiza, Spain
  • Barcelona
Insider cabins from
$3,222$4,712
per Cabin
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9 nights
Scarlet Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$3,222$4,712
per Cabin
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Departing on:
2026
Fri, Jul 24 - Sun, Aug 02
from (US$)$3,222

Moroccan Marvels & Mediterranean Wonders

  • Barcelona
  • Tangier, Morocco
  • Lisbon, Portugal
  • La Coruña, Spain
  • Bilbao, Spain
  • Bordeaux (Le Verdon), France
  • Portsmouth
Insider cabins from
$3,900$5,744
per Cabin
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10 nights
Valiant Lady
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70% off a second Sailor
Insider cabins from
$3,900$5,744
per Cabin
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Departing on:
2026
Sun, Jul 26 - Wed, Aug 05
from (US$)$3,900

Spanish, French & Italian Classics

  • Barcelona
  • Palma de Mallorca, Spain
  • Provence (Marseille), France
  • Cannes, France
  • Ajaccio, Corsica, France
  • Tuscany/Cinque Terre (La Spezia), Italy
  • Barcelona
Insider cabins from
$3,440$5,060
per Cabin
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8 nights
Scarlet Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$3,440$5,060
per Cabin
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Departing on:
2026
Sun, Aug 02 - Mon, Aug 10
from (US$)$3,440

Eclipse in the Land of Fire and Ice

  • Portsmouth
  • Dublin, Ireland
  • Glasgow (Greenock), Scotland
  • Liverpool, United Kingdom
  • Belfast, Northern Ireland
  • Siglufjörður, Iceland
  • Ísafjörður, Iceland
  • Reykjavik, Iceland
  • Edinburgh, Scotland
  • Portsmouth
Insider cabins from
$8,700$12,790
per Cabin
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15 nights
Valiant Lady
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70% off a second Sailor
Insider cabins from
$8,700$12,790
per Cabin
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Departing on:
2026
Wed, Aug 05 - Thu, Aug 20
from (US$)$8,700

Total Eclipse of the (Med)

  • Barcelona
  • Palma de Mallorca, Spain
  • Ibiza, Spain
  • Cannes, France
  • Ajaccio, Corsica, France
  • Tuscany/Cinque Terre (La Spezia), Italy
  • Amalfi Coast (Salerno), Italy
  • Catania, Sicily, Italy
  • Rome (Civitavecchia)
Insider cabins from
$7,200$10,844
per Cabin
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12 nights
Scarlet Lady
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70% off a second Sailor
Insider cabins from
$7,200$10,844
per Cabin
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Departing on:
2026
Mon, Aug 10 - Sat, Aug 22
from (US$)$7,200

Virgin Voyages Comedy Fest from the UK

  • Portsmouth
  • Bruges/Zeebruge (Brussels), Belgium
  • Amsterdam, Netherlands
  • Hamburg, Germany
  • Portsmouth
Sea View cabins from
$3,360$4,872
per Cabin
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7 nights
Valiant Lady
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70% off a second Sailor
Sea View cabins from
$3,360$4,872
per Cabin
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Departing on:
2026
Thu, Aug 20 - Thu, Aug 27
from (US$)$3,360

Sicily, Naples, Cannes & More

  • Rome (Civitavecchia)
  • Catania, Sicily, Italy
  • Pompeii/Capri (Naples), Italy
  • Ajaccio, Corsica, France
  • Cannes, France
  • Florence/Pisa (Livorno), Italy
  • Rome (Civitavecchia)
Insider cabins from
$3,044$4,510
per Cabin
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9 nights
Scarlet Lady
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70% off a second Sailor
Insider cabins from
$3,044$4,510
per Cabin
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Departing on:
2026
Sat, Aug 22 - Mon, Aug 31
from (US$)$3,044

English Elegance to Idyllic Iceland

  • Portsmouth
  • Amsterdam, Netherlands
  • Edinburgh, Scotland
  • Invergordon, Scotland
  • Akureyri, Iceland
  • Ísafjörður, Iceland
  • Reykjavik
Insider cabins from
$3,780$5,322
per Cabin
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10 nights
Valiant Lady
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70% off a second Sailor
Insider cabins from
$3,780$5,322
per Cabin
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Departing on:
2026
Thu, Aug 27 - Sun, Sep 06
from (US$)$3,780

Rome, Florence, Mykonos & More

  • Rome (Civitavecchia)
  • Florence/Pisa (Livorno), Italy
  • Amalfi Coast (Salerno), Italy
  • Catania, Sicily, Italy
  • Chania (Souda Bay), Crete, Greece
  • Santorini, Greece
  • Mykonos, Greece
  • Athens (Piraeus)
Insider cabins from
$5,100$7,596
per Cabin
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10 nights
Scarlet Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$5,100$7,596
per Cabin
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Departing on:
2026
Mon, Aug 31 - Thu, Sep 10
from (US$)$5,100

Seattle to Alaska & British Columbia

  • Seattle, Washington
  • Sitka, Alaska
  • Icy Strait Point, Alaska
  • Skagway, Alaska
  • Tracy Arm Fjord (Cruising), Alaska
  • Ketchikan, Alaska
  • Vancouver, British Columbia
Insider cabins from
$2,704$3,816
per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,704$3,816
per Cabin
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Departing on:
2026
Thu, Sep 03 - Fri, Sep 11
from (US$)$2,704Brilliant Lady's Inaugural Season

Iceland, Greenland, Canada & NYC

  • Reykjavik
  • Ísafjörður, Iceland
  • Prince Christian Sound (Cruising), Greenland
  • Qaqortoq, Greenland
  • Nuuk, Greenland
  • St. John's, Newfoundland
  • Halifax, Nova Scotia
  • New York City, New York
Insider cabins from
$4,810$7,008
per Cabin
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13 nights
Valiant Lady
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70% off a second Sailor
Insider cabins from
$4,810$7,008
per Cabin
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Departing on:
2026
Sun, Sep 06 - Sat, Sep 19
from (US$)$4,810

Vancouver Down the Cali Coast

  • Vancouver, British Columbia
  • Astoria, Oregon
  • San Francisco, California
  • Santa Barbara, California
  • Catalina Island, California
  • San Diego, California
  • Los Angeles, California
Sea View cabins from
$2,704$3,854
per Cabin
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8 nights
Brilliant Lady
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70% off a second Sailor
Sea View cabins from
$2,704$3,854
per Cabin
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Departing on:
2026
Fri, Sep 11 - Sat, Sep 19
from (US$)$2,704

Fall Foliage in Canada & New England

  • New York City, New York
  • Boston, Massachusetts
  • Portland, Maine
  • Saint John, New Brunswick
  • Halifax, Nova Scotia
  • New York City, New York
Insider cabins from
$2,544$3,548
per Cabin
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8 nights
Valiant Lady
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70% off a second Sailor
Insider cabins from
$2,544$3,548
per Cabin
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Departing on:
2026
Sat, Sep 19 - Sun, Sep 27
from (US$)$2,544

Mykonos Moons and Italian Sunrises

  • Athens (Piraeus)
  • Mykonos, Greece
  • Catania, Sicily, Italy
  • Amalfi Coast (Salerno), Italy
  • Rome (Civitavecchia), Italy
  • Barcelona
Insider cabins from
$3,430$5,032
per Cabin
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7 nights
Scarlet Lady
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70% off a second Sailor
Insider cabins from
$3,430$5,032
per Cabin
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Departing on:
2026
Sun, Oct 04 - Sun, Oct 11
from (US$)$3,430

New York to Bermuda (& Back)

  • New York City, New York
  • Royal Naval Dockyard, Bermuda
  • New York City, New York
Insider cabins from
$2,028$2,836
per Cabin
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6 nights
Valiant Lady
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70% off a second Sailor
Insider cabins from
$2,028$2,836
per Cabin
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Departing on:
2026Best Rate
Wed, Oct 07 - Tue, Oct 13
from (US$)$2,028
2026
Tue, Oct 13 - Mon, Oct 19
from (US$)$2,268

Spanish Isles & Transatlantic Miles

  • Barcelona
  • Casablanca, Morocco
  • Las Palmas de Gran Canaria, Spain
  • Santa Cruz de Tenerife, Spain
  • Miami, Florida
Insider cabins from
$3,222$4,806
per Cabin
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14 nights
Scarlet Lady
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70% off a second Sailor
Insider cabins from
$3,222$4,806
per Cabin
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Departing on:
2026
Sun, Oct 11 - Sun, Oct 25
from (US$)$3,222

NY to San Juan: Bermuda & Caribbean

  • New York City, New York
  • Royal Naval Dockyard, Bermuda
  • The Beach Club at Bimini, Bahamas
  • St. Croix, U.S. Virgin Islands
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • San Juan, Puerto Rico
Insider cabins from
$2,856$4,016
per Cabin
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12 nights
Valiant Lady
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70% off a second Sailor
Insider cabins from
$2,856$4,016
per Cabin
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Departing on:
2026
Mon, Oct 19 - Sat, Oct 31
from (US$)$2,856

SoCal & Ensenada: Halloween Edition

  • Los Angeles, California
  • Catalina Island, California
  • San Diego, California
  • Ensenada, Mexico
  • Los Angeles, California
Sea View cabins from
$1,490$2,040
per Cabin
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5 nights
Brilliant Lady
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70% off a second Sailor
Sea View cabins from
$1,490$2,040
per Cabin
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Departing on:
2026
Sat, Oct 24 - Thu, Oct 29
from (US$)$1,490

Miami to Grand Turk: Halloween Edition

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,040$2,904
per Cabin
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6 nights
Scarlet Lady
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70% off a second Sailor
Insider cabins from
$2,040$2,904
per Cabin
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Departing on:
2026
Sun, Oct 25 - Sat, Oct 31
from (US$)$2,040

Mexico & Bimini: Halloween Edition

  • Miami, Florida
  • Cozumel, Mexico
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,908$2,660
per Cabin
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6 nights
Resilient Lady
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70% off a second Sailor
Insider cabins from
$1,908$2,660
per Cabin
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Departing on:
2026
Mon, Oct 26 - Sun, Nov 01
from (US$)$1,908

Picturesque Panama Canal Collective

  • Los Angeles, California
  • Cabo San Lucas, Mexico
  • Puerto Quetzal, Guatemala
  • Puntarenas, Costa Rica
  • Panama City, Panama
  • Panama Canal (Cruising), Panama
  • Cartagena, Colombia
  • Miami, Florida
Insider cabins from
$4,726$6,436
per Cabin
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17 nights
Brilliant Lady
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70% off a second Sailor
Insider cabins from
$4,726$6,436
per Cabin
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Departing on:
2026
Thu, Oct 29 - Sun, Nov 15
from (US$)$4,726

Scarlet's Haunted Halloween Soirée

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,590$2,176
per Cabin
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5 nights
Scarlet Lady
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70% off a second Sailor
Insider cabins from
$1,590$2,176
per Cabin
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Departing on:
2026
Sat, Oct 31 - Thu, Nov 05
from (US$)$1,590

Valiant's Haunted Halloween Soirée

  • San Juan, Puerto Rico
  • Willemstad, Curaçao
  • Oranjestad, Aruba
  • Fort-de-France, Martinique
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
Insider cabins from
$2,366$3,490
per Cabin
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7 nights
Valiant Lady
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70% off a second Sailor
Insider cabins from
$2,366$3,490
per Cabin
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Departing on:
2026
Sat, Oct 31 - Sat, Nov 07
from (US$)$2,366

November Nights in the Eastern Caribbean

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,384$3,410
per Cabin
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8 nights
Resilient Lady
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70% off a second Sailor
Insider cabins from
$2,384$3,410
per Cabin
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Departing on:
2026
Sun, Nov 08 - Mon, Nov 16
from (US$)$2,384

Caribbean East: Virgin & Saint Isles

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Basseterre, St. Kitts and Nevis
  • St. John's, Antigua
  • Castries, St. Lucia
  • San Juan, Puerto Rico
Insider cabins from
$1,908$2,618
per Cabin
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6 nights
Valiant Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$1,908$2,618
per Cabin
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Departing on:
2027Best Rate
Sat, Jan 23 - Fri, Jan 29
from (US$)$1,908
2026
Sat, Nov 14 - Fri, Nov 20
from (US$)$2,028
2027
Sat, Mar 13 - Fri, Mar 19
from (US$)$2,148

St. Isles & Sun-soaked Seas

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • Basseterre, St. Kitts and Nevis
  • St. John's, Antigua
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,580$3,602
per Cabin
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10 nights
Brilliant Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,580$3,602
per Cabin
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Departing on:
2027Best Rate
Mon, Jan 25 - Thu, Feb 04
from (US$)$2,580
2026
Sun, Nov 15 - Wed, Nov 25
from (US$)$3,180
2027
Mon, Feb 22 - Thu, Mar 04
from (US$)$2,780

Captivating Costa Maya & Cozumel Charm

  • Miami, Florida
  • Costa Maya, Mexico
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,788$2,476
per Cabin
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6 nights
Resilient Lady
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70% off a second Sailor
Insider cabins from
$1,788$2,476
per Cabin
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Departing on:
2026
Mon, Nov 16 - Sun, Nov 22
from (US$)$1,788

Thanksgiving: St. Isles, Aruba & Curaçao

  • San Juan, Puerto Rico
  • Charlotte Amalie, St. Thomas
  • Willemstad, Curaçao
  • Oranjestad, Aruba
  • Basseterre, St. Kitts and Nevis
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
$2,864$4,226
per Cabin
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8 nights
Valiant Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,864$4,226
per Cabin
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Departing on:
2026
Fri, Nov 20 - Sat, Nov 28
from (US$)$2,864

Jamaican Waves & Bimini Breeze

  • Miami, Florida
  • Ocho Rios, Jamaica
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,590$2,152
per Cabin
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5 nights
Scarlet Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$1,590$2,152
per Cabin
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Departing on:
2027Best Rate
Mon, Feb 15 - Sat, Feb 20
from (US$)$1,590
2026
Mon, Nov 23 - Sat, Nov 28
from (US$)$1,790

Antiguan Elegance & Sunny St. Isles

  • San Juan, Puerto Rico
  • Charlotte Amalie, St. Thomas
  • Tortola, British Virgin Islands
  • Basseterre, St. Kitts and Nevis
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
$2,366$3,422
per Cabin
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7 nights
Valiant Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,366$3,422
per Cabin
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Departing on:
2026
Sat, Nov 28 - Sat, Dec 05
from (US$)$2,366

St. Maarten, Tortola, San Juan & more

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • St. Croix, U.S. Virgin Islands
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,580$3,584
per Cabin
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10 nights
Brilliant Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,580$3,584
per Cabin
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Departing on:
2027Best Rate
Mon, Jan 11 - Thu, Jan 21
from (US$)$2,580
2026
Mon, Nov 30 - Thu, Dec 10
from (US$)$3,180
2027
Mon, Mar 08 - Thu, Mar 18
from (US$)$2,980

Pre-Holiday Caribbean Getaway

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • San Juan, Puerto Rico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,142$3,040
per Cabin
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9 nights
Brilliant Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,142$3,040
per Cabin
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Departing on:
2026
Mon, Dec 14 - Wed, Dec 23
from (US$)$2,142

Valiant Caribbean Holidays

  • San Juan, Puerto Rico
  • Basseterre, St. Kitts and Nevis
  • Fort-de-France, Martinique
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • San Juan, Puerto Rico
Insider cabins from
$2,786$4,136
per Cabin
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7 nights
Valiant Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,786$4,136
per Cabin
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Departing on:
2026
Sat, Dec 19 - Sat, Dec 26
from (US$)$2,786

Resilient Caribbean Holidays

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,646$3,834
per Cabin
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7 nights
Resilient Lady
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70% off a second Sailor
Insider cabins from
$2,646$3,834
per Cabin
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Departing on:
2026
Sun, Dec 20 - Sun, Dec 27
from (US$)$2,646

Brilliant Caribbean Holidays

  • Miami, Florida
  • The Beach Club at Bimini, Bahamas
  • Puerto Plata, Dominican Republic
  • Miami, Florida
Insider cabins from
$2,090$3,002
per Cabin
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5 nights
Brilliant Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,090$3,002
per Cabin
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Departing on:
2026
Wed, Dec 23 - Mon, Dec 28
from (US$)$2,090

Valiant New Year's Ahoy!

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Fort-de-France, Martinique
  • Bridgetown, Barbados
  • Castries, St. Lucia
  • St. John's, Antigua
  • San Juan, Puerto Rico
Insider cabins from
$4,186$6,274
per Cabin
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7 nights
Valiant Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$4,186$6,274
per Cabin
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Departing on:
2026
Sat, Dec 26 - Sat, Jan 02
from (US$)$4,186

Resilient New Year's Ahoy!

  • Miami, Florida
  • George Town, Grand Cayman
  • Ocho Rios, Jamaica
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$3,766$5,546
per Cabin
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7 nights
Resilient Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$3,766$5,546
per Cabin
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Departing on:
2026
Sun, Dec 27 - Sun, Jan 03
from (US$)$3,766

Brilliant New Year's Ahoy!

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • Tortola, British Virgin Islands
  • St. John's, Antigua
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$5,180$7,702
per Cabin
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10 nights
Brilliant Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$5,180$7,702
per Cabin
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Departing on:
2026
Mon, Dec 28 - Thu, Jan 07
from (US$)$5,180

Cayman Isles & Jamaican Miles

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,086$2,892
per Cabin
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7 nights
Resilient Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,086$2,892
per Cabin
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Departing on:
2027
Sun, Jan 17 - Sun, Jan 24
from (US$)$2,086

Puerto Rico to Aruba, Bonaire & More

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • Kralendijk, Bonaire
  • Fort-de-France, Martinique
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
$2,704$3,894
per Cabin
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8 nights
Valiant Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,704$3,894
per Cabin
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Departing on:
2027
Fri, Jan 29 - Sat, Feb 06
from (US$)$2,704

San Juan & St. Isles: Valentine’s Voyage

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • St. Croix, U.S. Virgin Islands
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,780$3,892
per Cabin
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10 nights
Brilliant Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,780$3,892
per Cabin
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Departing on:
2027
Mon, Feb 08 - Thu, Feb 18
from (US$)$2,780

Key West & Bimini: Valentine’s Voyage

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,352$1,818
per Cabin
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4 nights
Scarlet Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$1,352$1,818
per Cabin
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Departing on:
2027
Thu, Feb 11 - Mon, Feb 15
from (US$)$1,352

Lesser Antilles: Valentine's Day

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • Fort-de-France, Martinique
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
Insider cabins from
$2,506$3,620
per Cabin
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7 nights
Valiant Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,506$3,620
per Cabin
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Departing on:
2027
Sat, Feb 13 - Sat, Feb 20
from (US$)$2,506

PR, DR & Bimini: Valentine’s Voyage

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,590$3,676
per Cabin
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7 nights
Resilient Lady
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+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,590$3,676
per Cabin
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Departing on:
2027
Sun, Feb 14 - Sun, Feb 21
from (US$)$2,590

Saint Isles & The Greater Antilles

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Castries, St. Lucia
  • Bridgetown, Barbados
  • Roseau, Dominica
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
$2,366$3,392
per Cabin
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7 nights
Valiant Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,366$3,392
per Cabin
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Departing on:
2027
Sat, Feb 20 - Sat, Feb 27
from (US$)$2,366

Saint (Isles) & Seas of the Caribbean

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Bridgetown, Barbados
  • Castries, St. Lucia
  • St. John's, Antigua
  • Tortola, British Virgin Islands
  • San Juan, Puerto Rico
Insider cabins from
$2,366$3,380
per Cabin
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7 nights
Valiant Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,366$3,380
per Cabin
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Departing on:
2027
Sat, Mar 06 - Sat, Mar 13
from (US$)$2,366

Barbados, Dominica & St. Isle Spring

  • San Juan, Puerto Rico
  • Charlotte Amalie, St. Thomas
  • Bridgetown, Barbados
  • Kingstown, St. Vincent
  • Roseau, Dominica
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
$2,864$4,156
per Cabin
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8 nights
Valiant Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,864$4,156
per Cabin
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Departing on:
2027
Fri, Mar 19 - Sat, Mar 27
from (US$)$2,864

Colorful Curaçao, Aruba & Antigua

  • San Juan, Puerto Rico
  • Willemstad, Curaçao
  • Oranjestad, Aruba
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Sea Terrace cabins from
$4,480$6,644
per Cabin
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Valiant Lady
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70% off a second Sailor
Sea Terrace cabins from
$4,480$6,644
per Cabin
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Departing on:
2027
Sat, Mar 27 - Sat, Apr 03
from (US$)$4,480

San Juan to Miami: Dominican Daze

  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,490$2,052
per Cabin
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5 nights
Valiant Lady
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70% off a second Sailor
Insider cabins from
$1,490$2,052
per Cabin
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Departing on:
2027
Sat, Apr 10 - Thu, Apr 15
from (US$)$1,490

Grand Cayman & Bimini Beach Club

  • Miami, Florida
  • The Beach Club at Bimini, Bahamas
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
$1,540$2,150
per Cabin
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5 nights
Resilient Lady
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70% off a second Sailor
Insider cabins from
$1,540$2,150
per Cabin
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Departing on:
2027
Fri, Apr 23 - Wed, Apr 28
from (US$)$1,540

Transatlantic Miami to Morocco & Spain

  • Miami, Florida
  • Las Palmas de Gran Canaria, Spain
  • Casablanca, Morocco
  • Valencia, Spain
  • Barcelona
Insider cabins from
$2,800$4,110
per Cabin
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14 nights
Scarlet Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,800$4,110
per Cabin
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Departing on:
2027
Sat, Apr 24 - Sat, May 08
from (US$)$2,800

Spain & Morocco Transatlantic

  • Miami, Florida
  • Santa Cruz de Tenerife, Spain
  • Tangier, Morocco
  • Málaga, Spain
  • Barcelona
Insider cabins from
$2,800$4,032
per Cabin
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14 nights
Resilient Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,800$4,032
per Cabin
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Departing on:
2027
Sun, May 02 - Sun, May 16
from (US$)$2,800

Barcelona to Amalfi, Sicily & Greece

  • Barcelona
  • Ajaccio, Corsica, France
  • Rome (Civitavecchia), Italy
  • Amalfi Coast (Salerno), Italy
  • Catania, Sicily, Italy
  • Mykonos, Greece
  • Athens (Piraeus)
Insider cabins from
$4,160$6,128
per Cabin
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8 nights
Scarlet Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$4,160$6,128
per Cabin
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Departing on:
2027
Sat, May 08 - Sun, May 16
from (US$)$4,160

French Riviera, Spain & Ibiza Overnight

  • Barcelona
  • Cannes, France
  • Provence (Toulon), France
  • Valencia, Spain
  • Ibiza, Spain
  • Barcelona
Insider cabins from
$2,786$4,040
per Cabin
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7 nights
Resilient Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,786$4,040
per Cabin
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Departing on:
2027Best Rate
Sun, Oct 03 - Sun, Oct 10
from (US$)$2,786
2027
Sun, May 16 - Sun, May 23
from (US$)$3,066
2027
Sun, May 30 - Sun, Jun 06
from (US$)$2,856

Greek Island Hues & Turkish Views

  • Athens (Piraeus)
  • Santorini, Greece
  • Chania (Souda Bay), Crete, Greece
  • Ephesus (Kuşadasi), Turkey
  • Mykonos, Greece
  • Athens (Piraeus)
Insider cabins from
$3,066$4,334
per Cabin
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7 nights
Scarlet Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$3,066$4,334
per Cabin
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Departing on:
2027Best Rate
Sun, May 16 - Sun, May 23
from (US$)$3,066
2027
Sun, Jun 06 - Sun, Jun 13
from (US$)$3,066
2027
Sun, Jul 04 - Sun, Jul 11
from (US$)$3,206

Italy, Spain & French Riviera

  • Barcelona
  • Nice (Villefranche), France
  • Rome (Civitavecchia), Italy
  • Amalfi Coast (Salerno), Italy
  • Catania, Sicily, Italy
  • Palma de Mallorca, Spain
  • Barcelona
Insider cabins from
$2,926$4,242
per Cabin
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7 nights
Resilient Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,926$4,242
per Cabin
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Departing on:
2027Best Rate
Sun, May 23 - Sun, May 30
from (US$)$2,926
2027
Sun, Sep 12 - Sun, Sep 19
from (US$)$2,926

Croatia, Montenegro, Greece & Albania

  • Athens (Piraeus)
  • Dubrovnik, Croatia
  • Kotor, Montenegro
  • Sarandë, Albania
  • Mykonos, Greece
  • Athens (Piraeus)
Insider cabins from
$2,926$4,236
per Cabin
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7 nights
Scarlet Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,926$4,236
per Cabin
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Departing on:
2027Best Rate
Sun, Aug 15 - Sun, Aug 22
from (US$)$2,926
2027
Sun, May 30 - Sun, Jun 06
from (US$)$3,206
2027
Sun, Jun 20 - Sun, Jun 27
from (US$)$3,500

Western Med: Barcelona to Athens

  • Barcelona
  • Cannes, France
  • Rome (Civitavecchia), Italy
  • Amalfi Coast (Salerno), Italy
  • Valletta, Malta
  • Chania (Souda Bay), Crete, Greece
  • Mykonos, Greece
  • Athens (Piraeus)
Insider cabins from
$3,980$5,832
per Cabin
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10 nights
Resilient Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$3,980$5,832
per Cabin
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Departing on:
2027
Sun, Jun 06 - Wed, Jun 16
from (US$)$3,980

Western Med: Athens to Barcelona

  • Athens (Piraeus)
  • Mykonos, Greece
  • Kotor, Montenegro
  • Catania, Sicily, Italy
  • Amalfi Coast (Salerno), Italy
  • Tuscany/Cinque Terre (La Spezia), Italy
  • Cannes, France
  • Provence (Marseille), France
  • Barcelona
Insider cabins from
$4,268$6,250
per Cabin
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11 nights
Resilient Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$4,268$6,250
per Cabin
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Departing on:
2027
Wed, Jun 16 - Sun, Jun 27
from (US$)$4,268

French Riviera, Spain & Ibiza Overnight

  • Barcelona
  • Nice (Villefranche), France
  • Provence (Toulon), France
  • Valencia, Spain
  • Ibiza, Spain
  • Barcelona
Insider cabins from
$2,856$4,140
per Cabin
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7 nights
Resilient Lady
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+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,856$4,140
per Cabin
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Departing on:
2027
Sun, Jun 27 - Sun, Jul 04
from (US$)$2,856

Italy, Spain & French Riviera

  • Barcelona
  • Tuscany/Cinque Terre (La Spezia), Italy
  • Rome (Civitavecchia), Italy
  • Ajaccio, Corsica, France
  • Provence (Marseille), France
  • Palma de Mallorca, Spain
  • Barcelona
Insider cabins from
$2,786$4,030
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,786$4,030
per Cabin
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Departing on:
2027Best Rate
Sun, Sep 26 - Sun, Oct 03
from (US$)$2,786
2027
Sun, Jul 04 - Sun, Jul 11
from (US$)$2,926
2027
Sun, Oct 17 - Sun, Oct 24
from (US$)$2,786

Greek Isle Days & Istanbul Nights

  • Athens (Piraeus)
  • Chania (Souda Bay), Crete, Greece
  • Rhodes, Greece
  • Mykonos, Greece
  • Ephesus (Kuşadasi), Turkey
  • Istanbul, Turkey
  • Santorini, Greece
  • Athens (Piraeus)
Insider cabins from
$5,280$7,684
per Cabin
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11 nights
Scarlet Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$5,280$7,684
per Cabin
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Departing on:
2027
Wed, Jul 21 - Sun, Aug 01
from (US$)$5,280

Solar Eclipse: Spain, Portugal, Morocco

  • Barcelona
  • Palma de Mallorca, Spain
  • Málaga, Spain
  • Seville (Cádiz), Spain
  • Tangier, Morocco
  • Funchal, Madeira, Portugal
  • Valencia, Spain
  • Barcelona
Insider cabins from
$6,270$9,374
per Cabin
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11 nights
Resilient Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$6,270$9,374
per Cabin
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Departing on:
2027
Wed, Jul 28 - Sun, Aug 08
from (US$)$6,270

Western Med: Barcelona to Rome

  • Barcelona
  • Cannes, France
  • Tuscany/Cinque Terre (La Spezia), Italy
  • Amalfi Coast (Salerno), Italy
  • Catania, Sicily, Italy
  • Valletta, Malta
  • Rome (Civitavecchia)
Insider cabins from
$3,672$5,394
per Cabin
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9 nights
Resilient Lady
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$3,672$5,394
per Cabin
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Departing on:
2027
Sun, Aug 08 - Tue, Aug 17
from (US$)$3,672

Italy, Spain & French Riviera

  • Barcelona
  • Provence (Marseille), France
  • Cannes, France
  • Ajaccio, Corsica, France
  • Rome (Civitavecchia), Italy
  • Amalfi Coast (Salerno), Italy
  • Catania, Sicily, Italy
  • Palma de Mallorca, Spain
  • Barcelona
Insider cabins from
$4,280$6,294
per Cabin
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10 nights
Resilient Lady
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+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$4,280$6,294
per Cabin
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Departing on:
2027
Thu, Sep 02 - Sun, Sep 12
from (US$)$4,280

Italy, Spain & French Riviera

  • Barcelona
  • Provence (Marseille), France
  • Cannes, France
  • Florence/Pisa (Livorno), Italy
  • Valencia, Spain
  • Palma de Mallorca, Spain
  • Barcelona
Insider cabins from
$2,786$4,022
per Cabin
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7 nights
Resilient Lady
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+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,786$4,022
per Cabin
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Departing on:
2027
Sun, Oct 10 - Sun, Oct 17
from (US$)$2,786

Adriatic, Albania and Mykonos Magic

  • Athens (Piraeus)
  • Dubrovnik, Croatia
  • Sarandë, Albania
  • Corfu, Greece
  • Mykonos, Greece
  • Athens (Piraeus)
Insider cabins from
$3,066$4,436
per Cabin
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7 nights
Scarlet Lady
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+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$3,066$4,436
per Cabin
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Departing on:
2027
Sun, Oct 17 - Sun, Oct 24
from (US$)$3,066

Med Coastal Medley: Athens to Barcelona

  • Athens (Piraeus)
  • Mykonos, Greece
  • Amalfi Coast (Salerno), Italy
  • Cannes, France
  • Barcelona
Insider cabins from
$2,786$4,034
per Cabin
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7 nights
Scarlet Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off a second Sailor
Insider cabins from
$2,786$4,034
per Cabin
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Departing on:
2027
Sun, Oct 24 - Sun, Oct 31
from (US$)$2,786
Average starting price per cabin (incl. taxes & fees)