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Explore 415 cruise vacations

Showing Loading cruise vacations: Caribbean, September 2025 - December 2026
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Showing 183 cruise vacations that match your search
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Fire & Sunset Soirées

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,032$1,368
per Cabin
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4 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 second Sailor
Insider cabins from
$1,032$1,368
per Cabin
Loading
Departing on:
2025Best Rate
Wed, Sep 17 - Sun, Sep 21
from (US$)$1,032
2025
Wed, Nov 12 - Sun, Nov 16
from (US$)$1,592
2025
Wed, Nov 26 - Sun, Nov 30
from (US$)$1,592
* Port changes in place on select sailings — see full cruise details

Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,390$1,888
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.
Learn more
70% off second Sailor
Insider cabins from
$1,390$1,888
per Cabin
Loading
Departing on:
2026Best Rate
Mon, Sep 14 - Sat, Sep 19
from (US$)$1,390
2025
Fri, Sep 26 - Wed, Oct 01
from (US$)$2,500
2025
Fri, Nov 07 - Wed, Nov 12
from (US$)$1,790
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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 second Sailor
Insider cabins from
$1,290$1,714
per Cabin
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Departing on:
2025Best Rate
Sun, Oct 05 - Fri, Oct 10
from (US$)$1,290
2026
Mon, Jun 22 - Sat, Jun 27
from (US$)$1,890
2026
Sat, Nov 28 - Thu, Dec 03
from (US$)$1,590

True Crime Voyage

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,290$1,774
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 second Sailor
Insider cabins from
$1,290$1,774
per Cabin
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Departing on:
2025
Fri, Oct 10 - Wed, Oct 15
from (US$)$1,290

Scarlet's Haunted Halloween Soirée

  • Barcelona
  • Palma de Mallorca, Spain
  • Casablanca, Morocco
  • Funchal, Madeira, Portugal
  • Santa Cruz de Tenerife, Spain
  • Miami, Florida
Sea Terrace cabins from
$3,570$5,328
per Cabin
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15 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 second Sailor
Sea Terrace cabins from
$3,570$5,328
per Cabin
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Departing on:
2025
Thu, Oct 16 - Fri, Oct 31
from (US$)$3,570
★
UP TO $600 OFF

Brilliant Lady Miami MerMaiden

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,384$3,436
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 second Sailor
Insider cabins from
$2,384$3,436
per Cabin
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Departing on:
2025
Fri, Oct 17 - Sat, Oct 25
from (US$)$2,384Brilliant Lady's Inaugural Season

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
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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 second Sailor
Insider cabins from
$1,290$1,704
per Cabin
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Departing on:
2025
Sun, Oct 19 - Fri, Oct 24
from (US$)$1,290

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 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

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
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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 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
★
UP TO $600 OFF

Scarlet's Haunted Halloween Soirée

  • Miami, Florida
  • Roatán, Honduras
  • Costa Maya, Mexico
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,526$2,014
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 second Sailor
Insider cabins from
$1,526$2,014
per Cabin
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Departing on:
2025
Fri, Oct 31 - Fri, Nov 07
from (US$)$1,526
★
UP TO $600 OFF

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 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

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
$1,308$1,832
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.
Learn more
70% off second Sailor
Insider cabins from
$1,308$1,832
per Cabin
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Departing on:
2025
Sun, Nov 02 - Sat, Nov 08
from (US$)$1,308
★
UP TO $600 OFF

Colorful Curaçao to the Charming Caymans

  • Miami, Florida
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Sea View cabins from
$3,338$4,868
per Cabin
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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 second Sailor
Sea View cabins from
$3,338$4,868
per Cabin
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Departing on:
2025
Sat, Nov 08 - Thu, Nov 20
from (US$)$3,338Brilliant Lady's Inaugural Season
★
UP TO $600 OFF

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
Sea View cabins from
$2,786$4,126
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 second Sailor
Sea View cabins from
$2,786$4,126
per Cabin
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Departing on:
2025Best Rate
Sat, Nov 08 - Sat, Nov 15
from (US$)$2,786
2026
Sat, Mar 21 - Sat, Mar 28
from (US$)$3,360

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.
Learn more
70% off 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
★
UP TO $600 OFF

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
$1,666$2,318
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 second Sailor
Insider cabins from
$1,666$2,318
per Cabin
Loading
Departing on:
2025Best Rate
Sat, Nov 15 - Sat, Nov 22
from (US$)$1,666
2026
Sat, Mar 28 - Sat, Apr 04
from (US$)$2,506
2026
Sat, Apr 18 - Sat, Apr 25
from (US$)$2,506
★
UP TO $600 OFF

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
Sea View cabins from
$1,806$2,628
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 second Sailor
Sea View cabins from
$1,806$2,628
per Cabin
Loading
Departing on:
2025Best Rate
Sat, Nov 15 - Sat, Nov 22
from (US$)$1,806
2026
Sat, Feb 28 - Sat, Mar 07
from (US$)$2,226
2026
Sat, Nov 07 - Sat, Nov 14
from (US$)$1,806

Riviera Maya

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,390$1,858
per Cabin
Loading
5 nights
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 second Sailor
Insider cabins from
$1,390$1,858
per Cabin
Loading
Departing on:
2025Best Rate
Sun, Nov 16 - Fri, Nov 21
from (US$)$1,390
2025
Sun, Dec 14 - Fri, Dec 19
from (US$)$1,390
2026
Sun, Jan 11 - Fri, Jan 16
from (US$)$1,390
★
UP TO $600 OFF

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
Sea View cabins from
$2,064$2,972
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 second Sailor
Sea View cabins from
$2,064$2,972
per Cabin
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Departing on:
2025
Thu, Nov 20 - Fri, Nov 28
from (US$)$2,064Brilliant 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
$1,490$2,022
per Cabin
Loading
5 nights
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 second Sailor
Insider cabins from
$1,490$2,022
per Cabin
Loading
Departing on:
2026Best Rate
Sat, Aug 22 - Thu, Aug 27
from (US$)$1,490
2025
Fri, Nov 21 - Wed, Nov 26
from (US$)$1,790
2025
Sun, Nov 30 - Fri, Dec 05
from (US$)$1,790
★
UP TO $600 OFF

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 second Sailor
Sea View cabins from
$1,806$2,526
per Cabin
Loading
Departing on:
2025Best Rate
Sat, Nov 22 - Sat, Nov 29
from (US$)$1,806
2025
Sat, Dec 06 - Sat, Dec 13
from (US$)$1,806
2026
Sat, Jan 24 - Sat, Jan 31
from (US$)$2,240
★
UP TO $600 OFF

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
$1,666$2,400
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 second Sailor
Insider cabins from
$1,666$2,400
per Cabin
Loading
Departing on:
2025
Sat, Nov 22 - Sat, Nov 29
from (US$)$1,666
★
UP TO $600 OFF

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
Sea View cabins from
$2,504$3,632
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 second Sailor
Sea View cabins from
$2,504$3,632
per Cabin
Loading
Departing on:
2025Best Rate
Fri, Nov 28 - Sun, Dec 07
from (US$)$2,504Brilliant Lady's Inaugural Season
2026
Fri, Feb 20 - Sun, Mar 01
from (US$)$2,864Brilliant Lady's Inaugural Season

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
Sea Terrace cabins from
$1,788$2,620
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.
Learn more
70% off second Sailor
Sea Terrace cabins from
$1,788$2,620
per Cabin
Loading
Departing on:
2025
Sat, Nov 29 - Fri, Dec 05
from (US$)$1,788
★
UP TO $600 OFF

San Juan, Samaná & Bimini

  • Miami, Florida
  • San Juan, Puerto Rico
  • Samaná, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,666$2,330
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 second Sailor
Insider cabins from
$1,666$2,330
per Cabin
Loading
Departing on:
2025Best Rate
Sat, Nov 29 - Sat, Dec 06
from (US$)$1,666
2026
Sat, Jan 17 - Sat, Jan 24
from (US$)$2,088
★
UP TO $600 OFF

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
$1,904$2,766
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.
Learn more
70% off second Sailor
Insider cabins from
$1,904$2,766
per Cabin
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Departing on:
2025
Fri, Dec 05 - Sat, Dec 13
from (US$)$1,904
★
UP TO $600 OFF

Aruban Sunsets & Calm Cayman Days

  • Miami, Florida
  • Oranjestad, Aruba
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
$2,620$3,786
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.
Learn more
70% off second Sailor
Insider cabins from
$2,620$3,786
per Cabin
Loading
Departing on:
2025Best Rate
Sun, Dec 07 - Thu, Dec 18
from (US$)$2,620Brilliant Lady's Inaugural Season
2026
Sun, Mar 01 - Thu, Mar 12
from (US$)$3,192Brilliant Lady's Inaugural Season
★
UP TO $600 OFF

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 second Sailor
Sea View cabins from
$1,806$2,526
per Cabin
Loading
Departing on:
2025Best Rate
Sat, Dec 13 - Sat, Dec 20
from (US$)$1,806
2026
Sat, Feb 07 - Sat, Feb 14
from (US$)$2,366
★
UP TO $600 OFF

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
$1,666$2,416
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 second Sailor
Insider cabins from
$1,666$2,416
per Cabin
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Departing on:
2025
Sat, Dec 13 - Sat, Dec 20
from (US$)$1,666
★
UP TO $600 OFF

Brilliant Caribbean Holidays

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Samaná, Dominican Republic
  • Miami, Florida
Insider cabins from
$2,640$3,862
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.
Learn more
70% off second Sailor
Insider cabins from
$2,640$3,862
per Cabin
Loading
Departing on:
2025
Thu, Dec 18 - Fri, Dec 26
from (US$)$2,640Brilliant Lady's Inaugural Season
★
UP TO $600 OFF

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
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 second Sailor
Sea View cabins from
$2,506$3,612
per Cabin
Loading
Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from (US$)$2,506
★
UP TO $600 OFF

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
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off 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
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Sea View cabins from
$1,592$2,242
per Cabin
Loading
Departing on:
2025Best Rate
Wed, Dec 24 - Sun, Dec 28
from (US$)$1,592
2026
Mon, Dec 21 - Sat, Dec 26
from (US$)$1,890
* Port changes in place on select sailings — see full cruise details
★
UP TO $600 OFF

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
$4,304$6,434
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 second Sailor
Insider cabins from
$4,304$6,434
per Cabin
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Departing on:
2025
Fri, Dec 26 - Sun, Jan 04
from (US$)$4,304Brilliant Lady's Inaugural Season
★
UP TO $600 OFF

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.
Learn more
70% off 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
★
UP TO $600 OFF

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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70% off 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 amount depends on cabin availability and selection at the time of purchase.
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70% off 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
★
UP TO $600 OFF

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
$2,366$3,496
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 second Sailor
Sea View cabins from
$2,366$3,496
per Cabin
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Departing on:
2026
Sat, Jan 03 - Sat, Jan 10
from (US$)$2,366
★
UP TO $600 OFF

Cozumel, Grand Cayman & Bimini

  • Miami, Florida
  • George Town, Grand Cayman
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$2,226$3,116
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 second Sailor
Sea View cabins from
$2,226$3,116
per Cabin
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Departing on:
2026
Sat, Jan 03 - Sat, Jan 10
from (US$)$2,226
★
UP TO $600 OFF

Aruba, Bonaire, Colombia, Jamaica & More

  • Miami, Florida
  • Oranjestad, Aruba
  • Kralendijk, Bonaire
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
$2,840$4,116
per Cabin
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11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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70% off second Sailor
Insider cabins from
$2,840$4,116
per Cabin
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Departing on:
2026
Sun, Jan 04 - Thu, Jan 15
from (US$)$2,840Brilliant Lady's Inaugural Season
★
UP TO $600 OFF

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
BOOK NOW
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off second Sailor
Insider cabins from
$1,946$2,746
per Cabin
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Departing on:
2026Best Rate
Sun, Dec 13 - Sun, Dec 20
from (US$)$1,946
2026
Sat, Jan 10 - Sat, Jan 17
from (US$)$2,088
2026
Sat, Mar 07 - Sat, Mar 14
from (US$)$2,590
★
UP TO $600 OFF

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
$2,086$3,078
per Cabin
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7 nights
Valiant Lady
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70% off second Sailor
Sea View cabins from
$2,086$3,078
per Cabin
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Departing on:
2026
Sat, Jan 10 - Sat, Jan 17
from (US$)$2,086
★
UP TO $600 OFF

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
$2,086$3,066
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 second Sailor
Sea View cabins from
$2,086$3,066
per Cabin
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Departing on:
2026
Sat, Jan 17 - Sat, Jan 24
from (US$)$2,086
★
UP TO $600 OFF

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
$2,088$3,062
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 second Sailor
Sea View cabins from
$2,088$3,062
per Cabin
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Departing on:
2026
Sat, Jan 24 - Sat, Jan 31
from (US$)$2,088

Grand Turk, Puerto Plata & Bimini

  • Miami, Florida
  • The Beach Club at Bimini, Bahamas
  • Puerto Plata, Dominican Republic
  • Grand Turk, Turks and Caicos
  • Miami, Florida
Sea View cabins from
$2,268$3,264
per Cabin
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6 nights
Brilliant Lady
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70% off second Sailor
Sea View cabins from
$2,268$3,264
per Cabin
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Departing on:
2026
Mon, Jan 26 - Sun, Feb 01
from (US$)$2,268
★
UP TO $600 OFF

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
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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 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
★
UP TO $600 OFF

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
$1,948$2,766
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 second Sailor
Sea View cabins from
$1,948$2,766
per Cabin
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Departing on:
2026Best Rate
Sat, Jan 31 - Sat, Feb 07
from (US$)$1,948
2026
Sat, Feb 28 - Sat, Mar 07
from (US$)$2,086
2026
Sun, Dec 06 - Sun, Dec 13
from (US$)$2,086
★
UP TO $600 OFF

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
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11 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 second Sailor
Sea View cabins from
$3,278$4,788
per Cabin
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Departing on:
2026
Sun, Feb 01 - Thu, Feb 12
from (US$)$3,278Brilliant Lady's Inaugural Season
★
UP TO $600 OFF

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 Terrace cabins from
$2,646$3,908
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 second Sailor
Sea Terrace cabins from
$2,646$3,908
per Cabin
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Departing on:
2026
Sat, Feb 07 - Sat, Feb 14
from (US$)$2,646
★
UP TO $600 OFF

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
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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 second Sailor
Insider cabins from
$2,544$3,718
per Cabin
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Departing on:
2026
Thu, Feb 12 - Fri, Feb 20
from (US$)$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
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off second Sailor
Sea View cabins from
$1,890$2,702
per Cabin
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Departing on:
2026
Fri, Feb 13 - Wed, Feb 18
from (US$)$1,890
★
UP TO $600 OFF

Resilient Valentine's Voyage

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$2,506$3,608
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 second Sailor
Sea View cabins from
$2,506$3,608
per Cabin
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Departing on:
2026
Sat, Feb 14 - Sat, Feb 21
from (US$)$2,506

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
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off second Sailor
Sea View cabins from
$2,226$3,284
per Cabin
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Departing on:
2026
Sat, Feb 14 - Sat, Feb 21
from (US$)$2,226
★
UP TO $600 OFF

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
$2,940$4,374
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 second Sailor
Sea View cabins from
$2,940$4,374
per Cabin
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Departing on:
2026
Sat, Feb 21 - Sat, Feb 28
from (US$)$2,940
★
UP TO $600 OFF

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 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
★
UP TO $600 OFF

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
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off 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
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off 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
★
UP TO $600 OFF

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
$1,806$2,628
per Cabin
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7 nights
Valiant Lady
BOOK NOW
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off second Sailor
Insider cabins from
$1,806$2,628
per Cabin
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Departing on:
2026Best Rate
Sat, Dec 05 - Sat, Dec 12
from (US$)$1,806
2026
Sat, Mar 14 - Sat, Mar 21
from (US$)$3,066
★
UP TO $600 OFF

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
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off 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

Cayman Isles & Bimini Beach Miles

  • Miami, Florida
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,490$2,048
per Cabin
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5 nights
Resilient Lady & 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 second Sailor
Insider cabins from
$1,490$2,048
per Cabin
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Departing on:
2026Best Rate
Mon, Nov 09 - Sat, Nov 14
from (US$)$1,490
2026
Mon, Jun 08 - Sat, Jun 13
from (US$)$1,890
2026
Sat, Jun 13 - Thu, Jun 18
from (US$)$2,190

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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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off 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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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off 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

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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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off 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
$1,946$2,844
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 second Sailor
Insider cabins from
$1,946$2,844
per Cabin
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Departing on:
2026
Sat, Oct 31 - Sat, Nov 07
from (US$)$1,946

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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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off 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
  • St. John's, Antigua
  • Castries, St. Lucia
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
Insider cabins from
$1,550$2,182
per Cabin
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6 nights
Valiant Lady
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70% off second Sailor
Insider cabins from
$1,550$2,182
per Cabin
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Departing on:
2026
Sat, Nov 14 - Fri, Nov 20
from (US$)$1,550

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
Sea View cabins from
$3,180$4,622
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 second Sailor
Sea View cabins from
$3,180$4,622
per Cabin
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Departing on:
2026
Sun, Nov 15 - Wed, Nov 25
from (US$)$3,180

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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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off 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
$2,384$3,488
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 second Sailor
Insider cabins from
$2,384$3,488
per Cabin
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Departing on:
2026
Fri, Nov 20 - Sat, Nov 28
from (US$)$2,384

Jamaican Waves & Bimini Breeze

  • Miami, Florida
  • Ocho Rios, Jamaica
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,790$2,484
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 second Sailor
Insider cabins from
$1,790$2,484
per Cabin
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Departing on:
2026
Mon, Nov 23 - Sat, Nov 28
from (US$)$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
$1,948$2,778
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 second Sailor
Insider cabins from
$1,948$2,778
per Cabin
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Departing on:
2026
Sat, Nov 28 - Sat, Dec 05
from (US$)$1,948

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
Sea View cabins from
$3,180$4,606
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 second Sailor
Sea View cabins from
$3,180$4,606
per Cabin
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Departing on:
2026
Mon, Nov 30 - Thu, Dec 10
from (US$)$3,180

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 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 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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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off 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 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
$3,488$5,198
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 second Sailor
Insider cabins from
$3,488$5,198
per Cabin
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Departing on:
2026
Sat, Dec 26 - Sat, Jan 02
from (US$)$3,488

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+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off 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+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off 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
Average starting price per cabin (incl. taxes & fees)