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Explore 414 cruise vacations

Showing Loading cruise vacations: All Destinations, September 2025 - November 2025
Sea Terrace
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Winter Caribbean sailings from $109 pp/pn
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from Miami or San Juan
Showing 34 cruise vacations that match your search
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Istanbul, Santorini & More

  • Athens (Piraeus)
  • Istanbul, Turkey
  • Ephesus (Kuşadasi), Turkey
  • Mykonos, Greece
  • Rhodes, Greece
  • Santorini, Greece
  • Chania (Souda Bay), Crete, Greece
  • Athens (Piraeus)
Sea Terrace cabins from
$5,610$8,202
per Cabin
11 nights
Resilient Lady
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70% off second Sailor
Sea Terrace cabins from
$5,610$8,202
per Cabin
Departing on:
2025
Sun, Sep 21 - Thu, Oct 02
from (US$)$5,610

Riviera Maya

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
$1,290
per Cabin
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5 nights
Valiant Lady & Scarlet Lady
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70% off second Sailor
Sea Terrace cabins from
$1,290
per Cabin
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Departing on:
2025Best Rate
Sun, Nov 16 - Fri, Nov 21
from (US$)$1,290
2025
Sun, Sep 21 - Fri, Sep 26
from (US$)$2,400
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EPIC SAVINGS ON ALL VOYAGES THROUGH 2027
70% off 2nd Sailor + up to $600* off
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Starry Nights in Greece & Croatia

  • Athens (Piraeus)
  • Santorini, Greece
  • Bodrum, Turkey
  • Mykonos, Greece
  • Dubrovnik, Croatia
  • Kotor, Montenegro
  • Corfu, Greece
  • Athens (Piraeus)
Sea Terrace cabins from
$5,200$7,626
per Cabin
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10 nights
Resilient Lady
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70% off second Sailor
Sea Terrace cabins from
$5,200$7,626
per Cabin
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Departing on:
2025
Thu, Oct 02 - Sun, Oct 12
from (US$)$5,200

Fall Leaves to Miami Scenes

  • Québec City, Québec
  • Halifax, Nova Scotia
  • Saint John, New Brunswick
  • Eastport, Maine
  • Boston, Massachusetts
  • Charleston, South Carolina
  • Miami, Florida
Sea Terrace cabins from
$4,940$7,286
per Cabin
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13 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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70% off second Sailor
Sea Terrace cabins from
$4,940$7,286
per Cabin
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Departing on:
2025
Fri, Oct 03 - Thu, Oct 16
from (US$)$4,940Brilliant Lady's Inaugural Season

Mayan Sol

  • Miami, Florida
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
$1,692$2,330
per Cabin
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5 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
$1,692$2,330
per Cabin
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Departing on:
2025
Sun, Oct 05 - Fri, Oct 10
from (US$)$1,692

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 Terrace cabins from
$4,500$6,724
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 second Sailor
Sea Terrace cabins from
$4,500$6,724
per Cabin
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Departing on:
2025
Tue, Oct 07 - Thu, Oct 16
from (US$)$4,500

True Crime Voyage

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
$1,790$2,542
per Cabin
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5 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
$1,790$2,542
per Cabin
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Departing on:
2025
Fri, Oct 10 - Wed, Oct 15
from (US$)$1,790

Greek Island Glow

  • Athens (Piraeus)
  • Santorini, Greece
  • Rhodes, Greece
  • Bodrum, Turkey
  • Mykonos, Greece
  • Athens (Piraeus)
Sea Terrace cabins from
$4,550$6,674
per Cabin
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7 nights
Resilient Lady
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70% off second Sailor
Sea Terrace cabins from
$4,550$6,674
per Cabin
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Departing on:
2025
Sun, Oct 12 - Sun, Oct 19
from (US$)$4,550

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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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
Sea Terrace cabins from
$3,024$4,420
per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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
Sea Terrace cabins from
$3,024$4,420
per Cabin
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Departing on:
2025
Fri, Oct 17 - Sat, Oct 25
from (US$)$3,024Brilliant 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
$3,206$4,668
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 Terrace cabins from
$3,206$4,668
per Cabin
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Departing on:
2025
Sun, Oct 19 - Sun, Oct 26
from (US$)$3,206

Riviera Maya: Halloween Edition

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
$1,690$2,320
per Cabin
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5 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
$1,690$2,320
per Cabin
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Departing on:
2025
Sun, Oct 19 - Fri, Oct 24
from (US$)$1,690

Dominican Daze: Halloween Edition

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
$1,792$2,542
per Cabin
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5 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
$1,792$2,542
per Cabin
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Departing on:
2025
Fri, Oct 24 - Wed, Oct 29
from (US$)$1,792

Valiant's Haunted Halloween Soirée

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
$1,752$2,472
per Cabin
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4 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
Sea Terrace cabins from
$1,752$2,472
per Cabin
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Departing on:
2025
Wed, Oct 29 - Sun, Nov 02
from (US$)$1,752
★
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
Sea Terrace cabins from
$1,794
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 second Sailor
Sea Terrace cabins from
$1,794
per Cabin
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Departing on:
2025
Fri, Oct 31 - Fri, Nov 07
from (US$)$1,794
★
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
Sea Terrace cabins from
$2,508$3,604
per Cabin
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7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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
Sea Terrace cabins from
$2,508$3,604
per Cabin
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Departing on:
2025
Sat, Nov 01 - Sat, Nov 08
from (US$)$2,508Brilliant 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
Sea Terrace cabins from
$1,544
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 second Sailor
Sea Terrace cabins from
$1,544
per Cabin
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Departing on:
2025
Sun, Nov 02 - Sat, Nov 08
from (US$)$1,544

Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
$2,190$3,156
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 Terrace cabins from
$2,190$3,156
per Cabin
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Departing on:
2025
Fri, Nov 07 - Wed, Nov 12
from (US$)$2,190
★
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 Terrace cabins from
$3,084
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.
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70% off second Sailor
Sea Terrace cabins from
$3,084
per Cabin
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Departing on:
2025
Sat, Nov 08 - Thu, Nov 20
from (US$)$3,084Brilliant 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 Terrace cabins from
$3,068$4,558
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
$3,068$4,558
per Cabin
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Departing on:
2025
Sat, Nov 08 - Sat, Nov 15
from (US$)$3,068

Western Caribbean Charm

  • Miami, Florida
  • Costa Maya, Mexico
  • Roatán, Honduras
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
$2,700$3,848
per Cabin
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6 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
Sea Terrace cabins from
$2,700$3,848
per Cabin
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Departing on:
2025
Sun, Nov 09 - Sat, Nov 15
from (US$)$2,700

Fire & Sunset Soirées

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
$1,832$2,594
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.
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70% off second Sailor
Sea Terrace cabins from
$1,832$2,594
per Cabin
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Departing on:
2025Best Rate
Wed, Nov 12 - Sun, Nov 16
from (US$)$1,832
2025
Wed, Nov 26 - Sun, Nov 30
from (US$)$1,832
★
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
Sea Terrace cabins from
$1,796
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 second Sailor
Sea Terrace cabins from
$1,796
per Cabin
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Departing on:
2025
Sat, Nov 15 - Sat, Nov 22
from (US$)$1,796
★
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 Terrace cabins from
$1,802
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
$1,802
per Cabin
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Departing on:
2025
Sat, Nov 15 - Sat, Nov 22
from (US$)$1,802
★
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 Terrace cabins from
$3,442$5,090
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
Sea Terrace cabins from
$3,442$5,090
per Cabin
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Departing on:
2025
Thu, Nov 20 - Fri, Nov 28
from (US$)$3,442Brilliant Lady's Inaugural Season

Miami, Grand Turk (& back)

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
$2,090$3,016
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 second Sailor
Sea Terrace cabins from
$2,090$3,016
per Cabin
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Departing on:
2025Best Rate
Sun, Nov 30 - Fri, Dec 05
from (US$)$2,090
2025
Fri, Nov 21 - Wed, Nov 26
from (US$)$2,190
★
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 Terrace cabins from
$2,086$2,956
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 second Sailor
Sea Terrace cabins from
$2,086$2,956
per Cabin
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Departing on:
2025
Sat, Nov 22 - Sat, Nov 29
from (US$)$2,086
★
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
Sea Terrace cabins from
$1,798
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
$1,798
per Cabin
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Departing on:
2025
Sat, Nov 22 - Sat, Nov 29
from (US$)$1,798
★
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 Terrace cabins from
$2,312
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 second Sailor
Sea Terrace cabins from
$2,312
per Cabin
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Departing on:
2025
Fri, Nov 28 - Sun, Dec 07
from (US$)$2,312Brilliant 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
$1,538
per Cabin
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6 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
Sea Terrace cabins from
$1,538
per Cabin
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Departing on:
2025
Sat, Nov 29 - Fri, Dec 05
from (US$)$1,538
★
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
Sea Terrace cabins from
$1,802
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 second Sailor
Sea Terrace cabins from
$1,802
per Cabin
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Departing on:
2025
Sat, Nov 29 - Sat, Dec 06
from (US$)$1,802
Average starting price per cabin (incl. taxes & fees)