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Explore 392 cruise vacations

Showing Loading cruise vacations: All Destinations, November 2025 - December 2025

Last chance: 70% off 2nd Sailor + Instant Savings

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Showing 21 cruise vacations that match your search
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★
UP TO $700 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
Insider 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
70% off second Sailor
Insider 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
★
UP TO $700 OFF

Cayman Coves & Jamaican Waterfalls

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,386$1,880
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,386$1,880
per Cabin
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Departing on:
2025Best Rate
Sat, Nov 22 - Sat, Nov 29
from (US$)$1,386
2025
Sat, Dec 06 - Sat, Dec 13
from (US$)$1,386
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EPIC SAVINGS ON ALL VOYAGES THROUGH 2027
70% off 2nd Sailor + up to $700* off
BOOK NOW
★
UP TO $700 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
$1,386$1,970
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,386$1,970
per Cabin
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Departing on:
2025
Sat, Nov 22 - Sat, Nov 29
from (US$)$1,386

Fire & Sunset Soirées

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$1,352$1,856
per Cabin
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4 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
$1,352$1,856
per Cabin
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Departing on:
2025Best Rate
Wed, Dec 10 - Sun, Dec 14
from (US$)$1,352
2025
Wed, Nov 26 - Sun, Nov 30
from (US$)$1,882
★
UP TO $700 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
Insider cabins from
$1,962$2,800
per Cabin
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9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,962$2,800
per Cabin
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Departing on:
2025
Fri, Nov 28 - Sun, Dec 07
from (US$)$1,962Brilliant Lady's Inaugural Season
★
UP TO $700 OFF

Eastern Caribbean & Bimini Beach Club

  • Miami, Florida
  • San Juan, Puerto Rico
  • Samaná, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,386$1,900
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,386$1,900
per Cabin
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Departing on:
2025
Sat, Nov 29 - Sat, Dec 06
from (US$)$1,386

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
$1,492$2,164
per Cabin
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6 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,492$2,164
per Cabin
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Departing on:
2025
Sat, Nov 29 - Fri, Dec 05
from (US$)$1,492

Miami, Grand Turk (& back)

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$1,590$2,246
per Cabin
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5 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
$1,590$2,246
per Cabin
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Departing on:
2025Best Rate
Sun, Nov 30 - Fri, Dec 05
from (US$)$1,590
2025
Fri, Dec 19 - Wed, Dec 24
from (US$)$2,016

Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$1,490$2,080
per Cabin
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5 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
$1,490$2,080
per Cabin
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Departing on:
2025
Fri, Dec 05 - Wed, Dec 10
from (US$)$1,490
★
UP TO $700 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
Sea View cabins from
$1,744$2,520
per Cabin
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8 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
$1,744$2,520
per Cabin
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Departing on:
2025
Fri, Dec 05 - Sat, Dec 13
from (US$)$1,744
★
UP TO $700 OFF

Aruban Sunsets & Calm Cayman Days

  • Miami, Florida
  • Oranjestad, Aruba
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
$2,530$3,648
per Cabin
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11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,530$3,648
per Cabin
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Departing on:
2025
Sun, Dec 07 - Thu, Dec 18
from (US$)$2,530Brilliant Lady's Inaugural Season
★
UP TO $700 OFF

Cayman Coves & Jamaican Waterfalls

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,464$1,998
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,464$1,998
per Cabin
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Departing on:
2025
Sat, Dec 13 - Sat, Dec 20
from (US$)$1,464
★
UP TO $700 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
$1,458$2,094
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,458$2,094
per Cabin
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Departing on:
2025
Sat, Dec 13 - Sat, Dec 20
from (US$)$1,458

Riviera Maya

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$1,390$1,858
per Cabin
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5 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
$1,390$1,858
per Cabin
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Departing on:
2025
Sun, Dec 14 - Fri, Dec 19
from (US$)$1,390
★
UP TO $700 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
$2,206$3,192
per Cabin
Loading
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,206$3,192
per Cabin
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Departing on:
2025
Thu, Dec 18 - Fri, Dec 26
from (US$)$2,206Brilliant Lady's Inaugural Season
★
UP TO $700 OFF

Resilient Caribbean Holidays

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,072$2,942
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,072$2,942
per Cabin
Loading
Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from (US$)$2,072
★
UP TO $700 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
Insider cabins from
$2,084$3,046
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,084$3,046
per Cabin
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Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from (US$)$2,084

Scarlet Caribbean Holidays

  • Miami, Florida
  • Nassau, Bahamas
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
$2,040$2,930
per Cabin
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4 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea Terrace cabins from
$2,040$2,930
per Cabin
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Departing on:
2025
Wed, Dec 24 - Sun, Dec 28
from (US$)$2,040
Average starting price per cabin (incl. taxes & fees)