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Explore 393 cruise vacations

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

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

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Showing 36 cruise vacations that match your search
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★
UP TO $700 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
$1,386$1,798
per Cabin
7 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,386$1,798
per Cabin
Departing on:
2025
Fri, Oct 31 - Fri, Nov 07
from (US$)$1,386
★
UP TO $700 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
7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,806$2,526
per Cabin
Departing on:
2025
Sat, Nov 01 - Sat, Nov 08
from (US$)$1,806Brilliant Lady's Inaugural Season
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EPIC SAVINGS ON ALL VOYAGES THROUGH 2027
70% off 2nd Sailor + up to $700* off
BOOK NOW

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 View cabins from
$1,308$1,832
per Cabin
6 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
$1,308$1,832
per Cabin
Departing on:
2025
Sun, Nov 02 - Sat, Nov 08
from (US$)$1,308

Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,490$2,080
per Cabin
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5 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,490$2,080
per Cabin
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Departing on:
2025Best Rate
Fri, Nov 07 - Wed, Nov 12
from (US$)$1,490
2025
Fri, Dec 05 - Wed, Dec 10
from (US$)$1,490
★
UP TO $700 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
$3,336$4,866
per Cabin
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12 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
$3,336$4,866
per Cabin
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Departing on:
2025
Sat, Nov 08 - Thu, Nov 20
from (US$)$3,336Brilliant Lady's Inaugural Season
★
UP TO $700 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
Insider cabins from
$1,386$1,972
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,386$1,972
per Cabin
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Departing on:
2025
Sat, Nov 08 - Sat, Nov 15
from (US$)$1,386

Western Caribbean & Bimini Beach Club

  • Miami, Florida
  • Costa Maya, Mexico
  • Roatán, Honduras
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,508$2,014
per Cabin
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6 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,508$2,014
per Cabin
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Departing on:
2025
Sun, Nov 09 - Sat, Nov 15
from (US$)$1,508

Fire & Sunset Soirées

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,350$1,852
per Cabin
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4 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,350$1,852
per Cabin
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Departing on:
2025Best Rate
Wed, Nov 12 - Sun, Nov 16
from (US$)$1,350
2025
Wed, Nov 26 - Sun, Nov 30
from (US$)$1,882
2025
Wed, Dec 10 - Sun, Dec 14
from (US$)$1,352
★
UP TO $700 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
$1,484$2,038
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,484$2,038
per Cabin
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Departing on:
2025
Sat, Nov 15 - Sat, Nov 22
from (US$)$1,484
★
UP TO $700 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
$2,872$4,266
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea Terrace cabins from
$2,872$4,266
per Cabin
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Departing on:
2025
Sat, Nov 15 - Sat, Nov 22
from (US$)$2,872

Riviera Maya

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,090$1,396
per Cabin
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5 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,090$1,396
per Cabin
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Departing on:
2025Best Rate
Sun, Nov 16 - Fri, Nov 21
from (US$)$1,090
2025
Sun, Dec 14 - Fri, Dec 19
from (US$)$1,190
★
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

Miami, Grand Turk (& back)

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
$1,890$2,708
per Cabin
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5 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea Terrace cabins from
$1,890$2,708
per Cabin
Loading
Departing on:
2025Best Rate
Sun, Nov 30 - Fri, Dec 05
from (US$)$1,890
2025
Fri, Nov 21 - Wed, Nov 26
from (US$)$2,108
2025
Fri, Dec 19 - Wed, Dec 24
from (US$)$2,412
★
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$1,880
per Cabin
Loading
Departing on:
2025Best Rate
Sat, Nov 22 - Sat, Nov 29
from (US$)$1,386
2025
Sat, Dec 06 - Sat, Dec 13
from (US$)$1,386
★
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
Loading
9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,962$2,800
per Cabin
Loading
Departing on:
2025
Fri, Nov 28 - Sun, Dec 07
from (US$)$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
★
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
Insider cabins from
$1,584$2,274
per Cabin
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8 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,584$2,274
per Cabin
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Departing on:
2025
Fri, Dec 05 - Sat, Dec 13
from (US$)$1,584
★
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
Loading
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
★
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
Sea View cabins from
$2,726$3,992
per Cabin
Loading
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
$2,726$3,992
per Cabin
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Departing on:
2025
Thu, Dec 18 - Fri, Dec 26
from (US$)$2,726Brilliant 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
Sea View cabins from
$2,374$3,408
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
$2,374$3,408
per Cabin
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Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from (US$)$2,374
★
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
★
UP TO $700 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
$4,758$7,134
per Cabin
Loading
9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$4,758$7,134
per Cabin
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Departing on:
2025
Fri, Dec 26 - Sun, Jan 04
from (US$)$4,758Brilliant Lady's Inaugural Season
★
UP TO $700 OFF

Resilient New Year's Ahoy!

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$4,194$6,198
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
$4,194$6,198
per Cabin
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Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from (US$)$4,194
★
UP TO $700 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
Insider cabins from
$3,604$5,406
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$3,604$5,406
per Cabin
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Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from (US$)$3,604

Scarlet New Year's Ahoy!

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$3,522$5,136
per Cabin
Loading
5 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
$3,522$5,136
per Cabin
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Departing on:
2025
Sun, Dec 28 - Fri, Jan 02
from (US$)$3,522
Average starting price per cabin (incl. taxes & fees)