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Explore 390 cruise vacations

Showing Loading cruise vacations: All Destinations, October 2025 - December 2025
Showing 34 cruise vacations that match your search
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Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,490$2,220
per Cabin
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5 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Insider cabins from
$1,490$2,220
per Cabin
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Departing on:
2025Best Rate
Fri, Nov 07 - Wed, Nov 12
from (US$)$1,490
2025
Fri, Dec 05 - Wed, Dec 10
from (US$)$1,490

Colorful Curaçao to the Charming Caymans

  • Miami, Florida
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
$2,856$4,432
per Cabin
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12 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Insider cabins from
$2,856$4,432
per Cabin
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Departing on:
2025
Sat, Nov 08 - Thu, Nov 20
from (US$)$2,856Brilliant Lady's Inaugural Season

Saint (Isles) & Seas of the Caribbean

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Bridgetown, Barbados
  • Castries, St. Lucia
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
$1,386$2,112
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,386$2,112
per Cabin
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Departing on:
2025
Sat, Nov 08 - Sat, Nov 15
from (US$)$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
$1,456$2,046
per Cabin
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6 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,456$2,046
per Cabin
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Departing on:
2025
Sun, Nov 09 - Sat, Nov 15
from (US$)$1,456

Fire & Sunset Soirées

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$1,352$1,976
per Cabin
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4 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Sea View cabins from
$1,352$1,976
per Cabin
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Departing on:
2025Best Rate
Wed, Dec 10 - Sun, Dec 14
from (US$)$1,352
2025
Wed, Nov 12 - Sun, Nov 16
from (US$)$1,432
2025
Wed, Nov 26 - Sun, Nov 30
from (US$)$2,454

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
$1,386$2,008
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,386$2,008
per Cabin
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Departing on:
2025
Sat, Nov 15 - Sat, Nov 22
from (US$)$1,386

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
$2,876$4,606
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea Terrace cabins from
$2,876$4,606
per Cabin
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Departing on:
2025
Sat, Nov 15 - Sat, Nov 22
from (US$)$2,876

Riviera Maya

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,090$1,470
per Cabin
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5 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Insider cabins from
$1,090$1,470
per Cabin
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Departing on:
2025Best Rate
Sun, Nov 16 - Fri, Nov 21
from (US$)$1,090
2025
Sun, Dec 14 - Fri, Dec 19
from (US$)$1,390

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
$2,224$3,456
per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea View cabins from
$2,224$3,456
per Cabin
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Departing on:
2025
Thu, Nov 20 - Fri, Nov 28
from (US$)$2,224Brilliant Lady's Inaugural Season

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$2,402
per Cabin
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5 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Sea View cabins from
$1,590$2,402
per Cabin
Loading
Departing on:
2025Best Rate
Sun, Nov 30 - Fri, Dec 05
from (US$)$1,590
2025
Fri, Nov 21 - Wed, Nov 26
from (US$)$2,110
2025
Fri, Dec 19 - Wed, Dec 24
from (US$)$1,890

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$1,998
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,386$1,998
per Cabin
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Departing on:
2025Best Rate
Sat, Nov 22 - Sat, Nov 29
from (US$)$1,386
2025
Sat, Dec 06 - Sat, Dec 13
from (US$)$1,386

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$2,110
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,386$2,110
per Cabin
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Departing on:
2025
Sat, Nov 22 - Sat, Nov 29
from (US$)$1,386

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$3,000
per Cabin
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9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,962$3,000
per Cabin
Loading
Departing on:
2025
Fri, Nov 28 - Sun, Dec 07
from (US$)$1,962Brilliant Lady's Inaugural Season

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$2,022
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,386$2,022
per Cabin
Loading
Departing on:
2025
Sat, Nov 29 - Sat, Dec 06
from (US$)$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
RockStar Quarters suites from
$4,440
per Cabin
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6 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
RockStar Quarters suites from
$4,440
per Cabin
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Departing on:
2025
Sat, Nov 29 - Fri, Dec 05
from (US$)$4,440
Only suites remaining

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$2,706
per Cabin
Loading
8 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea View cabins from
$1,744$2,706
per Cabin
Loading
Departing on:
2025
Fri, Dec 05 - Sat, Dec 13
from (US$)$1,744

Aruban Sunsets & Calm Cayman Days

  • Miami, Florida
  • Oranjestad, Aruba
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
$2,532$3,918
per Cabin
Loading
11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Insider cabins from
$2,532$3,918
per Cabin
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Departing on:
2025
Sun, Dec 07 - Thu, Dec 18
from (US$)$2,532Brilliant Lady's Inaugural Season

Cayman Coves & Jamaican Waterfalls

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,386$1,998
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,386$1,998
per Cabin
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Departing on:
2025
Sat, Dec 13 - Sat, Dec 20
from (US$)$1,386

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
$1,412$2,170
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,412$2,170
per Cabin
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Departing on:
2025
Sat, Dec 13 - Sat, Dec 20
from (US$)$1,412

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
$2,064$3,192
per Cabin
Loading
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$2,064$3,192
per Cabin
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Departing on:
2025
Thu, Dec 18 - Fri, Dec 26
from (US$)$2,064Brilliant Lady's Inaugural Season

Resilient Caribbean Holidays

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$2,226$3,408
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea View cabins from
$2,226$3,408
per Cabin
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Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from (US$)$2,226

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
$1,946$3,046
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,946$3,046
per Cabin
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Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from (US$)$1,946

Scarlet Caribbean Holidays

  • Miami, Florida
  • Nassau, Bahamas
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
$1,912$2,930
per Cabin
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4 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Sea Terrace cabins from
$1,912$2,930
per Cabin
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Departing on:
2025
Wed, Dec 24 - Sun, Dec 28
from (US$)$1,912

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
$3,942$6,340
per Cabin
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9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$3,942$6,340
per Cabin
Loading
Departing on:
2025
Fri, Dec 26 - Sun, Jan 04
from (US$)$3,942Brilliant Lady's Inaugural Season

Resilient New Year's Ahoy!

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$3,616$5,712
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$3,616$5,712
per Cabin
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Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from (US$)$3,616

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
$3,346$5,406
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$3,346$5,406
per Cabin
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Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from (US$)$3,346

Scarlet New Year's Ahoy!

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$3,290$5,136
per Cabin
Loading
5 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Sea View cabins from
$3,290$5,136
per Cabin
Loading
Departing on:
2025
Sun, Dec 28 - Fri, Jan 02
from (US$)$3,290
Average starting price per cabin (incl. taxes & fees)