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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
80% off second Sailor
Insider cabins from
$1,490$2,220
per Cabin
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Departing on:

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
80% off second Sailor
Insider cabins from
$2,856$4,432
per Cabin
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Departing on:

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
80% off second Sailor
Insider cabins from
$1,386$2,112
per Cabin
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Western Caribbean & Bimini Beach Club
- Miami, Florida
- Costa Maya, Mexico
- Roatán, Honduras
- The Beach Club at Bimini, Bahamas
- Miami, Florida
80% off second Sailor
Insider cabins from
$1,456$2,046
per Cabin
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Departing on:

Fire & Sunset Soirées
- Miami, Florida
- Key West, Florida
- The Beach Club at Bimini, Bahamas
- Miami, Florida
80% off second Sailor
Sea View cabins from
$1,352$1,976
per Cabin
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San Juan Sunrises & Dominican Dreams
- Miami, Florida
- San Juan, Puerto Rico
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
80% off second Sailor
Insider cabins from
$1,386$2,008
per Cabin
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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
80% off second Sailor
Sea Terrace cabins from
$2,876$4,606
per Cabin
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Riviera Maya
- Miami, Florida
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
80% off second Sailor
Insider cabins from
$1,090$1,470
per Cabin
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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
80% off second Sailor
Sea View cabins from
$2,224$3,456
per Cabin
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Miami, Grand Turk (& back)
- Miami, Florida
- Grand Turk, Turks and Caicos
- The Beach Club at Bimini, Bahamas
- Miami, Florida
80% off second Sailor
Sea View cabins from
$1,590$2,402
per Cabin
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Cayman Coves & Jamaican Waterfalls
- Miami, Florida
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- The Beach Club at Bimini, Bahamas
- Miami, Florida
80% off second Sailor
Insider cabins from
$1,386$1,998
per Cabin
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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
80% off second Sailor
Insider cabins from
$1,386$2,110
per Cabin
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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
80% off second Sailor
Insider cabins from
$1,962$3,000
per Cabin
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Eastern Caribbean & Bimini Beach Club
- Miami, Florida
- San Juan, Puerto Rico
- Samaná, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
80% off second Sailor
Insider cabins from
$1,386$2,022
per Cabin
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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
80% off second Sailor
RockStar Quarters suites from
$4,440
per Cabin
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Departing on:
 2025
Sat, Nov 29 - Fri, Dec 05
from (US$)$4,440Only 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
80% off second Sailor
Sea View cabins from
$1,744$2,706
per Cabin
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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
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11 nights
Brilliant Lady
80% off second Sailor
Insider cabins from
$2,532$3,918
per Cabin
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Departing on:

Cayman Coves & Jamaican Waterfalls
- Miami, Florida
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- The Beach Club at Bimini, Bahamas
- Miami, Florida
80% off second Sailor
Insider cabins from
$1,386$1,998
per Cabin
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Departing on:

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
80% off second Sailor
Insider cabins from
$1,412$2,170
per Cabin
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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
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8 nights
Brilliant Lady
80% off second Sailor
Insider cabins from
$2,064$3,192
per Cabin
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Resilient Caribbean Holidays
- Miami, Florida
- San Juan, Puerto Rico
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
80% off second Sailor
Sea View cabins from
$2,226$3,408
per Cabin
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Departing on:

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
80% off second Sailor
Insider cabins from
$1,946$3,046
per Cabin
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Scarlet Caribbean Holidays
- Miami, Florida
- Nassau, Bahamas
- The Beach Club at Bimini, Bahamas
- Miami, Florida
80% off second Sailor
Sea Terrace cabins from
$1,912$2,930
per Cabin
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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
80% off second Sailor
Insider cabins from
$3,942$6,340
per Cabin
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Departing on:

Resilient New Year's Ahoy!
- Miami, Florida
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- The Beach Club at Bimini, Bahamas
- Miami, Florida
80% off second Sailor
Insider cabins from
$3,616$5,712
per Cabin
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Departing on:

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
80% off second Sailor
Insider cabins from
$3,346$5,406
per Cabin
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Departing on:

Scarlet New Year's Ahoy!
- Miami, Florida
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
80% off second Sailor
Sea View cabins from
$3,290$5,136
per Cabin
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