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Explore 415 cruise vacations
Showing Loading cruise vacations: Caribbean, September 2025 - April 2027
Showing 252 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
$1,390$1,932
per Cabin
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70% off second Sailor
Insider cabins from
$1,390$1,932
per Cabin
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Departing on:

Mayan Sol
- Miami, Florida
- Costa Maya, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
Insider cabins from
$1,490$2,046
per Cabin
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70% off second Sailor
Insider cabins from
$1,490$2,046
per Cabin
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Departing on:

True Crime Voyage
- Miami, Florida
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Sea View cabins from
$1,490$2,082
per Cabin
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Departing on:

Scarlet's Haunted Halloween Soirée
- Barcelona
- Palma de Mallorca, Spain
- Casablanca, Morocco
- Funchal, Madeira, Portugal
- Santa Cruz de Tenerife, Spain
- Miami, Florida
70% off second Sailor
RockStar Quarters suites from
$10,800
per Cabin
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Departing on:
Thu, Oct 16 - Fri, Oct 31
from (US$)$10,800Only suites remaining

★
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
Insider cabins from
$2,384$3,436
per Cabin
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70% off second Sailor
Insider cabins from
$2,384$3,436
per Cabin
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Departing on:

Riviera Maya: Halloween Edition
- Miami, Florida
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$1,290$1,704
per Cabin
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Dominican Daze: Halloween Edition
- Miami, Florida
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Sea View cabins from
$1,692$2,388
per Cabin
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Departing on:

Valiant's Haunted Halloween Soirée
- Miami, Florida
- Key West, Florida
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Sea View cabins from
$1,592$2,226
per Cabin
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Departing on:

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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
70% off second Sailor
Sea View cabins from
$1,806$2,444
per Cabin
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Departing on:

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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 View cabins from
$2,088$2,958
per Cabin
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70% off second Sailor
Sea View cabins from
$2,088$2,958
per Cabin
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Departing on:

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
70% off second Sailor
Insider cabins from
$1,308$1,832
per Cabin
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Departing on:

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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
$3,818$5,606
per Cabin
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70% off second Sailor
Sea Terrace cabins from
$3,818$5,606
per Cabin
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Departing on:

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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
70% off second Sailor
Insider cabins from
$1,948$2,736
per Cabin
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Western Caribbean Charm
- Miami, Florida
- Costa Maya, Mexico
- Roatán, Honduras
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Sea View cabins from
$2,640$3,754
per Cabin
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Fire & Sunset Soirées
- Miami, Florida
- Key West, Florida
- The Beach Club at Bimini, Bahamas
- Miami, Florida
Insider cabins from
$1,192$1,626
per Cabin
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70% off second Sailor
Insider cabins from
$1,192$1,626
per Cabin
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Departing on:
* Port changes in place on select sailings — see full cruise details

★
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
70% off second Sailor
Insider cabins from
$1,666$2,318
per Cabin
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Departing on:

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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
70% off second Sailor
Sea View cabins from
$1,806$2,628
per Cabin
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Riviera Maya
- Miami, Florida
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$1,390$1,858
per Cabin
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Departing on:

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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
Insider cabins from
$1,904$2,726
per Cabin
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70% off second Sailor
Insider cabins from
$1,904$2,726
per Cabin
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Departing on:

Miami, Grand Turk (& back)
- Miami, Florida
- Grand Turk, Turks and Caicos
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$1,490$2,022
per Cabin
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Departing on:

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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
70% off second Sailor
Sea View cabins from
$1,806$2,526
per Cabin
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Departing on:

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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
70% off second Sailor
Insider cabins from
$1,666$2,400
per Cabin
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Departing on:

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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 View cabins from
$2,504$3,632
per Cabin
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70% off second Sailor
Sea View cabins from
$2,504$3,632
per Cabin
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Departing on:

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
70% off second Sailor
Sea View cabins from
$1,548$2,250
per Cabin
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Departing on:

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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
70% off second Sailor
Insider cabins from
$1,666$2,330
per Cabin
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Departing on:

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UP TO $600 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
70% off second Sailor
Insider cabins from
$1,904$2,766
per Cabin
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Departing on:

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UP TO $600 OFF
Aruban Sunsets & Calm Cayman Days
- Miami, Florida
- Oranjestad, Aruba
- Cartagena, Colombia
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- Miami, Florida
Insider cabins from
$2,620$3,786
per Cabin
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70% off second Sailor
Insider cabins from
$2,620$3,786
per Cabin
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Departing on:

★
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
70% off second Sailor
Sea View cabins from
$1,806$2,526
per Cabin
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Departing on:

★
UP TO $600 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
70% off second Sailor
Insider cabins from
$1,666$2,416
per Cabin
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Departing on:

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UP TO $600 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
$2,224$3,222
per Cabin
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70% off second Sailor
Insider cabins from
$2,224$3,222
per Cabin
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Departing on:

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UP TO $600 OFF
Resilient Caribbean Holidays
- Miami, Florida
- San Juan, Puerto Rico
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Sea View cabins from
$2,506$3,612
per Cabin
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Departing on:

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UP TO $600 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
70% off second Sailor
Sea View cabins from
$2,508$3,698
per Cabin
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Scarlet Caribbean Holidays
- Miami, Florida
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$1,890$2,638
per Cabin
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Departing on:
* Port changes in place on select sailings — see full cruise details

★
UP TO $600 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
$4,304$6,434
per Cabin
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70% off second Sailor
Insider cabins from
$4,304$6,434
per Cabin
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Departing on:

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UP TO $600 OFF
Resilient New Year's Ahoy!
- Miami, Florida
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Sea Terrace cabins from
$4,466$6,618
per Cabin
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Departing on:

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UP TO $600 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
70% off second Sailor
Sea View cabins from
$3,768$5,658
per Cabin
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Departing on:

Scarlet New Year's Ahoy!
- Miami, Florida
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$2,990$4,376
per Cabin
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Departing on:
* Port changes in place on select sailings — see full cruise details

★
UP TO $600 OFF
Aruban Sights & Antiguan Nights
- San Juan, Puerto Rico
- Oranjestad, Aruba
- Willemstad, Curaçao
- St. John's, Antigua
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$2,088$2,962
per Cabin
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Departing on:

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UP TO $600 OFF
Cozumel, Grand Cayman & Bimini
- Miami, Florida
- George Town, Grand Cayman
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Sea View cabins from
$2,226$3,116
per Cabin
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Departing on:

★
UP TO $600 OFF
Aruba, Bonaire, Colombia, Jamaica & More
- Miami, Florida
- Oranjestad, Aruba
- Kralendijk, Bonaire
- Cartagena, Colombia
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- Miami, Florida
Sea View cabins from
$3,498$5,130
per Cabin
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70% off second Sailor
Sea View cabins from
$3,498$5,130
per Cabin
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Departing on:

★
UP TO $600 OFF
Cayman Isles & Jamaican Miles
- Miami, Florida
- George Town, Grand Cayman
- Ocho Rios, Jamaica
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$1,526$2,102
per Cabin
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Departing on:

★
UP TO $600 OFF
Virgin Island Views & Saint Isle Blues
- San Juan, Puerto Rico
- Tortola, British Virgin Islands
- Bridgetown, Barbados
- Kingstown, St. Vincent
- Basseterre, St. Kitts and Nevis
- St. Croix, U.S. Virgin Islands
- San Juan, Puerto Rico
70% off second Sailor
Sea View cabins from
$2,086$3,078
per Cabin
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UP TO $600 OFF
St. Kitts, Barbados, Martinique & More
- San Juan, Puerto Rico
- Basseterre, St. Kitts and Nevis
- Bridgetown, Barbados
- Fort-de-France, Martinique
- St. John's, Antigua
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off second Sailor
Sea View cabins from
$2,086$3,066
per Cabin
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UP TO $600 OFF
Barbados, Antigua, BVI & More
- San Juan, Puerto Rico
- Tortola, British Virgin Islands
- Bridgetown, Barbados
- Fort-de-France, Martinique
- St. John's, Antigua
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off second Sailor
Sea View cabins from
$2,088$3,062
per Cabin
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Grand Turk, Puerto Plata & Bimini
- Miami, Florida
- The Beach Club at Bimini, Bahamas
- Puerto Plata, Dominican Republic
- Grand Turk, Turks and Caicos
- Miami, Florida
70% off second Sailor
Insider cabins from
$2,160$3,096
per Cabin
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UP TO $600 OFF
Antigua & the St. Isles
- San Juan, Puerto Rico
- Philipsburg, St. Maarten
- Basseterre, St. Kitts and Nevis
- St. John's, Antigua
- Castries, St. Lucia
- Charlotte Amalie, St. Thomas
- San Juan, Puerto Rico
70% off second Sailor
Sea View cabins from
$2,226$3,260
per Cabin
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UP TO $600 OFF
San Juan Sunrises & Dominican Dreams
- Miami, Florida
- Puerto Plata, Dominican Republic
- San Juan, Puerto Rico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Sea View cabins from
$1,948$2,766
per Cabin
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Departing on:

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UP TO $600 OFF
Magnetic Miami to Gorgeous George Town
- Miami, Florida
- Willemstad, Curaçao
- Oranjestad, Aruba
- Cartagena, Colombia
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- Miami, Florida
Sea View cabins from
$3,278$4,788
per Cabin
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70% off second Sailor
Sea View cabins from
$3,278$4,788
per Cabin
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Departing on:

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UP TO $600 OFF
St. Lucia, Barbados & More
- San Juan, Puerto Rico
- Philipsburg, St. Maarten
- Basseterre, St. Kitts and Nevis
- Castries, St. Lucia
- Bridgetown, Barbados
- Charlotte Amalie, St. Thomas
- San Juan, Puerto Rico
70% off second Sailor
Sea View cabins from
$2,226$3,262
per Cabin
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UP TO $600 OFF
Brilliant Valentine's Voyage
- Miami, Florida
- Puerto Plata, Dominican Republic
- San Juan, Puerto Rico
- Philipsburg, St. Maarten
- St. Croix, U.S. Virgin Islands
- Miami, Florida
Insider cabins from
$2,544$3,718
per Cabin
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70% off second Sailor
Insider cabins from
$2,544$3,718
per Cabin
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Departing on:

Scarlet Valentine's Voyage
- Miami, Florida
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Sea View cabins from
$1,890$2,702
per Cabin
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Departing on:

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UP TO $600 OFF
Resilient Valentine's Voyage
- Miami, Florida
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$2,086$2,962
per Cabin
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Departing on:

Valiant Valentine's Voyage
- San Juan, Puerto Rico
- Oranjestad, Aruba
- Willemstad, Curaçao
- St. Croix, U.S. Virgin Islands
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off second Sailor
Sea View cabins from
$2,226$3,284
per Cabin
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UP TO $600 OFF
Antigua, Martinique, & Barbados & More
- San Juan, Puerto Rico
- Philipsburg, St. Maarten
- Bridgetown, Barbados
- Fort-de-France, Martinique
- St. John's, Antigua
- Tortola, British Virgin Islands
- San Juan, Puerto Rico
70% off second Sailor
Sea View cabins from
$2,228$3,278
per Cabin
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UP TO $600 OFF
Quaint Castries to Elegant Antigua
- San Juan, Puerto Rico
- Basseterre, St. Kitts and Nevis
- Castries, St. Lucia
- Fort-de-France, Martinique
- St. John's, Antigua
- Tortola, British Virgin Islands
- San Juan, Puerto Rico
70% off second Sailor
Sea View cabins from
$2,800$4,168
per Cabin
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UP TO $600 OFF
Red Hot Sailing Club Voyage
- Miami, Florida
- Puerto Plata, Dominican Republic
- St. John's, Antigua
- Basseterre, St. Kitts and Nevis
- The Beach Club at Bimini, Bahamas
- Miami, Florida
Insider cabins from
$2,502$3,612
per Cabin
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70% off second Sailor
Insider cabins from
$2,502$3,612
per Cabin
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Costa Mayan Caves & Honduran Waves
- Miami, Florida
- Roatán, Honduras
- Costa Maya, Mexico
- Cozumel, Mexico
- Miami, Florida
70% off second Sailor
Sea View cabins from
$2,268$3,224
per Cabin
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UP TO $600 OFF
Sunsets in the Lesser Antilles
- San Juan, Puerto Rico
- Oranjestad, Aruba
- Willemstad, Curaçao
- Fort-de-France, Martinique
- Basseterre, St. Kitts and Nevis
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$1,806$2,628
per Cabin
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Departing on:

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UP TO $600 OFF
Puerto Rican Nights & St. Croix Delights
- Miami, Florida
- Puerto Plata, Dominican Republic
- San Juan, Puerto Rico
- St. Croix, U.S. Virgin Islands
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$2,960$4,316
per Cabin
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Cayman Isles & Bimini Beach Miles
- Miami, Florida
- George Town, Grand Cayman
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$1,490$2,048
per Cabin
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Miami to Grand Turk: Halloween Edition
- Miami, Florida
- Grand Turk, Turks and Caicos
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$2,040$2,904
per Cabin
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Mexico & Bimini: Halloween Edition
- Miami, Florida
- Cozumel, Mexico
- Costa Maya, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$1,908$2,660
per Cabin
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Scarlet's Haunted Halloween Soirée
- Miami, Florida
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$1,590$2,176
per Cabin
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Valiant's Haunted Halloween Soirée
- San Juan, Puerto Rico
- Willemstad, Curaçao
- Oranjestad, Aruba
- Fort-de-France, Martinique
- Basseterre, St. Kitts and Nevis
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$1,946$2,844
per Cabin
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November Nights in the Eastern Caribbean
- Miami, Florida
- Puerto Plata, Dominican Republic
- San Juan, Puerto Rico
- Tortola, British Virgin Islands
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$2,384$3,410
per Cabin
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Caribbean East: Virgin & Saint Isles
- San Juan, Puerto Rico
- Tortola, British Virgin Islands
- St. John's, Antigua
- Castries, St. Lucia
- Basseterre, St. Kitts and Nevis
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$1,550$2,182
per Cabin
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St. Isles & Sun-soaked Seas
- Miami, Florida
- Philipsburg, St. Maarten
- Tortola, British Virgin Islands
- Basseterre, St. Kitts and Nevis
- St. John's, Antigua
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$2,580$3,602
per Cabin
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Captivating Costa Maya & Cozumel Charm
- Miami, Florida
- Costa Maya, Mexico
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$1,788$2,476
per Cabin
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Thanksgiving: St. Isles, Aruba & Curaçao
- San Juan, Puerto Rico
- Charlotte Amalie, St. Thomas
- Willemstad, Curaçao
- Oranjestad, Aruba
- Basseterre, St. Kitts and Nevis
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$2,384$3,488
per Cabin
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Jamaican Waves & Bimini Breeze
- Miami, Florida
- Ocho Rios, Jamaica
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$1,590$2,152
per Cabin
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Antiguan Elegance & Sunny St. Isles
- San Juan, Puerto Rico
- Charlotte Amalie, St. Thomas
- Tortola, British Virgin Islands
- Basseterre, St. Kitts and Nevis
- St. John's, Antigua
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$1,948$2,778
per Cabin
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Departing on:

St. Maarten, Tortola, San Juan & more
- Miami, Florida
- Philipsburg, St. Maarten
- Tortola, British Virgin Islands
- St. Croix, U.S. Virgin Islands
- San Juan, Puerto Rico
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$2,580$3,584
per Cabin
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Pre-Holiday Caribbean Getaway
- Miami, Florida
- Philipsburg, St. Maarten
- Tortola, British Virgin Islands
- San Juan, Puerto Rico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$2,142$3,040
per Cabin
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Valiant Caribbean Holidays
- San Juan, Puerto Rico
- Basseterre, St. Kitts and Nevis
- Fort-de-France, Martinique
- Oranjestad, Aruba
- Willemstad, Curaçao
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$2,786$4,136
per Cabin
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Resilient Caribbean Holidays
- Miami, Florida
- Puerto Plata, Dominican Republic
- San Juan, Puerto Rico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$2,646$3,834
per Cabin
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Brilliant Caribbean Holidays
- Miami, Florida
- The Beach Club at Bimini, Bahamas
- Puerto Plata, Dominican Republic
- Miami, Florida
70% off second Sailor
Insider cabins from
$2,090$3,002
per Cabin
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Valiant New Year's Ahoy!
- San Juan, Puerto Rico
- Philipsburg, St. Maarten
- Fort-de-France, Martinique
- Bridgetown, Barbados
- Castries, St. Lucia
- St. John's, Antigua
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$3,488$5,198
per Cabin
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Resilient New Year's Ahoy!
- Miami, Florida
- George Town, Grand Cayman
- Ocho Rios, Jamaica
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$3,766$5,546
per Cabin
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Departing on:

Brilliant New Year's Ahoy!
- Miami, Florida
- Philipsburg, St. Maarten
- Basseterre, St. Kitts and Nevis
- Tortola, British Virgin Islands
- St. John's, Antigua
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$5,180$7,702
per Cabin
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★
UP TO $600 OFF
Cayman Isles & Jamaican Miles
- Miami, Florida
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$2,086$2,892
per Cabin
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Puerto Rico to Aruba, Bonaire & More
- San Juan, Puerto Rico
- Oranjestad, Aruba
- Willemstad, Curaçao
- Kralendijk, Bonaire
- Fort-de-France, Martinique
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$2,226$3,156
per Cabin
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San Juan & St. Isles: Valentine’s Voyage
- Miami, Florida
- Philipsburg, St. Maarten
- Tortola, British Virgin Islands
- St. Croix, U.S. Virgin Islands
- San Juan, Puerto Rico
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$2,780$3,892
per Cabin
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Key West & Bimini: Valentine’s Voyage
- Miami, Florida
- Key West, Florida
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$1,352$1,818
per Cabin
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Lesser Antilles: Valentine's Day
- San Juan, Puerto Rico
- Oranjestad, Aruba
- Willemstad, Curaçao
- Fort-de-France, Martinique
- Basseterre, St. Kitts and Nevis
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$2,088$2,976
per Cabin
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PR, DR & Bimini: Valentine’s Voyage
- Miami, Florida
- San Juan, Puerto Rico
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$2,590$3,676
per Cabin
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Saint Isles & The Greater Antilles
- San Juan, Puerto Rico
- Tortola, British Virgin Islands
- Castries, St. Lucia
- Bridgetown, Barbados
- Roseau, Dominica
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$2,088$2,962
per Cabin
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★
UP TO $600 OFF
Saint (Isles) & Seas of the Caribbean
- San Juan, Puerto Rico
- Philipsburg, St. Maarten
- Bridgetown, Barbados
- Castries, St. Lucia
- St. John's, Antigua
- Tortola, British Virgin Islands
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$2,086$2,950
per Cabin
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Barbados, Dominica & St. Isle Spring
- San Juan, Puerto Rico
- Charlotte Amalie, St. Thomas
- Bridgetown, Barbados
- Kingstown, St. Vincent
- Roseau, Dominica
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$2,386$3,418
per Cabin
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Colorful Curaçao, Aruba & Antigua
- San Juan, Puerto Rico
- Willemstad, Curaçao
- Oranjestad, Aruba
- St. John's, Antigua
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off second Sailor
Sea Terrace cabins from
$3,150$4,598
per Cabin
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San Juan to Miami: Dominican Daze
- San Juan, Puerto Rico
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$1,492$2,054
per Cabin
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Grand Cayman & Bimini Beach Club
- Miami, Florida
- The Beach Club at Bimini, Bahamas
- George Town, Grand Cayman
- Miami, Florida
70% off second Sailor
Insider cabins from
$1,540$2,150
per Cabin
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