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Explore 410 cruise vacations
Showing Loading cruise vacations: Caribbean, September 2025 - October 2027
Showing 291 cruise vacations that match your search
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Mayan Sol
- Miami, Florida
- Costa Maya, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
Insider cabins from
$1,190$1,560
per Cabin
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70% off second Sailor
Insider cabins from
$1,190$1,560
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
Insider cabins from
$1,290$1,774
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
$9,870
per Cabin
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Departing on:
Thu, Oct 16 - Fri, Oct 31
from (US$)$9,870Only 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
$1,190$1,550
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
Insider cabins from
$1,290$1,772
per Cabin
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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
$1,514$2,104
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
Insider cabins from
$1,514
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
$1,304
per Cabin
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Dominican Daze
- Miami, Florida
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
Sea Terrace cabins from
$1,284
per Cabin
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70% off second Sailor
Sea Terrace cabins from
$1,284
per Cabin
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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
Insider cabins from
$2,604
per Cabin
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70% off second Sailor
Insider cabins from
$2,604
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
$2,226$3,166
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
Insider cabins from
$1,428$1,892
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
$1,272$1,694
per Cabin
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70% off second Sailor
Insider cabins from
$1,272$1,694
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
$1,516
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
Insider cabins from
$1,522
per Cabin
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Riviera Maya
- Miami, Florida
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
Insider cabins from
$1,082
per Cabin
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70% off second Sailor
Insider cabins from
$1,082
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
$2,720$3,982
per Cabin
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70% off second Sailor
Insider cabins from
$2,720$3,982
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
Insider cabins from
$1,640$2,258
per Cabin
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70% off second Sailor
Insider cabins from
$1,640$2,258
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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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
$1,518
per Cabin
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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
Insider cabins from
$1,952
per Cabin
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70% off second Sailor
Insider cabins from
$1,952
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
Insider cabins from
$1,298
per Cabin
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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
$1,522
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
$1,740
per Cabin
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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
$2,386
per Cabin
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70% off second Sailor
Insider cabins from
$2,386
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
Insider cabins from
$1,518
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
$1,518
per Cabin
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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
Sea View cabins from
$2,864$4,206
per Cabin
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70% off second Sailor
Sea View cabins from
$2,864$4,206
per Cabin
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Departing on:

★
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
Insider cabins from
$1,516
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
Insider cabins from
$1,526
per Cabin
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Scarlet Caribbean Holidays
- Miami, Florida
- Nassau, Bahamas
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Sea View cabins from
$1,752$2,488
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
$3,190$4,684
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
$2,366$3,392
per Cabin
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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
$2,368$3,334
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
$3,720$5,470
per Cabin
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70% off second Sailor
Sea View cabins from
$3,720$5,470
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
Insider cabins from
$1,806$2,648
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
Insider cabins from
$1,806$2,634
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
$2,228$3,278
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
$2,520$3,650
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
Insider cabins from
$1,806$2,614
per Cabin
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Departing on:

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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
Insider cabins from
$1,666$2,334
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
$4,840$7,192
per Cabin
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70% off second Sailor
Sea View cabins from
$4,840$7,192
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
Insider cabins from
$1,946$2,832
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
$3,026$4,458
per Cabin
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70% off second Sailor
Insider cabins from
$3,026$4,458
per Cabin
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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
$2,092$3,010
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
$2,228$3,180
per Cabin
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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
Insider cabins from
$1,948$2,854
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
$2,366$3,492
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
$2,366$3,502
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
Sea View cabins from
$3,584$5,274
per Cabin
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70% off second Sailor
Sea View cabins from
$3,584$5,274
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
$2,508$3,594
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
$2,088$3,060
per Cabin
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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
$3,280$4,810
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
Insider cabins from
$1,640$2,246
per Cabin
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70% off second Sailor
Insider cabins from
$1,640$2,246
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
$2,280$3,276
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
$2,148$3,030
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
$1,790$2,484
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
$2,226$3,274
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
$2,706$3,904
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
$1,788$2,550
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
$2,980$4,218
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
$2,030$2,846
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
$2,706$3,982
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
$1,792$2,460
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
$2,226$3,208
per Cabin
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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
$3,382$4,816
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
$2,502$3,594
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
$3,068$4,568
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
$2,928$4,266
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
$2,290$3,310
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
$3,766$5,628
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
$4,046$5,978
per Cabin
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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
$5,382$8,010
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
$2,366$3,324
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
$2,546$3,648
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
$3,182$4,508
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
$1,514$2,066
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
$2,366$3,406
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
$2,870$4,108
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
$2,366$3,392
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
$2,368$3,382
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
$2,704$3,910
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
$3,432$5,030
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
$1,690$2,360
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
$1,740$2,458
per Cabin
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