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Explore 407 cruise vacations
Showing Loading cruise vacations: Caribbean, June 2025 - April 2027
70% off 2nd Sailor + Free balcony upgrade ends in…
Showing 265 cruise vacations that match your search
Showing 265 cruise vacations that match your search
Fire & Sunset Soirées
- Miami, Florida
- Key West, Florida
- The Beach Club at Bimini, Bahamas
- Miami, Florida
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4 nights
Valiant Lady, Scarlet Lady, Resilient Lady & Brilliant Lady
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
* Port changes in place on select sailings — see full cruise details
DEAL
Grand Cayman, Costa Maya & More
- Miami, Florida
- George Town, Grand Cayman
- Costa Maya, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
Grand Turk, Puerto Plata & More
- Miami, Florida
- Puerto Plata, Dominican Republic
- Grand Turk, Turks and Caicos
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
Riviera Maya
- Miami, Florida
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
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Dominican Daze
- Miami, Florida
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
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5 nights
Valiant Lady, Scarlet Lady, Resilient Lady & Brilliant Lady
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
Virgin Voyages Comedy Fest from Miami
- Miami, Florida
- Costa Maya, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
Mayan Sol
- Miami, Florida
- Costa Maya, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
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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
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
Brilliant Lady Miami MerMaiden
- Miami, Florida
- Philipsburg, St. Maarten
- Tortola, British Virgin Islands
- The Beach Club at Bimini, Bahamas
- Miami, Florida
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8 nights
Brilliant Lady
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
Riviera Maya: Halloween Edition
- Miami, Florida
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
Dominican Daze: Halloween Edition
- Miami, Florida
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
Valiant's Haunted Halloween Soirée
- Miami, Florida
- Key West, Florida
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
Honduras, Mexico & Bahamas
- Miami, Florida
- Roatán, Honduras
- Costa Maya, Mexico
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
Western Caribbean: From Miami to Bimini
- Miami, Florida
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- The Beach Club at Bimini, Bahamas
- Miami, Florida
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7 nights
Brilliant Lady
SWING INTO SUMMER: 70% off 2nd Sailor
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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
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
Colorful Curaçao to the Charming Caymans
- Miami, Florida
- Oranjestad, Aruba
- Willemstad, Curaçao
- Cartagena, Colombia
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- Miami, Florida
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12 nights
Brilliant Lady
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
Western Caribbean Charm
- Miami, Florida
- Costa Maya, Mexico
- Roatán, Honduras
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
San Juan Sunrises & Dominican Dreams
- Miami, Florida
- San Juan, Puerto Rico
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
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DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
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DEAL
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
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8 nights
Brilliant Lady
SWING INTO SUMMER: 70% off 2nd Sailor
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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
SWING INTO SUMMER: 70% off 2nd Sailor
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DEAL
Cayman Coves & Jamaican Waterfalls
- Miami, Florida
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
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
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9 nights
Brilliant Lady
SWING INTO SUMMER: 70% off 2nd Sailor
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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
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
San Juan, Samaná & Bimini
- Miami, Florida
- San Juan, Puerto Rico
- Samaná, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
Aruban Sunsets & Calm Cayman Days
- Miami, Florida
- Oranjestad, Aruba
- Cartagena, Colombia
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- Miami, Florida
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11 nights
Brilliant Lady
SWING INTO SUMMER: 70% off 2nd Sailor
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DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
Brilliant Caribbean Holidays
- Miami, Florida
- Grand Turk, Turks and Caicos
- Puerto Plata, Dominican Republic
- San Juan, Puerto Rico
- Samaná, Dominican Republic
- Miami, Florida
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8 nights
Brilliant Lady
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
DEAL
Resilient Caribbean Holidays
- Miami, Florida
- San Juan, Puerto Rico
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
Scarlet Caribbean Holidays
- Miami, Florida
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
* Port changes in place on select sailings — see full cruise details
DEAL
Brilliant New Year's Ahoy!
- Miami, Florida
- Grand Turk, Turks and Caicos
- St. John's, Antigua
- Basseterre, St. Kitts and Nevis
- San Juan, Puerto Rico
- Miami, Florida
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9 nights
Brilliant Lady
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
Resilient New Year's Ahoy!
- Miami, Florida
- George Town, Grand Cayman
- Ocho Rios, Jamaica
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
Scarlet New Year's Ahoy!
- Miami, Florida
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
* Port changes in place on select sailings — see full cruise details
DEAL
Aruban Sights & Antiguan Nights
- San Juan, Puerto Rico
- Oranjestad, Aruba
- Willemstad, Curaçao
- St. John's, Antigua
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
DEAL
Cozumel, Grand Cayman & Bimini
- Miami, Florida
- George Town, Grand Cayman
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
Aruba, Bonaire, Colombia, Jamaica & More
- Miami, Florida
- Oranjestad, Aruba
- Kralendijk, Bonaire
- Cartagena, Colombia
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- Miami, Florida
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11 nights
Brilliant Lady
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
DEAL
Cayman Isles & Jamaican Miles
- Miami, Florida
- George Town, Grand Cayman
- Ocho Rios, Jamaica
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
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DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
Grand Turk, Puerto Plata & Bimini
- Miami, Florida
- The Beach Club at Bimini, Bahamas
- Puerto Plata, Dominican Republic
- Grand Turk, Turks and Caicos
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
San Juan Sunrises & Dominican Dreams
- Miami, Florida
- Puerto Plata, Dominican Republic
- San Juan, Puerto Rico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
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DEAL
Magnetic Miami to Gorgeous George Town
- Miami, Florida
- Willemstad, Curaçao
- Oranjestad, Aruba
- Cartagena, Colombia
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- Miami, Florida
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11 nights
Brilliant Lady
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
DEAL
Cayman Coves & Jamaican Waterfalls
- Miami, Florida
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
Aruba, Curaçao and the St. Isles
- San Juan, Puerto Rico
- Oranjestad, Aruba
- Willemstad, Curaçao
- St. Croix, U.S. Virgin Islands
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
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
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9 nights
Brilliant Lady
SWING INTO SUMMER: 70% off 2nd Sailor
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Costa Mayan Caves & Honduran Waves
- Miami, Florida
- Roatán, Honduras
- Costa Maya, Mexico
- Cozumel, Mexico
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
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DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
Puerto Plata, San Juan & Tortola
- Miami, Florida
- Puerto Plata, Dominican Republic
- San Juan, Puerto Rico
- Tortola, British Virgin Islands
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
Cayman Isles & Bimini Beach Miles
- Miami, Florida
- George Town, Grand Cayman
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
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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
SWING INTO SUMMER: 70% off 2nd Sailor
Mexico & Bimini: Halloween Edition
- Miami, Florida
- Cozumel, Mexico
- Costa Maya, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
Scarlet's Haunted Halloween Soirée
- Miami, Florida
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
Caribbean East: Virgin & Saint Isles
- San Juan, Puerto Rico
- Tortola, British Virgin Islands
- Basseterre, St. Kitts and Nevis
- St. John's, Antigua
- Castries, St. Lucia
- San Juan, Puerto Rico
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
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Captivating Costa Maya & Cozumel Charm
- Miami, Florida
- Costa Maya, Mexico
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
Jamaican Waves & Bimini Breeze
- Miami, Florida
- Ocho Rios, Jamaica
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
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DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
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DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
Valiant Caribbean Holidays
- San Juan, Puerto Rico
- Basseterre, St. Kitts and Nevis
- Fort-de-France, Martinique
- Oranjestad, Aruba
- Willemstad, Curaçao
- San Juan, Puerto Rico
SWING INTO SUMMER: 70% off 2nd Sailor
Resilient Caribbean Holidays
- Miami, Florida
- Puerto Plata, Dominican Republic
- San Juan, Puerto Rico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
Brilliant Caribbean Holidays
- Miami, Florida
- The Beach Club at Bimini, Bahamas
- Puerto Plata, Dominican Republic
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
Cayman Isles & Jamaican Miles
- Miami, Florida
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
Key West & Bimini: Valentine’s Voyage
- Miami, Florida
- Key West, Florida
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
PR, DR & Bimini: Valentine’s Voyage
- Miami, Florida
- San Juan, Puerto Rico
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
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
SWING INTO SUMMER: 70% off 2nd Sailor
DEAL
Colorful Curaçao, Aruba & Antigua
- San Juan, Puerto Rico
- Willemstad, Curaçao
- Oranjestad, Aruba
- St. John's, Antigua
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
SWING INTO SUMMER: 70% off 2nd Sailor
San Juan to Miami: Dominican Daze
- San Juan, Puerto Rico
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
SWING INTO SUMMER: 70% off 2nd Sailor