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Explore 399 cruise vacations
Showing Loading cruise vacations: Caribbean, July 2025 - August 2026
2 Sailors , 1 Cabin
Sails Resilient Lady
Showing 47 cruise vacations that match your search
Showing 47 cruise vacations that match your search

Western Caribbean Charm
- Miami, Florida
- Costa Maya, Mexico
- Roatán, Honduras
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off 2nd Sailor

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 2nd Sailor
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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
70% off 2nd Sailor
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San Juan, Samaná & Bimini
- Miami, Florida
- San Juan, Puerto Rico
- Samaná, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off 2nd Sailor
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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
70% off 2nd Sailor

Resilient New Year's Ahoy!
- Miami, Florida
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off 2nd Sailor

Cozumel, Grand Cayman & Bimini
- Miami, Florida
- George Town, Grand Cayman
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off 2nd Sailor

Cayman Isles & Jamaican Miles
- Miami, Florida
- George Town, Grand Cayman
- Ocho Rios, Jamaica
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off 2nd Sailor
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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 2nd Sailor
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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
70% off 2nd Sailor

Resilient Valentine's Voyage
- Miami, Florida
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off 2nd Sailor

Costa Mayan Caves & Honduran Waves
- Miami, Florida
- Roatán, Honduras
- Costa Maya, Mexico
- Cozumel, Mexico
- Miami, Florida
70% off 2nd Sailor

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 2nd Sailor

Miami, Grand Turk (& back)
- Miami, Florida
- Grand Turk, Turks and Caicos
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off 2nd Sailor
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Fire & Sunset Soirées
- Miami, Florida
- Key West, Florida
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off 2nd Sailor
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Riviera Maya
- Miami, Florida
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off 2nd Sailor
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Dominican Daze
- Miami, Florida
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off 2nd Sailor
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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 2nd Sailor
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Mayan Sol
- Miami, Florida
- Costa Maya, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off 2nd Sailor