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Showing 89cruise vacations: Caribbean,November 2024 - October 2025
2 Sailors , 1 Cabin
Showing 89 cruise vacations that match your search
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Riviera Maya
Miami, FloridaCozumel (Playa del Carmen)Beach Club at BiminiMiami, Florida
Insider cabins from
Price$493
per Sailor
5 nights
Valiant Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
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Dominican Daze
Miami, FloridaPuerto PlataBeach Club at BiminiMiami, Florida
Insider cabins from
Price$982
per Sailor
5 nights
Valiant Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
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SAVINGS TO WRITE HOME ABOUT

80% off your 2nd Sailor + free drinks

Always Included Luxury covers your WiFi, tips & gratuities, all dining, & more.

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Eastern Caribbean Antilles
Miami, FloridaPuerto PlataSan JuanSt. CroixBeach Club at BiminiMiami, Florida
Insider cabins from
Price$1,033
per Sailor
8 nights
Scarlet Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
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Saint (Isles) & Seas of the Caribbean
San JuanTortolaBridgetownCastriesSt. John'sPhilipsburgSan Juan
Insider cabins from
Price$1,305
per Sailor
7 nights
Resilient Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
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Valiant Caribbean Holidays
Miami, FloridaNassauPuerto PlataBeach Club at BiminiMiami, Florida
Insider cabins from
Price$1,135
per Sailor
6 nights
Valiant Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,135
per Sailor
Departing on:
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Resilient Caribbean Holidays
San JuanPhilipsburgBridgetownCastriesFort-de-FranceBasseterreSan Juan
Insider cabins from
Price$1,394
per Sailor
7 nights
Resilient Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,394
per Sailor
Departing on:
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Fire & Sunset Soirées
Miami, FloridaKey West, FloridaBeach Club at BiminiMiami, Florida
Insider cabins from
Price$717
per Sailor
4 nights
Valiant Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
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Resilient New Year's Ahoy
San JuanTortolaBridgetownCastriesSt. John'sPhilipsburgSan Juan
Insider cabins from
Price$2,486
per Sailor
7 nights
Resilient Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,486
per Sailor
Departing on:
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Sunsets in the Lesser Antilles
San JuanOranjestadWillemstadFort-de-FranceBasseterreSan Juan
Insider cabins from
Price$1,439
per Sailor
7 nights
Resilient Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
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Trending
Western Caribbean Charm
Miami, FloridaRoatánCosta MayaBeach Club at BiminiMiami, Florida
Insider cabins from
Price$589
per Sailor
6 nights
Scarlet Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
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San Juan, St. Vincent, Barbados & More
San JuanTortolaBasseterreSt. John'sFort-de-FranceBridgetownCastriesKingstownSan Juan
Insider cabins from
Price$981
per Sailor
10 nights
Resilient Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$981
per Sailor
Departing on:
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Idyllic Caribbean Isles & Colombia
San JuanCartagenaWillemstadOranjestadCastriesSt. John'sPhilipsburgSan Juan
Insider cabins from
Price$1,085
per Sailor
11 nights
Resilient Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,085
per Sailor
Departing on:
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San Juan, Barbados & Beyond
San JuanPhilipsburgCastriesBridgetownFort-de-FranceBasseterreSan Juan
Insider cabins from
Price$1,584
per Sailor
7 nights
Resilient Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,584
per Sailor
Departing on:
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Puerto Rican Daze & Caribbean Nights
San JuanTortolaSt. John'sBasseterreFort-de-FranceCastriesBridgetownKingstownSan Juan
Insider cabins from
Price$990
per Sailor
10 nights
Resilient Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$990
per Sailor
Departing on:
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Colombia & Caribbean Islands
San JuanCartagenaOranjestadWillemstadRoseauSt. John'sPhilipsburgSan Juan
Insider cabins from
Price$1,082
per Sailor
11 nights
Resilient Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,082
per Sailor
Departing on:
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Sunny Daze in Puerto Plata & Nassau
Miami, FloridaPuerto PlataNassauMiami, Florida
Insider cabins from
Price$1,102
per Sailor
5 nights
Valiant Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,102
per Sailor
Departing on:
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Mayan Sol
Miami, FloridaCosta MayaBeach Club at BiminiMiami, Florida
Insider cabins from
Price$1,035
per Sailor
5 nights
Valiant Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
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Grand Cayman, Costa Maya & More
Miami, FloridaGeorge TownCosta MayaBeach Club at BiminiMiami, Florida
Insider cabins from
Price$1,721
per Sailor
7 nights
Valiant Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,721
per Sailor
Departing on:
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Grand Turk, Puerto Plata & More
Miami, FloridaPuerto PlataGrand TurkBeach Club at BiminiMiami, Florida
Insider cabins from
Price$1,797
per Sailor
7 nights
Valiant Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,797
per Sailor
Departing on: