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Showing 33cruise vacations: Caribbean,November 2024 - October 2026
Departs San Juan, Puerto Rico
Showing 33 cruise vacations that match your search
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San Juan to St. Lucia: Holiday Edition
San JuanTortolaPhilipsburgBridgetownFort-de-FranceCastriesBasseterreSan Juan
Insider cabins from
Price$2,804
per Cabin
8 nights
Resilient Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,804
per Cabin
Departing on:
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Saint (Isles) & Seas of the Caribbean
San JuanTortolaBridgetownCastriesSt. John'sPhilipsburgSan Juan
Insider cabins from
Price$1,946
per Cabin
7 nights
Resilient Lady & 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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Resilient Caribbean Holidays
San JuanPhilipsburgBridgetownCastriesFort-de-FranceBasseterreSan Juan
Insider cabins from
Price$2,592
per Cabin
7 nights
Resilient Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,592
per Cabin
Departing on:
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Resilient New Year's Ahoy
San JuanTortolaBridgetownCastriesSt. John'sPhilipsburgSan Juan
Insider cabins from
Price$3,238
per Cabin
7 nights
Resilient Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,238
per Cabin
Departing on:
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Sunsets in the Lesser Antilles
San JuanOranjestadWillemstadFort-de-FranceBasseterreSan Juan
Insider cabins from
Price$2,226
per Cabin
7 nights
Resilient Lady & Valiant 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$1,980
per Cabin
10 nights
Resilient Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,980
per Cabin
Departing on:
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Idyllic Caribbean Isles & Colombia
San JuanCartagenaWillemstadOranjestadCastriesSt. John'sPhilipsburgSan Juan
Insider cabins from
Price$2,178
per Cabin
11 nights
Resilient Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,178
per Cabin
Departing on:
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Trending
Resilient Valentine's Voyage
San JuanTortolaBridgetownCastriesSt. John'sPhilipsburgSan Juan
Insider cabins from
Price$2,648
per Cabin
7 nights
Resilient Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,648
per Cabin
Departing on:
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San Juan, Barbados & Beyond
San JuanPhilipsburgCastriesBridgetownFort-de-FranceBasseterreSan Juan
Insider cabins from
Price$2,366
per Cabin
7 nights
Resilient Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,366
per Cabin
Departing on:
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Puerto Rican Daze & Caribbean Nights
San JuanTortolaSt. John'sBasseterreFort-de-FranceCastriesBridgetownKingstownSan Juan
Insider cabins from
Price$2,182
per Cabin
10 nights
Resilient Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,182
per Cabin
Departing on:
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Colombia & Caribbean Islands
San JuanCartagenaOranjestadWillemstadRoseauSt. John'sPhilipsburgSan Juan
Insider cabins from
Price$2,400
per Cabin
11 nights
Resilient Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,400
per Cabin
Departing on:
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Sunny Miles of Tropical Isles
San JuanPhilipsburgBridgetownCastriesFort-de-FranceBasseterreSan Juan
Insider cabins from
Price$1,948
per Cabin
7 nights
Valiant Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
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Sun-Soaked Seas & Saint Isles
San JuanTortolaBasseterreSt. John'sFort-de-FranceBridgetownCastriesPhilipsburgSan Juan
Insider cabins from
Price$2,780
per Cabin
10 nights
Valiant Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,780
per Cabin
Departing on:
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Cartagena & Caribbean Faves
San JuanCartagenaWillemstadOranjestadFort-de-FranceSt. John'sPhilipsburgSan Juan
Insider cabins from
Price$3,060
per Cabin
11 nights
Valiant Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,060
per Cabin
Departing on:
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St. Lucia, St. Maarten, Barbados & More
San JuanBasseterreCastriesRoseauBridgetownPhilipsburgSan Juan
Insider cabins from
Price$1,946
per Cabin
7 nights
Valiant Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,946
per Cabin
Departing on:
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Valiant Caribbean Holidays
San JuanPhilipsburgBasseterreSt. John'sCastriesTortolaSan Juan
Insider cabins from
Price$2,368
per Cabin
7 nights
Valiant Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,368
per Cabin
Departing on:
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Valiant New Year’s Ahoy!
San JuanPhilipsburgBasseterreCastriesBridgetownSt. CroixSan Juan
Insider cabins from
Price$3,768
per Cabin
7 nights
Valiant Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,768
per Cabin
Departing on:
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Aruban Sights & Antiguan Nights
San JuanOranjestadWillemstadSt. John'sPhilipsburgSan Juan
Insider cabins from
Price$2,086
per Cabin
7 nights
Valiant Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,086
per Cabin
Departing on:
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Virgin Island Views & Saint Isle Blues
San JuanTortolaBridgetownKingstownBasseterreSt. CroixSan Juan
Insider cabins from
Price$1,946
per Cabin
7 nights
Valiant Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,946
per Cabin
Departing on:
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St. Kitts, Barbados, Martinique & More
San JuanBasseterreBridgetownFort-de-FranceSt. John'sPhilipsburgSan Juan
Insider cabins from
Price$1,946
per Cabin
7 nights
Valiant Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,946
per Cabin
Departing on:
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Barbados, Antigua, BVI & More
San JuanTortolaBridgetownFort-de-FranceSt. John'sPhilipsburgSan Juan
Insider cabins from
Price$1,946
per Cabin
7 nights
Valiant Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,946
per Cabin
Departing on:
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Quintessential Caribbean Highlights
San JuanPhilipsburgBasseterreSt. John'sFort-de-FranceCastriesKingstownBridgetownSan Juan
Insider cabins from
Price$2,780
per Cabin
10 nights
Valiant Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,780
per Cabin
Departing on:
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Cartagena, Aruba, Antigua & More
San JuanCartagenaWillemstadOranjestadSt. John'sSt. CroixPhilipsburgSan Juan
Insider cabins from
Price$3,058
per Cabin
11 nights
Valiant Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,058
per Cabin
Departing on:
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Antigua, Martinique, & Barbados & More
San JuanPhilipsburgBridgetownFort-de-FranceSt. John'sTortolaSan Juan
Insider cabins from
Price$2,086
per Cabin
7 nights
Valiant Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,086
per Cabin
Departing on:
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Quaint Castries to Elegant Antigua
San JuanBasseterreCastriesFort-de-FranceSt. John'sTortolaSan Juan
Insider cabins from
Price$2,228
per Cabin
7 nights
Valiant Lady
& free drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,228
per Cabin
Departing on: