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Showing 226cruise vacations: Caribbean,December 2024 - October 2026
Showing 226 cruise vacations that match your search
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Eastern Caribbean Antilles
Miami, FloridaPuerto PlataSan JuanSt. CroixBeach Club at BiminiMiami, Florida
Insider cabins from
Price$1,744
per Cabin
8 nights
Scarlet Lady
+ $200 in 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$1,668
per Cabin
7 nights
Resilient Lady & Valiant Lady
+ $200 in 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$1,286
per Cabin
5 nights
Valiant Lady, Scarlet Lady & Resilient Lady
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
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Scarlet New Year's Ahoy!
Miami, FloridaPuerto PlataSan JuanSt. CroixBeach Club at BiminiMiami, Florida
Sea Terrace cabins from
Price$5,746
per Cabin
8 nights
Scarlet Lady
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Sea Terrace cabins from
Price$5,746
per Cabin
Departing on:
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Sunsets in the Lesser Antilles
San JuanOranjestadWillemstadFort-de-FranceBasseterreSan Juan
Insider cabins from
Price$1,806
per Cabin
7 nights
Resilient Lady & Valiant Lady
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
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Fire & Sunset Soirées
Miami, FloridaKey West, FloridaBeach Club at BiminiMiami, Florida
Insider cabins from
Price$1,192
per Cabin
4 nights
Valiant Lady, Scarlet Lady & Resilient Lady
+ $100 in 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
Sea View cabins from
Price$3,402
per Cabin
10 nights
Resilient Lady
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Sea View cabins from
Price$3,402
per Cabin
Departing on:
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Riviera Maya
Miami, FloridaCozumel (Playa del Carmen)Beach Club at BiminiMiami, Florida
Insider cabins from
Price$1,288
per Cabin
5 nights
Valiant Lady, Scarlet Lady & Resilient Lady
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
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Western Caribbean Charm
Miami, FloridaCosta MayaRoatánBeach Club at BiminiMiami, Florida
Insider cabins from
Price$1,538
per Cabin
6 nights
Scarlet Lady & Resilient Lady
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
* Port changes in place on select sailings — see full cruise details
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Idyllic Caribbean Isles & Colombia
San JuanCartagenaWillemstadOranjestadCastriesSt. John'sPhilipsburgSan Juan
Insider cabins from
Price$2,310
per Cabin
11 nights
Resilient Lady
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,310
per Cabin
Departing on:
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Resilient Valentine's Voyage
San JuanTortolaBridgetownCastriesSt. John'sPhilipsburgSan Juan
Sea View cabins from
Price$3,206
per Cabin
7 nights
Resilient Lady
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Sea View cabins from
Price$3,206
per Cabin
Departing on:
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Scarlet Valentine's Voyage
Miami, FloridaPuerto PlataSan JuanSt. CroixBeach Club at BiminiMiami, Florida
Insider cabins from
Price$2,320
per Cabin
8 nights
Scarlet Lady
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,320
per Cabin
Departing on:
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Valiant Valentine's Voyage
Miami, FloridaPuerto PlataBeach Club at BiminiMiami, Florida
Sea View cabins from
Price$1,690
per Cabin
5 nights
Valiant Lady
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Sea View cabins from
Price$1,690
per Cabin
Departing on:
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San Juan, Barbados & Beyond
San JuanPhilipsburgCastriesBridgetownFort-de-FranceBasseterreSan Juan
Insider cabins from
Price$2,506
per Cabin
7 nights
Resilient Lady
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,506
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
+ $300 in 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$2,824
per Cabin
11 nights
Resilient Lady
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,824
per Cabin
Departing on:
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Sunny Daze in Puerto Plata & Nassau
Miami, FloridaPuerto PlataNassauMiami, Florida
Sea Terrace cabins from
Price$2,490
per Cabin
5 nights
Valiant Lady
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Sea Terrace cabins from
Price$2,490
per Cabin
Departing on:
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A Virgin Celebration Voyage (Miami)
Miami, FloridaCozumel (Playa del Carmen)Beach Club at BiminiMiami, Florida
Insider cabins from
Price$1,690
per Cabin
5 nights
Valiant Lady
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,690
per Cabin
Departing on:
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Mayan Sol
Miami, FloridaCosta MayaBeach Club at BiminiMiami, Florida
Insider cabins from
Price$1,490
per Cabin
5 nights
Valiant Lady & Resilient Lady
+ $100 in 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$2,788
per Cabin
7 nights
Valiant Lady
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,788
per Cabin
Departing on:
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Grand Turk, Puerto Plata & More
Miami, FloridaPuerto PlataGrand TurkBeach Club at BiminiMiami, Florida
Insider cabins from
Price$3,290
per Cabin
7 nights
Valiant Lady
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,290
per Cabin
Departing on:
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Virgin Voyages Comedy Fest from Miami
Miami, FloridaCosta MayaBeach Club at BiminiMiami, Florida
Insider cabins from
Price$1,692
per Cabin
5 nights
Valiant Lady
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,692
per Cabin
Departing on:
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Brilliant Lady Miami MerMaiden
Miami, FloridaPhilipsburgTortolaBeach Club at BiminiMiami, Florida
Insider cabins from
Price$3,186
per Cabin
8 nights
Brilliant Lady
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,186
per Cabin
Departing on:
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Riviera Maya: Halloween Edition
Miami, FloridaCozumel (Playa del Carmen)Beach Club at BiminiMiami, Florida
Insider cabins from
Price$1,490
per Cabin
5 nights
Valiant Lady
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,490
per Cabin
Departing on:
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Dominican Daze: Halloween Edition
Miami, FloridaPuerto PlataBeach Club at BiminiMiami, Florida
Insider cabins from
Price$1,590
per Cabin
5 nights
Valiant Lady
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,590
per Cabin
Departing on:
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Valiant's Haunted Halloween Soirée
Miami, FloridaKey West, FloridaBeach Club at BiminiMiami, Florida
Insider cabins from
Price$1,280
per Cabin
4 nights
Valiant Lady
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,280
per Cabin
Departing on:
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Honduras, Mexico & Bahamas
Miami, FloridaRoatánCosta MayaCozumel (Playa del Carmen)Beach Club at BiminiMiami, Florida
Insider cabins from
Price$2,088
per Cabin
7 nights
Scarlet Lady
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,088
per Cabin
Departing on:
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Western Caribbean: From Miami to Bimini
Miami, FloridaOcho RiosGeorge TownBeach Club at BiminiMiami, Florida
Insider cabins from
Price$2,086
per Cabin
7 nights
Brilliant Lady
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,086
per Cabin
Departing on:
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One-way to SJ: DR, St. Maarten & BVI
Miami, FloridaPuerto PlataPhilipsburgTortolaSan Juan
Insider cabins from
Price$1,788
per Cabin
6 nights
Valiant Lady
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,788
per Cabin
Departing on:
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Colorful Curacao to the Charming Caymans
Miami, FloridaOranjestadWillemstadCartagenaOcho RiosGeorge TownMiami, Florida
Insider cabins from
Price$3,096
per Cabin
12 nights
Brilliant Lady
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,096
per Cabin
Departing on:
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San Juan Sunrises & Dominican Dreams
Miami, FloridaSan JuanPuerto PlataBeach Club at BiminiMiami, Florida
Insider cabins from
Price$2,086
per Cabin
7 nights
Resilient Lady
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
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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
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
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From Miami to St. Croix
Miami, FloridaPuerto PlataSan JuanPhilipsburgSt. CroixMiami, Florida
Insider cabins from
Price$2,384
per Cabin
8 nights
Brilliant Lady
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
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Miami, Grand Turk (& back)
Miami, FloridaGrand TurkBeach Club at BiminiMiami, Florida
Insider cabins from
Price$1,590
per Cabin
5 nights
Scarlet Lady & Resilient Lady
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
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Cayman Coves & Jamaican Waterfalls
Miami, FloridaOcho RiosGeorge TownBeach Club at BiminiMiami, Florida
Insider cabins from
Price$1,948
per Cabin
7 nights
Resilient Lady
+ $200 in 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
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,780
per Cabin
Departing on:
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Miami to San Juan
Miami, FloridaGrand TurkSt. John'sBasseterreSan JuanMiami, Florida
Insider cabins from
Price$2,324
per Cabin
9 nights
Brilliant Lady
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
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San Juan, Samaná & Bimini
Miami, FloridaSan JuanSamanáBeach Club at BiminiMiami, Florida
Insider cabins from
Price$1,948
per Cabin
7 nights
Resilient Lady
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
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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
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,060
per Cabin
Departing on:
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Aruban Sunsets & Calm Cayman Days
Miami, FloridaOranjestadCartagenaOcho RiosGeorge TownMiami, Florida
Insider cabins from
Price$2,838
per Cabin
11 nights
Brilliant Lady
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
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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
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,946
per Cabin
Departing on:
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Brilliant Caribbean Holidays
Miami, FloridaGrand TurkPuerto PlataSan JuanSamanáMiami, Florida
Insider cabins from
Price$3,186
per Cabin
8 nights
Brilliant Lady
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,186
per Cabin
Departing on:
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Resilient Caribbean Holidays
Miami, FloridaSan JuanPuerto PlataBeach Club at BiminiMiami, Florida
Insider cabins from
Price$2,786
per Cabin
7 nights
Resilient Lady
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,786
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
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,368
per Cabin
Departing on:
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Scarlet Caribbean Holidays
Miami, FloridaNassauBeach Club at BiminiMiami, Florida
Insider cabins from
Price$1,512
per Cabin
4 nights
Scarlet Lady
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,512
per Cabin
Departing on:
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Brilliant New Year's Ahoy!
Miami, FloridaGrand TurkSt. John'sBasseterreSan JuanMiami, Florida
Insider cabins from
Price$4,664
per Cabin
9 nights
Brilliant Lady
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$4,664
per Cabin
Departing on:
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Resilient New Year's Ahoy!
Miami, FloridaOcho RiosGeorge TownBeach Club at BiminiMiami, Florida
Insider cabins from
Price$3,766
per Cabin
7 nights
Resilient Lady
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,766
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
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,768
per Cabin
Departing on:
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Scarlet New Year's Ahoy!
Miami, FloridaCozumel (Playa del Carmen)Beach Club at BiminiMiami, Florida
Insider cabins from
Price$2,918
per Cabin
5 nights
Scarlet Lady
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,918
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
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,086
per Cabin
Departing on:
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Cozumel, Grand Cayman & Bimini
Miami, FloridaGeorge TownCozumel (Playa del Carmen)Beach Club at BiminiMiami, Florida
Insider cabins from
Price$1,948
per Cabin
7 nights
Resilient Lady
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,948
per Cabin
Departing on:
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Miami to the Cayman Islands
Miami, FloridaOranjestadKralendijkCartagenaOcho RiosGeorge TownMiami, Florida
Insider cabins from
Price$2,840
per Cabin
11 nights
Brilliant Lady
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,840
per Cabin
Departing on:
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Cayman Isles & Jamaican Miles
Miami, FloridaGeorge TownOcho RiosBeach Club at BiminiMiami, Florida
Insider cabins from
Price$1,948
per Cabin
7 nights
Resilient Lady
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Picture of the cruise
Virgin Island Views & Saint Isle Blues
San JuanTortolaBridgetownKingstownBasseterreSt. CroixSan Juan
Insider cabins from
Price$1,946
per Cabin
7 nights
Valiant Lady
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,946
per Cabin
Departing on:
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Grand Turk Tranquility & St. Croix Charm
Miami, FloridaGrand TurkPuerto PlataSan JuanSt. CroixMiami, Florida
Insider cabins from
Price$2,384
per Cabin
8 nights
Brilliant Lady
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,384
per Cabin
Departing on:
Picture of the cruise
St. Kitts, Barbados, Martinique & More
San JuanBasseterreBridgetownFort-de-FranceSt. John'sPhilipsburgSan Juan
Insider cabins from
Price$1,946
per Cabin
7 nights
Valiant Lady
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,946
per Cabin
Departing on:
Picture of the cruise
Barbados, Antigua, BVI & More
San JuanTortolaBridgetownFort-de-FranceSt. John'sPhilipsburgSan Juan
Insider cabins from
Price$1,946
per Cabin
7 nights
Valiant Lady
+ $200 in 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
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,780
per Cabin
Departing on:
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Magnetic Miami to Gorgeous George Town
Miami, FloridaWillemstadOranjestadCartagenaOcho RiosGeorge TownMiami, Florida
Insider cabins from
Price$2,840
per Cabin
11 nights
Brilliant Lady
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,840
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
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,058
per Cabin
Departing on:
Picture of the cruise
Antigua, Martinique, & Barbados & More
San JuanPhilipsburgBridgetownFort-de-FranceSt. John'sTortolaSan Juan
Insider cabins from
Price$2,086
per Cabin
7 nights
Valiant Lady
+ $200 in 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
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,228
per Cabin
Departing on:
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Gorgeous Antigua, St. Kitts & Bimini
Miami, FloridaPuerto PlataSt. John'sBasseterreBeach Club at BiminiMiami, Florida
Insider cabins from
Price$2,682
per Cabin
9 nights
Brilliant Lady
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,682
per Cabin
Departing on:
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Costa Mayan Caves & Honduran Waves
Miami, FloridaCosta MayaRoatánCozumel (Playa del Carmen)Miami, Florida
Insider cabins from
Price$1,910
per Cabin
6 nights
Resilient Lady
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,910
per Cabin
Departing on:
Picture of the cruise
Puerto Rican Nights & St. Croix Delights
Miami, FloridaPuerto PlataSan JuanSt. CroixBeach Club at BiminiMiami, Florida
Insider cabins from
Price$2,544
per Cabin
8 nights
Resilient Lady
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,544
per Cabin
Departing on:
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Panama Canal & Pacific Wonders
Miami, FloridaCartagenaColónPanama Canal (Cruising)PuntarenasPuerto QuetzalCabo San LucasLos Angeles, California
Insider cabins from
Price$6,370
per Cabin
16 nights
Brilliant Lady
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$6,370
per Cabin
Departing on:
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Puerto Plata, San Juan & Tortola
Miami, FloridaPuerto PlataSan JuanTortolaMiami, Florida
Insider cabins from
Price$2,228
per Cabin
7 nights
Scarlet Lady
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,228
per Cabin
Departing on: