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Windstar Cruises to Caribbean - All 2024/2025

Save up to 75% on Windstar cruises

As a large-scale seller of Windstar Cruises to Caribbean - All 2024/2025, we are able to offer you unbeatable prices and unparalleled value. With cruise line volume buys plus our low everyday prices you can save up to 75% versus the brochure price! Once you have found the discounted Windstar cruise of your choice, please call our cruise consultants to book your vacation and save money with our first-rate personalized service! Book your Windstar cruise today with AffordableTours.com, your discounted cruise headquarters.

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Cruises

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Sail Date Cruise Line Ship Destination Departs Length Price You Save Discounts
10 reviews
Itinerary Map/Ship Image
WindstarWind StarTransatlanticBridgetownLisbon15 NightsBridgetown | Lisbon$1,599
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)
24 reviews
Itinerary Map/Ship Image
WindstarWind SurfCaribbean - EasternPhilipsburgLisbon14 NightsLisbon | Ponta Delgada | St. Maarten$1,399
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)
15 reviews
Itinerary Map/Ship Image
WindstarStar PrideCanadaMontrealSan Juan22 NightsBar Harbor | Basseterre | Boston | Cap aux Meules | Gaspe | Gustavia | Halifax | Hamilton | Louisbourg | Lunenburg | Montreal | Portland | Quebec City | San Juan | St. George's | Virgin Gorda$6,479
Up To $750 Onboard Credit
 
15 reviews
Itinerary Map/Ship Image
WindstarStar PrideCaribbeanBostonSan Juan11 NightsBasseterre | Boston | Gustavia | Hamilton | San Juan | St. George's | Virgin Gorda$2,699
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)

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15 reviews
Itinerary Map/Ship Image
WindstarStar PrideCaribbean - EasternSan JuanSan Juan13 NightsBequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | Virgin Gorda$4,099
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)
15 reviews
Itinerary Map/Ship Image
WindstarStar PrideCaribbean - EasternSan JuanSan Juan6 NightsGustavia | Jost Van Dyke, Great Harbour | Little Bay | San Juan | St. Maarten | Virgin Gorda$2,299
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)
10 reviews
Itinerary Map/Ship Image
WindstarWind StarTransatlanticLisbonBridgetown14 NightsBridgetown | Lisbon$2,199
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)
15 reviews
Itinerary Map/Ship Image
WindstarStar PrideCaribbean - EasternSan JuanSan Juan7 NightsBequia | Les Saintes | Pigeon Island | San Juan | St. George's | St. Maarten$2,699
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)
15 reviews
Itinerary Map/Ship Image
WindstarStar PrideCaribbeanSan JuanSan Juan14 NightsBequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | St. Thomas | Virgin Gorda / Prickly Pear$4,099
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)
11 reviews
Itinerary Map/Ship Image
WindstarWind SpiritTransatlanticLisbonBridgetown14 NightsBridgetown | Lisbon$2,499
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)
15 reviews
Itinerary Map/Ship Image
WindstarStar PrideCaribbean - EasternSan JuanSan Juan14 NightsBequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | St. Thomas | Virgin Gorda$3,899
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)
15 reviews
Itinerary Map/Ship Image
WindstarStar PrideCaribbean - EasternSan JuanSan Juan7 NightsGustavia | Jost Van Dyke, Great Harbour | Little Bay | San Juan | St. Maarten | St. Thomas | Virgin Gorda$2,299
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)
10 reviews
Itinerary Map/Ship Image
WindstarWind StarCentral AmericaBridgetownPuerto Caldera18 NightsBalboa / Fuerte Amador | Bequia | Bridgetown | Cartagena | Colón | Golfo Dulce | Isla Parida | Kralendijk | Mayreau | Oranjestad | Puerto Caldera | Quepos | St. George's | Willemstad$4,699
Up To $500 Onboard Credit
 
10 reviews
Itinerary Map/Ship Image
WindstarWind StarCaribbean - SouthernBridgetownColon11 NightsBequia | Bridgetown | Cartagena | Colón | Kralendijk | Mayreau | Oranjestad | St. George's | Willemstad$2,999
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)
15 reviews
Itinerary Map/Ship Image
WindstarStar PrideCaribbean - EasternSan JuanSan Juan14 NightsBequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | St. Thomas | Virgin Gorda$3,999
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)
15 reviews
Itinerary Map/Ship Image
WindstarStar PrideCaribbean - EasternSan JuanSan Juan7 NightsBequia | Les Saintes | Pigeon Island | San Juan | St. George's | St. Maarten$2,499
Up To $250 Onboard Credit
 
11 reviews
Itinerary Map/Ship Image
WindstarWind SpiritCaribbeanBridgetownBridgetown10 NightsBridgetown | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | Soper's Hole | Virgin Gorda / Prickly Pear$2,899
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)
15 reviews
Itinerary Map/Ship Image
WindstarStar PrideCaribbean - EasternSan JuanSan Juan7 NightsGustavia | Jost Van Dyke, Great Harbour | Little Bay | San Juan | St. Maarten | St. Thomas | Virgin Gorda$2,399
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)
10 reviews
Itinerary Map/Ship Image
WindstarWind StarCaribbeanColonPuerto Caldera11 NightsBalboa / Fuerte Amador | Colón | Golfo Dulce | Isla Parida | La Fortuna (Arenal), Costa Rica | Panama Canal | Puerto Caldera | Quepos | Santa Elena (Monteverde)$5,199
Up To $750 Onboard Credit
 
10 reviews
Itinerary Map/Ship Image
WindstarWind StarCaribbeanPuerto CalderaColon11 NightsBalboa / Fuerte Amador | Colón | Golfo Dulce | Isla Parida | La Fortuna (Arenal), Costa Rica | Panama Canal | Puerto Caldera | Quepos | San Jose | Santa Elena (Monteverde)$5,199
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)

Learn More About Windstar Cruises

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