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Windstar Cruises to Caribbean - Eastern 2025/2026

Save up to 80% on Windstar cruises

As a large-scale seller of Windstar Cruises to Caribbean - Eastern 2025/2026, 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 80% 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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Sail Date Cruise Line Ship Destination Departs Length Price You Save Discounts
17 reviews
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7 night Caribbean (San Juan & the Virgin Islands (Oct 26 2025))WindstarStar PrideCaribbeanSan JuanSan Juan7 NightsBasseterre | CRUZ BAY, ST. JOHN, Virgin Islands (U.S.) | Gustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | San Juan$2,762
Up To $300 Onboard Credit
Suite!
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17 reviews
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7 night Caribbean (San Juan & the Virgin Islands (Nov 2 2025))WindstarStar PrideCaribbean - EasternSan JuanSan Juan7 NightsBasseterre | CRUZ BAY, ST. JOHN, Virgin Islands (U.S.) | Gustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | San Juan$2,962
Up To $300 Onboard Credit
Suite!
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17 reviews
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14 night Star Collector Voyages (Lovely Leewards (Nov 2 2025))WindstarStar PrideCaribbean - SouthernSan JuanSan Juan14 NightsBasseterre | Bequia | CRUZ BAY, ST. JOHN, Virgin Islands (U.S.) | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Marigot, St. Martin | Philipsburg, St. Maarten | Pigeon Island | San Juan | St. George's$4,893
Up To $500 Onboard Credit
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17 reviews
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7 night Caribbean (San Juan & the Virgin Islands (Nov 9 2025))WindstarStar PrideCaribbean - SouthernSan JuanSan Juan7 NightsBequia | Les Saintes | Marigot, St. Martin | Pigeon Island | San Juan | St. George's$2,730
Shipboard Credit Per Person ($150)
Shipboard Credit Per Person ($150)View ItineraryGet FREE Quote

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17 reviews
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14 night Star Collector Voyages (Lovely Leewards (Nov 9 2025))WindstarStar PrideCaribbean - SouthernSan JuanSan Juan14 NightsBasseterre | Bequia | CRUZ BAY, ST. JOHN, Virgin Islands (U.S.) | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Marigot, St. Martin | Philipsburg, St. Maarten | Pigeon Island | San Juan | St. George's$4,393
Shipboard Credit Per Person ($150)
Shipboard Credit Per Person ($150)View ItineraryGet FREE Quote
17 reviews
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7 night Caribbean (San Juan & the Virgin Islands (Nov 16 2025))WindstarStar PrideCaribbean - EasternSan JuanSan Juan7 NightsBasseterre | CRUZ BAY, ST. JOHN, Virgin Islands (U.S.) | Gustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | San Juan$2,762
Shipboard Credit Per Person ($150)
Shipboard Credit Per Person ($150)View ItineraryGet FREE Quote
17 reviews
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14 night Star Collector Voyages (Lovely Leewards (Nov 16 2025))WindstarStar PrideCaribbean - EasternSan JuanSan Juan14 NightsBasseterre | Bequia | CRUZ BAY, ST. JOHN, Virgin Islands (U.S.) | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Marigot, St. Martin | Philipsburg, St. Maarten | Pigeon Island | San Juan | St. George's$4,393
Shipboard Credit Per Person ($150)
Shipboard Credit Per Person ($150)View ItineraryGet FREE Quote
25 reviews
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19 night Star Collector Voyages (Hearty Ports & Rum Punches - A Transatlantic Crossing (Nov 18 2025))WindstarWind SurfTransatlanticLisbonPhilipsburg19 NightsGustavia | Jost Van Dyke, Great Harbour | Lisbon | Philipsburg, St. Maarten | Soper's Hole$3,680
Shipboard Credit Per Person ($150)
Shipboard Credit Per Person ($150)View ItineraryGet FREE Quote
17 reviews
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14 night Star Collector Voyages (Lovely Leewards (Nov 23 2025))WindstarStar PrideCaribbean - EasternSan JuanSan Juan14 NightsBasseterre | Bequia | CRUZ BAY, ST. JOHN, Virgin Islands (U.S.) | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Marigot, St. Martin | Philipsburg, St. Maarten | Pigeon Island | San Juan | St. George's$4,393
Shipboard Credit Per Person ($150)
Shipboard Credit Per Person ($150)View ItineraryGet FREE Quote
17 reviews
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7 night Caribbean (San Juan & the Virgin Islands (Nov 30 2025))WindstarStar PrideCaribbean - SouthernSan JuanSan Juan7 NightsBasseterre | CRUZ BAY, ST. JOHN, Virgin Islands (U.S.) | Gustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | San Juan$2,762
Shipboard Credit Per Person ($150)
Shipboard Credit Per Person ($150)View ItineraryGet FREE Quote
17 reviews
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13 night Star Collector Voyages (Star Collector: Beaches & Bastions of the BVI and Spanish Caribbean (Nov 30 2025))WindstarStar PrideCaribbeanSan JuanColon13 NightsBasseterre | Cartagena | Colón | CRUZ BAY, ST. JOHN, Virgin Islands (U.S.) | Gustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | San Blas, Panama | San Juan | Santo Domingo$4,298
Up To $500 Onboard Credit
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25 reviews
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5 night Caribbean (Barefoot Break in the British Virgin Islands (Dec 2 2025))WindstarWind SurfCaribbean - EasternPhilipsburgPhilipsburg5 NightsGustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | Soper's Hole$2,150
Up To $250 Onboard Credit
Onboard Credit!
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25 reviews
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12 night Star Collector Voyages (Ivory Beaches & Sapphire Seas of the Caribbean (Dec 2 2025))WindstarWind SurfCaribbean - EasternPhilipsburgPhilipsburg12 NightsBasseterre | Charlestown | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Mayreau | Philipsburg, St. Maarten | Roseau | Soper's Hole$3,502
Up To $500 Onboard Credit
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25 reviews
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7 night Caribbean (Classic Caribbean (Dec 7 2025))WindstarWind SurfCaribbean - EasternPhilipsburgPhilipsburg7 NightsBasseterre | Charlestown | Gustavia | Les Saintes | Mayreau | Philipsburg, St. Maarten | Roseau$2,351
Up To $250 Onboard Credit
Onboard Credit!
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25 reviews
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14 night Star Collector Voyages (Caribbean Explorations (Dec 7 2025))WindstarWind SurfCaribbean - SouthernPhilipsburgPhilipsburg14 NightsBasseterre | Charlestown | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Mayreau | Philipsburg, St. Maarten | Road Bay | Roseau | Soper's Hole$3,819
Up To $500 Onboard Credit
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17 reviews
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13 night Star Collector Voyages (Star Collector: Coffee, Canal & Callaloo - Central America, Columbia & the Caribbean (Dec 7 2025))WindstarStar PrideCaribbeanSan JuanPuerto Caldera13 NightsBalboa / Fuerte Amador | Cartagena | Colón | Golfo Dulce | Isla Parida | Panama Canal | Puerto Caldera | Quepos | San Blas, Panama | San Juan | Santo Domingo$4,593
Up To $500 Onboard Credit
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25 reviews
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14 night Star Collector Voyages (Caribbean Explorations (Dec 14 2025))WindstarWind SurfCaribbean - SouthernPhilipsburgPhilipsburg14 NightsBasseterre | Charlestown | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Mayreau | Philipsburg, St. Maarten | Road Bay | Roseau | Soper's Hole$4,619
Shipboard Credit Per Person ($150)
Shipboard Credit Per Person ($150)View ItineraryGet FREE Quote
25 reviews
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6 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway (Dec 14 2025))WindstarWind SurfCaribbeanPhilipsburgPhilipsburg6 NightsFalmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | Road Bay | Soper's Hole$2,467
Up To $250 Onboard Credit
Onboard Credit!
View ItineraryGet FREE Quote
25 reviews
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7 night Caribbean (Classic Caribbean (Dec 21 2025))WindstarWind SurfCaribbean - EasternPhilipsburgPhilipsburg7 NightsBasseterre | Charlestown | Gustavia | Les Saintes | Mayreau | Philipsburg, St. Maarten | Roseau$2,951
Shipboard Credit Per Person ($150)
Shipboard Credit Per Person ($150)View ItineraryGet FREE Quote
25 reviews
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14 night Star Collector Voyages (Caribbean Explorations (Dec 21 2025))WindstarWind SurfCaribbean - EasternPhilipsburgPhilipsburg14 NightsBasseterre | Charlestown | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Mayreau | Philipsburg, St. Maarten | Road Bay | Roseau | Soper's Hole$5,119
Shipboard Credit Per Person ($150)
Shipboard Credit Per Person ($150)View ItineraryGet FREE Quote

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