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Windstar Cruises to Caribbean - Southern 2024/2025

Save up to 80% on Windstar cruises

As a large-scale seller of Windstar Cruises to Caribbean - Southern 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 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
16 reviews
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14 night Star Collector Voyages (Lovely Leewards (Nov 16 2024))WindstarStar PrideCaribbean - EasternSan JuanSan Juan14 NightsBasseterre | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Philipsburg, St. Maarten | Pigeon Island | San Juan | St. George's | St. Thomas$6,408
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
11 reviews
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11 night Caribbean (Colombian & Southern Caribbean Coastlines (Nov 19 2024))WindstarWind StarCaribbean - SouthernBridgetownColon11 NightsBequia | Bridgetown | Cartagena | Colón | Kralendijk | Mayreau | Oranjestad | St. George's | Willemstad$2,700
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
16 reviews
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14 night Star Collector Voyages (Lovely Leewards (Nov 23 2024))WindstarStar PrideCaribbean - EasternSan JuanSan Juan14 NightsBasseterre | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Philipsburg, St. Maarten | Pigeon Island | San Juan | St. George's | St. Thomas$5,208
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
16 reviews
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7 night Caribbean (Windward Islands Surf & Sunsets (Nov 23 2024))WindstarStar PrideCaribbean - SouthernSan JuanSan Juan7 NightsBequia | Les Saintes | Philipsburg, St. Maarten | Pigeon Island | San Juan | St. George's$2,118
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote

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11 reviews
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10 night Caribbean (Hidden Treasures of the Lesser Antilles (Nov 27 2024))WindstarWind SpiritCaribbean - EasternBridgetownBridgetown10 NightsBasseterre | Bridgetown | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Soper's Hole$4,077
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
16 reviews
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7 night Caribbean (San Juan & the Virgin Islands (Nov 30 2024))WindstarStar PrideCaribbean - SouthernSan JuanSan Juan7 NightsBasseterre | Gustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | San Juan | St. Thomas$3,368
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
16 reviews
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14 night Star Collector Voyages (White Sands of the Windwards (Dec 7 2024))WindstarStar PrideCaribbean - EasternSan JuanOranjestad14 NightsBasseterre | Bridgetown | Gustavia | Man-O-War Bay | Mayreau | Oranjestad | Pigeon Island | Roseau | San Juan | Soufriere | St. George's | St. Thomas | Willemstad$3,930
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
16 reviews
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7 night Caribbean (Winter Antilles Escape (Dec 7 2024))WindstarStar PrideCaribbean - SouthernSan JuanBridgetown7 NightsBasseterre | Bridgetown | Gustavia | Pigeon Island | Roseau | San Juan | St. George's | St. Thomas$2,200
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
11 reviews
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14 night Star Collector Voyages (Windward Treasures: An Antilles Odyssey (Dec 7 2024))WindstarWind SpiritCaribbean - SouthernBridgetownBridgetown14 NightsAnse Mitan | Basseterre | Bequia | Bridgetown | Castries | Kingstown | Les Saintes | Mayreau | Pigeon Island | Roseau | St. George's | The Pitons$4,468
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
11 reviews
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7 night Caribbean (Jewels of the Windward Islands (Dec 7 2024))WindstarWind SpiritCaribbean - SouthernBridgetownBridgetown7 NightsBequia | Bridgetown | Castries | Kingstown | Mayreau | Pigeon Island | St. George's | The Pitons$2,651
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
16 reviews
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14 night Star Collector Voyages (Windward Islands & Spanish New World (Dec 14 2024))WindstarStar PrideCaribbean - SouthernBridgetownFuerte Amador14 NightsBocas del Toro | Bridgetown | Cartagena | Man-O-War Bay | Mayreau | Oranjestad | San Blas | Soufriere | St. George's | Willemstad$5,085
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
16 reviews
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7 night Caribbean (Windward Ways & Tobago Cays (Dec 14 2024))WindstarStar PrideCaribbean - SouthernBridgetownOranjestad7 NightsBridgetown | Man-O-War Bay | Mayreau | Oranjestad | Soufriere | St. George's | Willemstad$2,098
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
11 reviews
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14 night Star Collector Voyages (Windward Treasures: An Antilles Odyssey (Dec 14 2024))WindstarWind SpiritCaribbean - SouthernBridgetownBridgetown14 NightsAnse Mitan | Basseterre | Bequia | Bridgetown | Castries | Kingstown | Les Saintes | Mayreau | Pigeon Island | Roseau | St. George's | The Pitons$5,068
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
11 reviews
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7 night Caribbean (Windward Island Delights (Dec 14 2024))WindstarWind SpiritCaribbean - SouthernBridgetownBridgetown7 NightsAnse Mitan | Basseterre | Bridgetown | Les Saintes | Pigeon Island | Roseau$2,310
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
11 reviews
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7 night Caribbean (Jewels of the Windward Islands (Dec 21 2024))WindstarWind SpiritCaribbean - SouthernBridgetownBridgetown7 NightsBequia | Bridgetown | Castries | Kingstown | Mayreau | Pigeon Island | St. George's | The Pitons$3,151
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
25 reviews
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14 night Star Collector Voyages (Caribbean Explorations (Dec 21 2024))WindstarWind SurfCaribbeanPhilipsburgPhilipsburg14 Nights$6,769
Up To $750 Onboard Credit
 View ItineraryGet FREE Quote
16 reviews
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7 night Caribbean (Windward Ways & Tobago Cays (Jan 4 2025))WindstarStar PrideCaribbean - SouthernOranjestadBridgetown7 NightsBridgetown | Man-O-War Bay | Mayreau | Oranjestad | Soufriere | St. George's | Willemstad$2,696
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
25 reviews
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14 night Star Collector Voyages (Caribbean Explorations (Jan 4 2025))WindstarWind SurfCaribbean - SouthernPhilipsburgPhilipsburg14 NightsBasseterre | Charlestown | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Philipsburg, St. Maarten | Pigeon Island | Road Bay | Roseau | Soper's Hole$4,439
Up To $500 Onboard Credit
Onboard Credit!
View ItineraryGet FREE Quote
11 reviews
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14 night Star Collector Voyages (Windward Treasures: An Antilles Odyssey (Jan 4 2025))WindstarWind SpiritCaribbean - SouthernBridgetownBridgetown14 NightsAnse Mitan | Basseterre | Bequia | Bridgetown | Castries | Kingstown | Les Saintes | Mayreau | Pigeon Island | Roseau | St. George's | The Pitons$5,068
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
11 reviews
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7 night Caribbean (Jewels of the Windward Islands (Jan 4 2025))WindstarWind SpiritCaribbean - SouthernBridgetownBridgetown7 NightsBequia | Bridgetown | Castries | Kingstown | Mayreau | Pigeon Island | St. George's | The Pitons$2,450
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote

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