Windstar Cruises to Caribbean - Western 2022/2023
Save up to 75% on Windstar cruises
As a large-scale seller of Windstar Cruises to Caribbean - Western 2022/2023, 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.

Sail Date | Cruise Line | Ship | Destination | Departs | Length | Price | You Save | Discounts | |
---|---|---|---|---|---|---|---|---|---|
10 reviews ![]() | Nov 03, 2022 | Windstar | Star Pride | San Juan | San Juan | 16 Nights | Basseterre | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | St. Thomas | Virgin Gorda | $3,599 Up To $500 Onboard Credit | Suite! |
10 reviews ![]() | Nov 03, 2022 | Windstar | Star Pride | San Juan | San Juan | 9 Nights | Basseterre | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | San Juan | St. Maarten | St. Thomas | Virgin Gorda | $2,799 Up To $300 Onboard Credit | |
10 reviews ![]() | Nov 12, 2022 | Windstar | Star Pride | San Juan | San Juan | 14 Nights | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | St. Thomas | Virgin Gorda | $3,599 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
10 reviews ![]() | Nov 19, 2022 | Windstar | Star Pride | San Juan | San Juan | 14 Nights | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | St. Thomas | Virgin Gorda | $3,599 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
10 reviews ![]() | Nov 19, 2022 | Windstar | Star Pride | San Juan | San Juan | 7 Nights | Gustavia | 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) |
8 reviews ![]() | Nov 22, 2022 | Windstar | Wind Star | Bridgetown | Puerto Caldera | 18 Nights | Balboa / Fuerte Amador | Bequia | Bridgetown | Cartegena | Colón | Golfo Dulce | Isla Parida | Kralendijk | Mayreau | Oranjestad | Panama Canal | Puerto Caldera | Quepos | St. George's | Willemstad | $4,999 Up To $750 Onboard Credit | Onboard Credit! |
8 reviews ![]() | Nov 22, 2022 | Windstar | Wind Star | Bridgetown | Colon | 11 Nights | Bequia | Bridgetown | Cartegena | Colón | Kralendijk | Mayreau | Oranjestad | St. George's | Willemstad | $2,799 Up To $300 Onboard Credit | Onboard Credit! |
10 reviews ![]() | Nov 26, 2022 | Windstar | Star Pride | San Juan | San Juan | 14 Nights | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | St. Thomas | Virgin Gorda | $4,399 Up To $500 Onboard Credit | |
10 reviews ![]() | Dec 03, 2022 | Windstar | Star Pride | San Juan | San Juan | 7 Nights | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | San Juan | St. Maarten | St. Thomas | Virgin Gorda | $2,799 Up To $300 Onboard Credit | Suite! |
8 reviews ![]() | Dec 03, 2022 | Windstar | Wind Star | Colon | Puerto Caldera | 11 Nights | Balboa / Fuerte Amador | Colón | Golfo Dulce | Isla Parida | La Fortuna (Arenal), Costa Rica | Panama Canal | Puerto Caldera | Quepos | Santa Elena (Monteverde) | $4,899 Up To $500 Onboard Credit | Onboard Credit! |
8 reviews ![]() | Dec 06, 2022 | Windstar | Wind Star | Puerto Caldera | Colon | 11 Nights | Balboa / Fuerte Amador | Colón | Golfo Dulce | Isla Parida | La Fortuna (Arenal), Costa Rica | Panama Canal | Puerto Caldera | Quepos | San Jose | Santa Elena (Monteverde) | $4,799 Up To $500 Onboard Credit | Onboard Credit! |
8 reviews ![]() | Dec 10, 2022 | Windstar | Wind Star | Puerto Caldera | Colon | 7 Nights | Balboa / Fuerte Amador | Colón | Golfo Dulce | Isla Parida | Panama Canal | Puerto Caldera | Quepos | $2,699 Up To $300 Onboard Credit | Onboard Credit! |
24 reviews ![]() | Dec 10, 2022 | Windstar | Wind Surf | Philipsburg | Philipsburg | 17 Nights | Anse Mitan | Basseterre | Bridgetown | Castries | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Roseau | Soper's Hole | St. Maarten | Virgin Gorda | $4,699 Up To $500 Onboard Credit | Onboard Credit! |
10 reviews ![]() | Dec 10, 2022 | Windstar | Star Pride | San Juan | San Juan | 10 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | San Juan | St. George's | St. Thomas | Virgin Gorda | $3,099 Up To $500 Onboard Credit | Suite! |
2 reviews ![]() | Dec 17, 2022 | Windstar | Star Legend | Miami | Miami | 10 Nights | Belize City | Costa Maya | Cozumel | Key West | Miami | Roatan | Santo Tomas de Castillo | $3,599 Up To $500 Onboard Credit | |
24 reviews ![]() | Dec 17, 2022 | Windstar | Wind Surf | Philipsburg | Philipsburg | 10 Nights | Anse Mitan | Bridgetown | Castries | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Soper's Hole | St. Maarten | Virgin Gorda | $3,299 Up To $500 Onboard Credit | |
8 reviews ![]() | Dec 17, 2022 | Windstar | Wind Star | Colon | Puerto Caldera | 10 Nights | Bahia Drake | Bahia Herradura | Balboa / Fuerte Amador | Colón | Golfo Dulce | Isla Parida | Panama Canal | Puerto Caldera | Quepos | $3,399 Up To $500 Onboard Credit | Onboard Credit! |
10 reviews ![]() | Dec 20, 2022 | Windstar | Star Pride | San Juan | San Juan | 7 Nights | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | San Juan | St. Maarten | St. Thomas | Virgin Gorda | $2,399 Up To $250 Onboard Credit | Suite! |
8 reviews ![]() | Dec 27, 2022 | Windstar | Wind Star | Puerto Caldera | Colon | 11 Nights | Bahia Drake | Bahia Herradura | Balboa / Fuerte Amador | Colón | Golfo Dulce | Isla Parida | Panama Canal | Playa Flamingo | Puerto Caldera | Quepos | $3,699 Up To $500 Onboard Credit | Onboard Credit! |
10 reviews ![]() | Dec 27, 2022 | Windstar | Star Pride | San Juan | San Juan | 11 Nights | Basseterre | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | San Juan | St. George's | St. Thomas | Virgin Gorda | $3,699 Up To $500 Onboard Credit | Suite! |
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