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 | ||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|
25 reviews  | 5 night Caribbean (Barefoot Break in the British Virgin Islands (Dec 2 2025)) | Dec 02, 2025 | Windstar | Wind Surf | Philipsburg | Philipsburg | 5 Nights | Gustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | Soper's Hole | $2,150 Up To $250 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
25 reviews | 7 night Caribbean (Classic Caribbean (Mar 21 2026)) | Mar 21, 2026 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Mayreau | Philipsburg, St. Maarten | Roseau | $2,451 Up To $250 Onboard Credit | View Itinerary | Get FREE Quote | |
25 reviews | 7 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway (Mar 28 2026)) | Mar 28, 2026 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Gustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | Road Bay | Soper's Hole | $2,467 Up To $250 Onboard Credit | View Itinerary | Get FREE Quote | |
25 reviews | 7 night Caribbean (Classic Caribbean (Dec 7 2025)) | Dec 07, 2025 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Mayreau | Philipsburg, St. Maarten | Roseau | $2,551 Up To $300 Onboard Credit | View Itinerary | Get FREE Quote | |
11 reviews  | 7 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway (Jan 31 2026)) | Jan 31, 2026 | Windstar | Wind Spirit | Philipsburg | Philipsburg | 7 Nights | Gustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | Road Bay | Soper's Hole | $2,560 Up To $300 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
11 reviews | 7 night Caribbean (Jewels of Windward Islands (Mar 21 2026)) | Mar 21, 2026 | Windstar | Wind Spirit | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Basseterre | Bridgetown | Les Saintes | Pigeon Island | Roseau | $2,616 Up To $300 Onboard Credit | View Itinerary | Get FREE Quote | |
25 reviews | 7 night Caribbean (Classic Caribbean (Feb 28 2026)) | Feb 28, 2026 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Philipsburg, St. Maarten | Pigeon Island | Roseau | $2,651 Shipboard Credit Per Person ($150) | Shipboard Credit Per Person ($150) | View Itinerary | Get FREE Quote |
11 reviews | 7 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway (Feb 21 2026)) | Feb 21, 2026 | Windstar | Wind Spirit | Philipsburg | Philipsburg | 7 Nights | Gustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | Road Bay | Soper's Hole | $2,660 Up To $300 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
18 reviews  | 7 night Caribbean (San Juan & the Virgin Islands (Dec 13 2026)) | Dec 13, 2026 | Windstar | Star Pride | San Juan | San Juan | 7 Nights | Basseterre | CRUZ BAY, ST. JOHN, Virgin Islands (U.S.) | Gustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | San Juan | $2,662 Up To $300 Onboard Credit | View Itinerary | Get FREE Quote | |
18 reviews | 7 night Caribbean (San Juan & the Virgin Islands (Nov 29 2026)) | Nov 29, 2026 | Windstar | Star Pride | San Juan | San Juan | 7 Nights | Basseterre | CRUZ BAY, ST. JOHN, Virgin Islands (U.S.) | Gustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | San Juan | $2,662 Up To $300 Onboard Credit | Suite! | View Itinerary | Get FREE Quote |
18 reviews | 7 night Caribbean (San Juan & the Virgin Islands (Nov 15 2026)) | Nov 15, 2026 | Windstar | Star Pride | San Juan | San Juan | 7 Nights | Basseterre | CRUZ BAY, ST. JOHN, Virgin Islands (U.S.) | Gustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | San Juan | $2,662 Up To $300 Onboard Credit | View Itinerary | Get FREE Quote | |
25 reviews | 7 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway (Dec 14 2025)) | Dec 14, 2025 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Gustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | Road Bay | Soper's Hole | $2,667 Up To $300 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
25 reviews | 7 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway (Jan 4 2026)) | Jan 04, 2026 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Gustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | Road Bay | Soper's Hole | $2,710 Up To $300 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
11 reviews | 7 night Caribbean (Lush & Lovely Islands of the Lesser Antilles (Feb 28 2026)) | Feb 28, 2026 | Windstar | Wind Spirit | Philipsburg | Bridgetown | 7 Nights | Basseterre | Bridgetown | Gustavia | Les Saintes | Philipsburg, St. Maarten | Pigeon Island | Roseau | $2,720 Up To $300 Onboard Credit | View Itinerary | Get FREE Quote | |
25 reviews | 7 night Caribbean (Jewels of Windward Islands (Jan 18 2026)) | Jan 18, 2026 | Windstar | Wind Surf | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Mayreau | Pigeon Island | St. George's | $2,722 Up To $300 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
18 reviews | 7 night Caribbean (San Juan & the Virgin Islands (Nov 9 2025)) | Nov 09, 2025 | Windstar | Star Pride | San Juan | San Juan | 7 Nights | Bequia | 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 Itinerary | Get FREE Quote |
25 reviews | 7 night Caribbean (Lush & Lovely Islands of the Lesser Antilles (Jan 11 2026)) | Jan 11, 2026 | Windstar | Wind Surf | Philipsburg | Bridgetown | 7 Nights | Basseterre | Bridgetown | Gustavia | Kingstown | Les Saintes | Philipsburg, St. Maarten | Pigeon Island | $2,736 Up To $300 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
11 reviews | 7 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway (Jan 24 2026)) | Jan 24, 2026 | Windstar | Wind Spirit | Philipsburg | Philipsburg | 7 Nights | Gustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | Road Bay | Soper's Hole | $2,760 Up To $300 Onboard Credit | View Itinerary | Get FREE Quote | |
11 reviews | 7 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway (Feb 14 2026)) | Feb 14, 2026 | Windstar | Wind Spirit | Philipsburg | Philipsburg | 7 Nights | Gustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | Road Bay | Soper's Hole | $2,760 Up To $300 Onboard Credit | View Itinerary | Get FREE Quote | |
18 reviews | 7 night Caribbean (San Juan & the Virgin Islands (Nov 16 2025)) | Nov 16, 2025 | Windstar | Star Pride | San Juan | San Juan | 7 Nights | Basseterre | 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 Itinerary | Get FREE Quote |
Departure Ports
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Destinations
- Tahiti Cruises (1162)
- Europe - All Cruises (438)
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- Caribbean - All Cruises (168)
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