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  | 7 night Caribbean (San Juan & the Virgin Islands (Oct 26 2025)) | Oct 26, 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 Up To $300 Onboard Credit | Suite! | View Itinerary | Get FREE Quote |
17 reviews | 7 night Caribbean (San Juan & the Virgin Islands (Nov 2 2025)) | Nov 02, 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 | $2,962 Up To $300 Onboard Credit | Suite! | View Itinerary | Get FREE Quote |
17 reviews | 14 night Star Collector Voyages (Lovely Leewards (Nov 2 2025)) | Nov 02, 2025 | Windstar | Star Pride | San Juan | San Juan | 14 Nights | Basseterre | 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 | View Itinerary | Get FREE Quote | |
17 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 |
17 reviews | 14 night Star Collector Voyages (Lovely Leewards (Nov 9 2025)) | Nov 09, 2025 | Windstar | Star Pride | San Juan | San Juan | 14 Nights | Basseterre | 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 Itinerary | Get FREE Quote |
17 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 |
17 reviews | 14 night Star Collector Voyages (Lovely Leewards (Nov 16 2025)) | Nov 16, 2025 | Windstar | Star Pride | San Juan | San Juan | 14 Nights | Basseterre | 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 Itinerary | Get FREE Quote |
25 reviews  | 19 night Star Collector Voyages (Hearty Ports & Rum Punches - A Transatlantic Crossing (Nov 18 2025)) | Nov 18, 2025 | Windstar | Wind Surf | Lisbon | Philipsburg | 19 Nights | Gustavia | 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 Itinerary | Get FREE Quote |
17 reviews | 14 night Star Collector Voyages (Lovely Leewards (Nov 23 2025)) | Nov 23, 2025 | Windstar | Star Pride | San Juan | San Juan | 14 Nights | Basseterre | 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 Itinerary | Get FREE Quote |
17 reviews | 7 night Caribbean (San Juan & the Virgin Islands (Nov 30 2025)) | Nov 30, 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 |
17 reviews | 13 night Star Collector Voyages (Star Collector: Beaches & Bastions of the BVI and Spanish Caribbean (Nov 30 2025)) | Nov 30, 2025 | Windstar | Star Pride | San Juan | Colon | 13 Nights | Basseterre | 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 | View Itinerary | Get FREE Quote | |
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 | 12 night Star Collector Voyages (Ivory Beaches & Sapphire Seas of the Caribbean (Dec 2 2025)) | Dec 02, 2025 | Windstar | Wind Surf | Philipsburg | Philipsburg | 12 Nights | Basseterre | Charlestown | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Mayreau | Philipsburg, St. Maarten | Roseau | Soper's Hole | $3,502 Up To $500 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 | $2,351 Up To $250 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
25 reviews | 14 night Star Collector Voyages (Caribbean Explorations (Dec 7 2025)) | Dec 07, 2025 | Windstar | Wind Surf | Philipsburg | Philipsburg | 14 Nights | Basseterre | 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 | View Itinerary | Get FREE Quote | |
17 reviews | 13 night Star Collector Voyages (Star Collector: Coffee, Canal & Callaloo - Central America, Columbia & the Caribbean (Dec 7 2025)) | Dec 07, 2025 | Windstar | Star Pride | San Juan | Puerto Caldera | 13 Nights | Balboa / 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 | View Itinerary | Get FREE Quote | |
25 reviews | 14 night Star Collector Voyages (Caribbean Explorations (Dec 14 2025)) | Dec 14, 2025 | Windstar | Wind Surf | Philipsburg | Philipsburg | 14 Nights | Basseterre | 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 Itinerary | Get FREE Quote |
25 reviews | 6 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway (Dec 14 2025)) | Dec 14, 2025 | Windstar | Wind Surf | Philipsburg | Philipsburg | 6 Nights | Falmouth 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 Itinerary | Get FREE Quote |
25 reviews | 7 night Caribbean (Classic Caribbean (Dec 21 2025)) | Dec 21, 2025 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Mayreau | Philipsburg, St. Maarten | Roseau | $2,951 Shipboard Credit Per Person ($150) | Shipboard Credit Per Person ($150) | View Itinerary | Get FREE Quote |
25 reviews | 14 night Star Collector Voyages (Caribbean Explorations (Dec 21 2025)) | Dec 21, 2025 | Windstar | Wind Surf | Philipsburg | Philipsburg | 14 Nights | Basseterre | 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 Itinerary | Get FREE Quote |
Departure Ports
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Destinations
- Tahiti Cruises (1258)
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