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 | ||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|
11 reviews  | 22 night Star Collector Voyages (Caribbean Beats & Transatlantic Treats (Mar 21 2026)) | Mar 21, 2026 | Windstar | Wind Spirit | Bridgetown | Lisbon | 22 Nights | Anse Mitan | Basseterre | Bridgetown | Les Saintes | Lisbon | Pigeon Island | Roseau | $4,142 Up To $500 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 (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 |
11 reviews | 7 night Caribbean (Windward Island Delights (Dec 28 2025)) | Dec 28, 2025 | Windstar | Wind Spirit | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Basseterre | Bridgetown | Les Saintes | Pigeon Island | Roseau | $3,216 Shipboard Credit Per Person ($150) | Shipboard Credit Per Person ($150) | View Itinerary | Get FREE Quote |
11 reviews | 14 night Star Collector Voyages (Captivating Caribbean (Mar 7 2026)) | Mar 07, 2026 | Windstar | Wind Spirit | Bridgetown | Bridgetown | 14 Nights | Basseterre | Bequia | Bridgetown | Castries | Kingstown | Les Saintes | Mayreau | Pigeon Island | Roseau | St. George's | The Pitons | $4,133 Shipboard Credit Per Person ($150) | Shipboard Credit Per Person ($150) | View Itinerary | Get FREE Quote |
25 reviews | 15 night Star Collector Voyages (Windward Islands & Spanish New World (Jan 25 2026)) | Jan 25, 2026 | Windstar | Wind Surf | Bridgetown | Colon | 15 Nights | Bocas del Toro | Bridgetown | Cartagena | Colón | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | Santa Marta | Soufriere | Willemstad | $5,366 Up To $750 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
25 reviews | 19 night Star Collector Voyages (Caribbean Cultures: Latin America & the Greater Antilles (Feb 9 2026)) | Feb 09, 2026 | Windstar | Wind Surf | Colon | Philipsburg | 19 Nights | Belize City | Bocas del Toro | Colón | Costa Maya | Cozumel | Grand Cayman | Jost Van Dyke, Great Harbour | La Romana | Philipsburg, St. Maarten | Port Antonio | Roatan | Santo Domingo | $6,208 Up To $750 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
25 reviews | 18 night Star Collector Voyages (Deep Dive into the Blue: Underwater Worlds of the Caribbean (Feb 17 2026)) | Feb 17, 2026 | Windstar | Wind Surf | Cozumel | Philipsburg | 18 Nights | Basseterre | Charlestown | Cozumel | Grand Cayman | Gustavia | Jost Van Dyke, Great Harbour | La Romana | Les Saintes | Philipsburg, St. Maarten | Pigeon Island | Port Antonio | Roseau | Santo Domingo | $5,715 Up To $750 Onboard Credit | Onboard Credit! | 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 |
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 |
11 reviews | 14 night Star Collector Voyages (Caribbean Explorations (Feb 7 2026)) | Feb 07, 2026 | Windstar | Wind Spirit | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Philipsburg, St. Maarten | Pigeon Island | Road Bay | Roseau | Soper's Hole | $5,378 Up To $750 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
11 reviews | 28 night Star Collector Voyages (Star Collector: Grand Caribbean & Panamanian Adventure (Feb 21 2026)) | Feb 21, 2026 | Windstar | Wind Spirit | Philipsburg | Bridgetown | 28 Nights | Anse Mitan | Basseterre | Bequia | Bridgetown | Castries | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Mayreau | Philipsburg, St. Maarten | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. John's | The Pitons | Tobago Cays | $8,415 Up To $1000 Onboard Credit | View Itinerary | Get FREE Quote | |
11 reviews | 22 night Star Collector Voyages (Star Collector: A Lesser Antilles Odyssey (Feb 21 2026)) | Feb 21, 2026 | Windstar | Wind Spirit | Philipsburg | Bridgetown | 22 Nights | Anse Mitan | Basseterre | Bridgetown | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Mayreau | Philipsburg, St. Maarten | Road Bay | Roseau | Soper's Hole | St. John's | $6,898 Up To $750 Onboard Credit | View Itinerary | Get FREE Quote | |
11 reviews | 14 night Star Collector Voyages (Caribbean Explorations (Jan 31 2026)) | Jan 31, 2026 | Windstar | Wind Spirit | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Philipsburg, St. Maarten | Pigeon Island | Road Bay | Roseau | Soper's Hole | $5,178 Shipboard Credit Per Person ($150) | Shipboard Credit Per Person ($150) | 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 (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 | |
25 reviews | 22 night Star Collector Voyages (Atlantic Interludes & Iberian Indulgences (Apr 4 2026)) | Apr 04, 2026 | Windstar | Wind Surf | Philipsburg | Barcelona | 22 Nights | Almeria, Spain | Barcelona | Cádiz | Cartagena | Gibraltar | Lisbon | Málaga | Palma de Mallorca | Philipsburg, St. Maarten | Ponta Delgada | $5,388 Shipboard Credit Per Person ($150) | Shipboard Credit Per Person ($150) | View Itinerary | Get FREE Quote |
11 reviews | 10 night Caribbean (Blue Waters of the Leeward Islands (Jan 14 2026)) | Jan 14, 2026 | Windstar | Wind Spirit | Philipsburg | Philipsburg | 10 Nights | Anse Mitan | Basseterre | Castries | Charlestown | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Philipsburg, St. Maarten | Roseau | $4,333 Up To $500 Onboard Credit | View Itinerary | Get FREE Quote | |
11 reviews | 17 night Star Collector Voyages (A Leeward Island Loop (Jan 14 2026)) | Jan 14, 2026 | Windstar | Wind Spirit | Philipsburg | Philipsburg | 17 Nights | Anse Mitan | Basseterre | Castries | Charlestown | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Philipsburg, St. Maarten | Road Bay | Roseau | Soper's Hole | $6,394 Up To $750 Onboard Credit | Onboard Credit! | 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 | View Itinerary | Get FREE Quote | |
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