Windstar Cruises from Philipsburg, St. Maarten 2025/2026
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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 | 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 | 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 | 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 | 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 | $5,019 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 28 2025)) | Dec 28, 2025 | Windstar | Wind Surf | Philipsburg | Philipsburg | 6 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | Road Bay | Soper's Hole | $2,967 Up To $300 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
25 reviews | 14 night Star Collector Voyages (Leeward & Windward Caribbean Havens (Jan 4 2026)) | Jan 04, 2026 | Windstar | Wind Surf | Philipsburg | Bridgetown | 14 Nights | Basseterre | Bridgetown | Gustavia | Jost Van Dyke, Great Harbour | Kingstown | Les Saintes | Philipsburg, St. Maarten | Pigeon Island | Road Bay | Soper's Hole | $4,247 Shipboard Credit Per Person ($150) | Shipboard Credit Per Person ($150) | View Itinerary | Get FREE Quote |
25 reviews | 21 night Star Collector Voyages (A Lesser Antilles Odyssey (Jan 4 2026)) | Jan 04, 2026 | Windstar | Wind Surf | Philipsburg | Bridgetown | 21 Nights | Anse Mitan | Basseterre | Bequia | Bridgetown | Castries | Gustavia | Jost Van Dyke, Great Harbour | Kingstown | Les Saintes | Mayreau | Philipsburg, St. Maarten | Pigeon Island | Road Bay | Soper's Hole | St. George's | $6,370 Up To $750 Onboard Credit | View Itinerary | Get FREE Quote | |
25 reviews | 28 night Star Collector Voyages (The Best of the Windward & Leeward Isles (Jan 4 2026)) | Jan 04, 2026 | Windstar | Wind Surf | Philipsburg | Oranjestad | 28 Nights | Anse Mitan | Basseterre | Bequia | Bridgetown | Castries | Gustavia | Jost Van Dyke, Great Harbour | Kingstown | Kralendijk | Les Saintes | Man-O-War Bay | Mayreau | Oranjestad | Philipsburg, St. Maarten | Pigeon Island | Road Bay | Soper's Hole | Soufriere | St. George's | Willemstad | $9,195 Up To $1000 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
25 reviews | 55 night Star Collector Voyages (Grand Caribbean Adventure (Jan 4 2026)) | Jan 04, 2026 | Windstar | Wind Surf | Philipsburg | Philipsburg | 55 Nights | Anse Mitan | Basseterre | Belize City | Bequia | Bocas del Toro | Bridgetown | Cartagena | Castries | Colón | Costa Maya | Cozumel | Grand Cayman | Gustavia | Jost Van Dyke, Great Harbour | Kingstown | Kralendijk | La Romana | Les Saintes | Man-O-War Bay | Mayreau | Oranjestad | Philipsburg, St. Maarten | Pigeon Island | Port Antonio | Road Bay | Roatan | Santa Marta | Santo Domingo | Soper's Hole | Soufriere | St. George's | Willemstad | $19,546 Up To $1000 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
25 reviews | 6 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway (Jan 4 2026)) | Jan 04, 2026 | Windstar | Wind Surf | Philipsburg | Philipsburg | 6 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | Road Bay | Soper's Hole | $2,610 Up To $300 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 | |
25 reviews | 14 night Star Collector Voyages (Antilles Adventures (Jan 11 2026)) | Jan 11, 2026 | Windstar | Wind Surf | Philipsburg | Bridgetown | 14 Nights | Anse Mitan | Basseterre | Bequia | Bridgetown | Castries | Gustavia | Kingstown | Les Saintes | Mayreau | Philipsburg, St. Maarten | Pigeon Island | St. George's | $4,359 Up To $500 Onboard Credit | 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 | $5,994 Up To $750 Onboard Credit | 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 | $4,533 Up To $500 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 | 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 | $4,478 Shipboard Credit Per Person ($150) | Shipboard Credit Per Person ($150) | View Itinerary | Get FREE Quote |
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