24 reviews | Jan 18, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,799 Up To $300 Onboard Credit Welcome Reception Exclusive Amenity Distinctive Host | | *Distinctive Voyage |
24 reviews | Jan 18, 2025 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $4,599 Up To $500 Onboard Credit | | Onboard Credit! |
24 reviews | Jan 25, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,599 Up To $300 Onboard Credit | | Onboard Credit! |
24 reviews | Feb 01, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda | $4,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
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24 reviews | Feb 01, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda | $2,599 Up To $300 Onboard Credit | | Onboard Credit! |
24 reviews | Feb 08, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda | $4,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Feb 08, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Feb 15, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda | $4,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Feb 15, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda | $2,699 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Feb 22, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,599 Up To $300 Onboard Credit | | Onboard Credit! |
24 reviews | Feb 22, 2025 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $4,399 Up To $500 Onboard Credit | | Onboard Credit! |
24 reviews | Mar 08, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda | $4,199 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Mar 08, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda | $2,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Mar 15, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda | $4,199 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Mar 15, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,699 Up To $300 Onboard Credit Welcome Reception Exclusive Amenity Distinctive Host | | *Distinctive Voyage |
24 reviews | Mar 22, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda | $2,599 Up To $300 Onboard Credit | | Onboard Credit! |
15 reviews | Oct 26, 2025 | Windstar | Star Pride | Caribbean | San Juan | San Juan | 7 Nights | Basseterre | Gustavia | Jost Van Dyke, Great Harbour | San Juan | St. Maarten | Virgin Gorda / Prickly Pear | $2,699 Up To $300 Onboard Credit | | Suite! |
15 reviews | Nov 02, 2025 | Windstar | Star Pride | Caribbean | San Juan | San Juan | 7 Nights | Basseterre | Gustavia | Jost Van Dyke, Great Harbour | San Juan | St. Maarten | Virgin Gorda / Prickly Pear | $2,699 Up To $300 Onboard Credit | | Suite! |
15 reviews | Nov 16, 2025 | Windstar | Star Pride | Caribbean | San Juan | San Juan | 7 Nights | Basseterre | Gustavia | Jost Van Dyke, Great Harbour | San Juan | St. Maarten | Virgin Gorda / Prickly Pear | $2,699 Up To $300 Onboard Credit | | Suite! |
24 reviews | Nov 18, 2025 | Windstar | Wind Surf | Transatlantic | Lisbon | Philipsburg | 19 Nights | Gustavia | Jost Van Dyke, Great Harbour | Lisbon | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $3,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |