11 reviews | Jan 24, 2026 | Windstar | Wind Spirit | Caribbean | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $2,499 Up To $250 Onboard Credit | | Onboard Credit! |
11 reviews | Jan 31, 2026 | Windstar | Wind Spirit | Caribbean | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $2,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Jan 31, 2026 | Windstar | Wind Spirit | 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 | $4,099 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Feb 07, 2026 | Windstar | Wind Spirit | 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 | $4,099 Up To $500 Onboard Credit | | Onboard Credit! |
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11 reviews | Feb 07, 2026 | Windstar | Wind Spirit | Caribbean | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,599 Up To $300 Onboard Credit | | Onboard Credit! |
11 reviews | Feb 14, 2026 | Windstar | Wind Spirit | Caribbean | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $2,599 Up To $300 Onboard Credit | | |
11 reviews | Feb 21, 2026 | Windstar | Wind Spirit | Caribbean | Philipsburg | Bridgetown | 14 Nights | Basseterre | Bridgetown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $3,999 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Feb 21, 2026 | Windstar | Wind Spirit | Caribbean | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $2,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Feb 21, 2026 | Windstar | Wind Spirit | Caribbean | Philipsburg | Bridgetown | 21 Nights | Anse Mitan | Basseterre | Bridgetown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $6,099 Up To $750 Onboard Credit | | Onboard Credit! |
11 reviews | Feb 28, 2026 | Windstar | Wind Spirit | Caribbean | Philipsburg | Bridgetown | 7 Nights | Basseterre | Bridgetown | Gustavia | Les Saintes | Little Bay | Pigeon Island | Roseau | St. Maarten | $2,399 Up To $250 Onboard Credit | | Onboard Credit! |
11 reviews | Feb 28, 2026 | Windstar | Wind Spirit | Caribbean | Philipsburg | Bridgetown | 14 Nights | Anse Mitan | Basseterre | Bridgetown | Gustavia | Les Saintes | Little Bay | Pigeon Island | Roseau | St. Maarten | $3,999 Up To $500 Onboard Credit | | Onboard Credit! |
24 reviews | Feb 28, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,299 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Feb 28, 2026 | 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 | $3,699 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Mar 07, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $2,399 Up To $250 Onboard Credit | | Onboard Credit! |
24 reviews | Mar 14, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $2,399 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Mar 14, 2026 | 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 | $3,699 Up To $500 Onboard Credit | | Onboard Credit! |
24 reviews | Mar 21, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,299 Up To $250 Onboard Credit | | Onboard Credit! |
24 reviews | Mar 21, 2026 | 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 | $3,699 Up To $500 Onboard Credit | | |
24 reviews | Mar 28, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $2,399 Up To $250 Onboard Credit | | |
24 reviews | Dec 21, 2024 | 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 | $5,399 Up To $750 Onboard Credit | | Onboard Credit! |