24 reviews | Mar 30, 2024 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Lisbon | 14 Nights | Lisbon | Ponta Delgada | St. Maarten | $1,399 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
10 reviews | Nov 05, 2024 | Windstar | Wind Star | Transatlantic | Lisbon | Bridgetown | 14 Nights | Bridgetown | Lisbon | $2,199 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Feb 22, 2025 | Windstar | Wind Spirit | Transatlantic | Bridgetown | Lisbon | 15 Nights | Bridgetown | Lisbon | $2,399 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
10 reviews | Mar 26, 2025 | Windstar | Wind Star | Transatlantic | Bridgetown | Lisbon | 15 Nights | Bridgetown | Lisbon | $2,399 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
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11 reviews | Nov 13, 2024 | Windstar | Wind Spirit | Transatlantic | Lisbon | Bridgetown | 14 Nights | Bridgetown | Lisbon | $2,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Mar 29, 2025 | Windstar | Wind Surf | Europe | Philipsburg | Lisbon | 14 Nights | Lisbon | Ponta Delgada | St. Maarten | $2,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Nov 04, 2025 | Windstar | Wind Spirit | Transatlantic | Lisbon | Bridgetown | 14 Nights | Bridgetown | Lisbon | $2,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
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 | $3,499 Up To $500 Onboard Credit | | Onboard Credit! |
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 | $3,499 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 | $3,699 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
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 | $3,699 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Dec 07, 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 | $3,699 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 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 | 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! |
11 reviews | Jan 25, 2025 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 14 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Kingstown | Les Saintes | Little Bay | Mayreau | Pigeon Island | Roseau | St. George's | The Pitons | $3,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Feb 01, 2025 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 14 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Kingstown | Les Saintes | Little Bay | Mayreau | Pigeon Island | Roseau | St. George's | The Pitons | $3,799 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 | $3,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Jan 04, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Bridgetown | 14 Nights | Basseterre | Bridgetown | Deshaies | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $3,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Jan 04, 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 | $3,899 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |