11 reviews | Jan 04, 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 | $3,999 Up To $500 Onboard Credit | | |
11 reviews | Jan 18, 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 | $3,999 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Mar 08, 2025 | Windstar | Star Pride | World Cruise | Balboa | Bridgetown | 14 Nights | Balboa / Fuerte Amador | Bocas del Toro | Bridgetown | Cartagena | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | Panama Canal | San Blas | Santa Marta | Soufriere | Willemstad | $3,999 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Jan 11, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Bridgetown | 14 Nights | Anse Mitan | Basseterre | Bequia | Bridgetown | Castries | Deshaies | Gustavia | Little Bay | Mayreau | Pigeon Island | Roseau | St. George's | St. Maarten | $3,999 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
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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! |
11 reviews | Dec 28, 2024 | 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 | $4,099 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Jan 11, 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 | $4,099 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Jan 18, 2026 | Windstar | Wind Surf | Caribbean | Bridgetown | Oranjestad | 14 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | Pigeon Island | Soufriere | St. George's | Willemstad | $4,099 Up To $500 Onboard Credit | | Onboard Credit! |
11 reviews | Mar 07, 2026 | 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 | $4,099 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Mar 14, 2026 | 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 | $4,099 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Dec 14, 2024 | 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 | $4,299 Up To $500 Onboard Credit | | |
15 reviews | Nov 09, 2024 | Windstar | Star Pride | Caribbean | San Juan | San Juan | 14 Nights | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | St. Thomas | Virgin Gorda / Prickly Pear | $4,399 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Dec 21, 2024 | 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 | $4,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
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 | $4,499 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 | $4,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Feb 08, 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 | $4,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Jan 25, 2026 | Windstar | Wind Surf | World Cruise | Bridgetown | Colon | 15 Nights | Bocas del Toro | Bridgetown | Cartagena | Colón | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | Santa Marta | Soufriere | Willemstad | $4,699 Up To $500 Onboard Credit | | Onboard Credit! |
11 reviews | Jan 14, 2026 | Windstar | Wind Spirit | Caribbean | Philipsburg | Philipsburg | 17 Nights | Anse Mitan | Bequia | Castries | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Mayreau | Road Bay | Roseau | Soper's Hole | St. George's | St. Maarten | Virgin Gorda / Prickly Pear | $4,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Feb 17, 2026 | Windstar | Wind Surf | Caribbean | Cozumel | Philipsburg | 18 Nights | Basseterre | Cayman Brac | Charlestown | Cozumel | Grand Cayman | Gustavia | Jost Van Dyke, Great Harbour | La Romana | Les Saintes | Pigeon Island | Port Antonio | Roseau | Santo Domingo | St. Maarten | Virgin Gorda / Prickly Pear | $4,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
10 reviews | Dec 03, 2024 | Windstar | Wind Star | Caribbean | Puerto Caldera | Colon | 11 Nights | Balboa / Fuerte Amador | Colón | Golfo Dulce | Isla Parida | La Fortuna (Arenal), Costa Rica | Panama Canal | Puerto Caldera | Quepos | San Jose | Santa Elena (Monteverde) | $4,899 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |