24 reviews | Feb 01, 2026 | Windstar | Wind Surf | Caribbean | Oranjestad | Colon | 8 Nights | Bocas del Toro | Cartagena | Colón | Oranjestad | Santa Marta | $3,199 Up To $500 Onboard Credit | | |
24 reviews | Feb 01, 2026 | Windstar | Wind Surf | Caribbean | Oranjestad | Cozumel | 16 Nights | Belize City | Bocas del Toro | Cartagena | Colón | Costa Maya | Cozumel | Isla San Andres | Oranjestad | Roatan | Santa Marta | $5,099 Up To $750 Onboard Credit | | Onboard Credit! |
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 | | |
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! |
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24 reviews | Feb 09, 2026 | Windstar | Wind Surf | Caribbean | Colon | Philipsburg | 19 Nights | Belize City | Bocas del Toro | Cayman Brac | Colón | Costa Maya | Cozumel | Grand Cayman | Isla San Andres | Jost Van Dyke, Great Harbour | La Romana | Port Antonio | Roatan | Santo Domingo | St. Maarten | Virgin Gorda / Prickly Pear | $5,599 Up To $750 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 | | Onboard Credit! |
24 reviews | Feb 17, 2026 | Windstar | Wind Surf | Caribbean | Cozumel | Philipsburg | 11 Nights | Cayman Brac | Cozumel | Grand Cayman | Jost Van Dyke, Great Harbour | La Romana | Port Antonio | Santo Domingo | St. Maarten | Virgin Gorda / Prickly Pear | $3,799 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) |
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 | | |
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 | | |
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) |
10 reviews | Feb 08, 2026 | Windstar | Wind Star | Europe - Western | Santa Cruz De Tenerife | Santa Cruz De Tenerife | 10 Nights | Funchal | Lanzarote | Las Palmas | San Sebastian | Santa Cruz de Palma | Santa Cruz de Tenerife | $3,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
10 reviews | Feb 18, 2026 | Windstar | Wind Star | Europe - Western | Santa Cruz De Tenerife | Santa Cruz De Tenerife | 10 Nights | Funchal | Lanzarote | Las Palmas | San Sebastian | Santa Cruz de Palma | Santa Cruz de Tenerife | $3,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Feb 09, 2026 | Windstar | Wind Surf | Mexico | Colon | Cozumel | 8 Nights | Belize City | Bocas del Toro | Colón | Costa Maya | Cozumel | Isla San Andres | Roatan | $3,199 Up To $500 Onboard Credit | | Onboard Credit! |
15 reviews | Feb 09, 2026 | Windstar | Star Pride | Panama Canal | Colon | Puerto Caldera | 7 Nights | Balboa / Fuerte Amador | Colón | Golfo Dulce | Isla Parida | Panama Canal | Puerto Caldera | Quepos | $3,099 Up To $500 Onboard Credit | | |
15 reviews | Feb 16, 2026 | Windstar | Star Pride | Panama Canal | Puerto Caldera | Colon | 7 Nights | Balboa / Fuerte Amador | Colón | Golfo Dulce | Isla Parida | Panama Canal | Puerto Caldera | Quepos | $3,099 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |