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! |
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 | | |
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! |
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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! |
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! |
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) |