15 reviews | Jan 03, 2026 | Windstar | Star Pride | Galapagos | Lima | Colon | 15 Nights | Colón | Guayaquil, Ecuador | Lima, Peru | Manta, Equador | Panama Canal | Trujillo, Peru | $7,999 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Jan 04, 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 | $2,499 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, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Bridgetown | 21 Nights | Anse Mitan | Basseterre | Bequia | Bridgetown | Castries | Deshaies | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | Mayreau | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. George's | St. Maarten | Virgin Gorda / Prickly Pear | $5,999 Up To $750 Onboard Credit | | Onboard Credit! |
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24 reviews | Jan 04, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 55 Nights | Anse Mitan | Basseterre | Belize City | Bequia | Bocas del Toro | Bridgetown | Cartagena | Castries | Cayman Brac | Colón | Costa Maya | Cozumel | Deshaies | Falmouth Harbour | Grand Cayman | Gustavia | Isla San Andres | Jost Van Dyke, Great Harbour | Kralendijk | La Romana | Little Bay | Man-O-War Bay | Mayreau | Oranjestad | Pigeon Island | Port Antonio | Road Bay | Roatan | Roseau | Santa Marta | Santo Domingo | Soper's Hole | Soufriere | St. George's | St. Maarten | Virgin Gorda / Prickly Pear | Willemstad | $15,599 Up To $1000 Onboard Credit | | Onboard Credit! |
24 reviews | Jan 04, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Oranjestad | 28 Nights | Anse Mitan | Basseterre | Bequia | Bridgetown | Castries | Deshaies | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Kralendijk | Little Bay | Man-O-War Bay | Mayreau | Oranjestad | Pigeon Island | Road Bay | Roseau | Soper's Hole | Soufriere | St. George's | St. Maarten | Virgin Gorda / Prickly Pear | Willemstad | $7,899 Up To $1000 Onboard Credit | | Onboard Credit! |
15 reviews | Jan 07, 2026 | Windstar | Star Pride | Panama Canal | Lima | Colon | 11 Nights | Colón | Guayaquil, Ecuador | Lima, Peru | Manta, Equador | Panama Canal | Trujillo, Peru | $4,999 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
2 reviews | Jan 08, 2026 | Windstar | Star Breeze | Tahiti | Papeete | Papeete | 7 Nights | Bora Bora | Huahine | Moorea | Motu Mahaea (Tahaa) | Papeete | Raiatea | $2,999 Up To $300 Onboard Credit | | Suite! |
2 reviews | Jan 08, 2026 | Windstar | Star Breeze | Tahiti | Papeete | Papeete | 10 Nights | Bora Bora | Huahine | Moorea | Motu Mahaea (Tahaa) | Papeete | Raiatea | $4,999 Up To $750 Onboard Credit | | |
10 reviews | Jan 09, 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 | $3,899 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Jan 11, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Bridgetown | 7 Nights | Basseterre | Bridgetown | Deshaies | Gustavia | Little Bay | Pigeon Island | Roseau | St. Maarten | $2,499 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) |
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) |
11 reviews | Jan 14, 2026 | Windstar | Wind Spirit | Caribbean | Philipsburg | Philipsburg | 10 Nights | Anse Mitan | Bequia | Castries | Gustavia | Les Saintes | Little Bay | Mayreau | Roseau | St. George's | St. Maarten | $3,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Jan 18, 2026 | Windstar | Star Pride | Panama Canal | Colon | Lima | 11 Nights | Colón | Guayaquil, Ecuador | Lima, Peru | Manta, Equador | Panama Canal | Trujillo, Peru | $4,999 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Jan 18, 2026 | Windstar | Wind Surf | Caribbean | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Mayreau | Pigeon Island | St. George's | $2,499 Up To $250 Onboard Credit | | Onboard Credit! |
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! |
15 reviews | Jan 18, 2026 | Windstar | Star Pride | Galapagos | Colon | Lima | 15 Nights | Colón | Guayaquil, Ecuador | Lima, Peru | Manta, Equador | Panama Canal | Trujillo, Peru | $7,999 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
10 reviews | Jan 19, 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) |
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! |