24 reviews | Dec 02, 2025 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 5 Nights | Gustavia | Jost Van Dyke, Great Harbour | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $1,999 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Dec 02, 2025 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 12 Nights | Basseterre | Charlestown | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Roseau | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $3,399 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Dec 07, 2025 | 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 | 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) |
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15 reviews | Dec 07, 2025 | Windstar | Star Pride | Caribbean | San Juan | Colon | 6 Nights | Cartagena | Colón | San Blas | San Juan | Santo Domingo | $2,899 Up To $300 Onboard Credit | | Suite! |
24 reviews | Dec 14, 2025 | 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 | $2,399 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Dec 14, 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 | $3,999 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Dec 21, 2025 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,699 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Dec 21, 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 | $4,299 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Dec 28, 2025 | 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 | $2,699 Up To $300 Onboard Credit | | Onboard Credit! |
10 reviews | Dec 10, 2025 | 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 | Dec 20, 2025 | 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 | $3,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
10 reviews | Dec 30, 2025 | 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 | $3,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Dec 06, 2025 | Windstar | Wind Spirit | Panama Canal | Puerto Caldera | Colon | 7 Nights | Balboa / Fuerte Amador | Colón | Golfo Dulce | Isla Parida | Panama Canal | Puerto Caldera | Quepos | $2,599 Up To $300 Onboard Credit | | Onboard Credit! |
15 reviews | Dec 13, 2025 | Windstar | Star Pride | Panama Canal | Colon | Puerto Caldera | 7 Nights | Balboa / Fuerte Amador | Colón | Golfo Dulce | Isla Parida | Panama Canal | Puerto Caldera | Quepos | $2,699 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Dec 20, 2025 | 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) |
15 reviews | Dec 20, 2025 | Windstar | Star Pride | Panama Canal | Puerto Caldera | Lima | 18 Nights | Balboa / Fuerte Amador | Colón | Golfo Dulce | Guayaquil, Ecuador | Isla Parida | Lima, Peru | Manta, Equador | Panama Canal | Puerto Caldera | Quepos | Trujillo, Peru | $6,699 Up To $750 Onboard Credit | | |
15 reviews | Dec 27, 2025 | Windstar | Star Pride | Panama Canal | Colon | Lima | 11 Nights | Colón | Guayaquil, Ecuador | Lima, Peru | Manta, Equador | Panama Canal | Trujillo, Peru | $5,299 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
2 reviews | Dec 04, 2025 | Windstar | Star Breeze | Tahiti | Papeete | Papeete | 7 Nights | Bora Bora | Huahine | Moorea | Motu Mahaea (Tahaa) | Papeete | Raiatea | $3,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
2 reviews | Dec 11, 2025 | Windstar | Star Breeze | Tahiti | Papeete | Papeete | 7 Nights | Bora Bora | Huahine | Moorea | Motu Mahaea (Tahaa) | Papeete | Raiatea | $3,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |