15 reviews | Nov 03, 2024 | Windstar | Star Pride | Caribbean - Eastern | San Juan | San Juan | 6 Nights | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | San Juan | St. Maarten | Virgin Gorda | $2,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
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 | | |
15 reviews | Nov 09, 2024 | Windstar | Star Pride | Caribbean - Eastern | San Juan | San Juan | 7 Nights | Bequia | Les Saintes | Pigeon Island | San Juan | St. George's | St. Maarten | $3,199 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Nov 16, 2024 | Windstar | Star Pride | Caribbean - Eastern | San Juan | San Juan | 7 Nights | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | San Juan | St. Maarten | St. Thomas | Virgin Gorda | $2,399 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
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15 reviews | Nov 23, 2024 | Windstar | Star Pride | Caribbean - Eastern | San Juan | San Juan | 7 Nights | Bequia | Les Saintes | Pigeon Island | San Juan | St. George's | St. Maarten | $2,599 Up To $300 Onboard Credit | | Suite! |
15 reviews | Nov 30, 2024 | Windstar | Star Pride | Caribbean - Eastern | San Juan | San Juan | 7 Nights | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | San Juan | St. Maarten | St. Thomas | Virgin Gorda | $2,999 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Dec 07, 2024 | Windstar | Star Pride | Caribbean - Eastern | San Juan | Bridgetown | 7 Nights | Bridgetown | Gustavia | Little Bay | Pigeon Island | Roseau | San Juan | St. George's | St. Thomas | $2,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Dec 21, 2024 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,999 Up To $300 Onboard Credit | | Onboard Credit! |
24 reviews | Dec 28, 2024 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda | $3,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Jan 04, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Jan 11, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda | $2,799 Up To $300 Onboard Credit | | |
24 reviews | Jan 18, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,799 Up To $300 Onboard Credit Welcome Reception Exclusive Amenity Distinctive Host | | *Distinctive Voyage |
24 reviews | Jan 25, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,599 Up To $300 Onboard Credit | | |
24 reviews | Feb 01, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda | $2,699 Up To $300 Onboard Credit | | Onboard Credit! |
24 reviews | Feb 08, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,899 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Feb 15, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda | $2,699 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Feb 22, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,599 Up To $300 Onboard Credit | | |
24 reviews | Mar 08, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda | $2,699 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Mar 15, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,699 Up To $300 Onboard Credit Welcome Reception Exclusive Amenity Distinctive Host | | *Distinctive Voyage |
24 reviews | Mar 22, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda | $2,599 Up To $300 Onboard Credit | | Onboard Credit! |