Your Caribbean - All Results
Your Caribbean - All Results
Sail Date | Cruise Line | Ship | Destination | Departs | Length | Price | You Save | Discounts | |
---|---|---|---|---|---|---|---|---|---|
24 reviews | Dec 02, 2025 | Windstar | Wind Surf | 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 07, 2025 | Windstar | Wind Surf | 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 | 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 | Mar 21, 2026 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,299 Up To $250 Onboard Credit | Onboard Credit! |
24 reviews | Dec 14, 2025 | Windstar | Wind Surf | 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 | Mar 07, 2026 | Windstar | Wind Surf | 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 Up To $250 Onboard Credit | Onboard Credit! |
24 reviews | Mar 14, 2026 | Windstar | Wind Surf | 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 | Mar 28, 2026 | Windstar | Wind Surf | 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 Up To $250 Onboard Credit | Onboard Credit! |
24 reviews | Jan 04, 2026 | Windstar | Wind Surf | 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 11, 2026 | Windstar | Wind Surf | 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 18, 2026 | Windstar | Wind Surf | 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 04, 2025 | Windstar | Wind Surf | 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 25, 2025 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,599 Up To $300 Onboard Credit | Onboard Credit! |
24 reviews | Feb 22, 2025 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,599 Up To $300 Onboard Credit | |
24 reviews | Mar 22, 2025 | Windstar | Wind Surf | 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! |
24 reviews | Feb 01, 2025 | Windstar | Wind Surf | 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 | |
24 reviews | Feb 15, 2025 | Windstar | Wind Surf | 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 08, 2025 | Windstar | Wind Surf | 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 | 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 | Dec 21, 2025 | Windstar | Wind Surf | 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) |
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