24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | 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 ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | 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 ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | 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 ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | 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 |
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24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | 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 ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | 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! |
![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/197__202302081343__.jpg.webp) | Apr 09, 2025 | SeaDream Yacht Club | SeaDream I | Caribbean | Philipsburg | Philipsburg | 5 Nights | Falmouth Bay, Antigua and Barbuda | Gustavia, St. Barths, F.W.I. | Philipsburg, Sint Maarten, Dutch Caribbean | White Bay, Jost van Dyke, B. V. I. | $3,099 Up To $500 Onboard Credit | | Onboard Credit! |
![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/197__202302081343__.jpg.webp) | Apr 14, 2025 | SeaDream Yacht Club | SeaDream I | Caribbean | Philipsburg | Philipsburg | 5 Nights | Gustavia, St. Barths, F.W.I. | Norman Island, B. V. I. | Philipsburg, Sint Maarten, Dutch Caribbean | Spanish Town, Virgin Gorda, B. V. I. | White Bay, Jost van Dyke, B. V. I. | $3,099 Up To $500 Onboard Credit | | Onboard Credit! |
24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | 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 ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | 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 ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | 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) |
24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | Feb 28, 2026 | 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) |
24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | Mar 14, 2026 | 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 Up To $500 Onboard Credit | | |
24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | Mar 21, 2026 | 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 Up To $500 Onboard Credit | | |
24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | 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) |
![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/197__202302081343__.jpg.webp) | Dec 20, 2025 | SeaDream Yacht Club | SeaDream I | Caribbean | Philipsburg | San Juan del Sur | 7 Nights | Charlestown, Nevis, St. Kitts & Nevis | Gustavia, St. Barths, F.W.I. | Philipsburg, Sint Maarten, Dutch Caribbean | Prickly Pear, B.V.I, B. V. I. | San Juan, Puerto Rico | Sandy Ground, Anguilla,B.W.I. | $3,999 Up To $500 Onboard Credit | | Onboard Credit! |
![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/197__202302081343__.jpg.webp) | Jan 25, 2025 | SeaDream Yacht Club | SeaDream I | Caribbean | Philipsburg | White Bay | -1 Nights | Bridgetown, Barbados | Gustavia, St. Barths, F.W.I. | Norman Island, B. V. I. | Philipsburg, Sint Maarten, Dutch Caribbean | Port Elizabeth, Bequia, St. Vincent and the Grenadines | Soper's Hole, Tortola, B. V. I. | Terre De Haut, Îles des Saintes, Guadeloupe, F.W.I. | Tobago Cays, St. Vincent and the Grenadines | White Bay, Jost van Dyke, B. V. I. | $3,999 Up To $500 Onboard Credit | | Onboard Credit! |
24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | 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) |
11 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/120.jpg.webp) | Feb 21, 2026 | Windstar | Wind Spirit | Caribbean | Philipsburg | Bridgetown | 14 Nights | Basseterre | Bridgetown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | 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) |
![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/197__202302081343__.jpg.webp) | Apr 13, 2025 | SeaDream Yacht Club | SeaDream I | Caribbean | Philipsburg | Philipsburg | 6 Nights | Gustavia, St. Barths, F.W.I. | Norman Island, B. V. I. | Philipsburg, Sint Maarten, Dutch Caribbean | Sandy Ground, Anguilla,B.W.I. | Spanish Town, Virgin Gorda, B. V. I. | White Bay, Jost van Dyke, B. V. I. | $4,099 Up To $500 Onboard Credit | | Onboard Credit! |