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) | View Itinerary | Get FREE Quote |
11 reviews | 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) | View Itinerary | Get FREE Quote |
11 reviews | Feb 28, 2026 | Windstar | Wind Spirit | Caribbean | Philipsburg | Bridgetown | 14 Nights | Anse Mitan | Basseterre | Bridgetown | Gustavia | Les Saintes | Little Bay | Pigeon Island | Roseau | St. Maarten | $3,999 Up To $500 Onboard Credit | | Onboard Credit! | View Itinerary | Get FREE Quote |
| 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! | View Itinerary | Get FREE Quote |
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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 | $4,099 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
11 reviews | Jan 31, 2026 | Windstar | Wind Spirit | 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 | $4,099 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
11 reviews | Feb 07, 2026 | Windstar | Wind Spirit | 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 | $4,099 Up To $500 Onboard Credit | | Onboard Credit! | View Itinerary | Get FREE Quote |
9 reviews | Jan 25, 2025 | Seabourn | Ovation | Caribbean | Philipsburg | Bridgetown | 7 Nights | Bridgetown, Barbados | Fort-De-France, Martinique | Philipsburg, St. Maarten | Port Elizabeth, Bequia | $4,016 Up To $500 Onboard Credit Welcome Reception Exclusive Amenity Distinctive Host | | *Distinctive Voyage | View Itinerary | Get FREE Quote |
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 | $4,199 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
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) | View Itinerary | Get FREE Quote |
9 reviews | Feb 22, 2025 | Seabourn | Ovation | Caribbean | Philipsburg | Bridgetown | 7 Nights | Bridgetown, Barbados | Fort-De-France, Martinique | Philipsburg, St. Maarten | Port Elizabeth, Bequia | $4,179 Up To $500 Onboard Credit Welcome Reception Exclusive Amenity Distinctive Host | | *Distinctive Voyage | View Itinerary | Get FREE Quote |
9 reviews | Mar 08, 2025 | Seabourn | Ovation | Caribbean | Philipsburg | Bridgetown | 7 Nights | Bridgetown, Barbados | Fort-De-France, Martinique | Philipsburg, St. Maarten | Port Elizabeth, Bequia | $4,179 Up To $500 Onboard Credit Welcome Reception Exclusive Amenity Distinctive Host | | *Distinctive Voyage | View Itinerary | Get FREE Quote |
| Dec 14, 2024 | SeaDream Yacht Club | SeaDream I | Caribbean | Philipsburg | Philipsburg | 7 Nights | Gustavia, St. Barths, F.W.I. | Norman Island, B. V. I. | Philipsburg, Sint Maarten, Dutch Caribbean | Prickly Pear, B.V.I, B. V. I. | Saba, Netherlands Antilles | Sandy Ground, Anguilla,B.W.I. | Soper's Hole, Tortola, B. V. I. | Spanish Town, Virgin Gorda, B. V. I. | $4,391 Up To $500 Onboard Credit | | Onboard Credit! | View Itinerary | Get FREE Quote |
| Jan 04, 2025 | SeaDream Yacht Club | SeaDream I | Caribbean | Philipsburg | Bridgetown | 7 Nights | Bridgetown, Barbados, Barbados | Gustavia, St. Barths, F.W.I. | Mayreau, St. Vincent and the Grenadines | Philipsburg, Sint Maarten, Dutch Caribbean | Rodney Bay, Saint Lucia | Sandy Ground, Anguilla,B.W.I. | Soufriere Bay, Saint Lucia | South Friars Bay, St. Kitts & Nevis | Terre De Haut, Îles des Saintes, Guadeloupe, F.W.I. | $4,391 Up To $500 Onboard Credit | | Onboard Credit! | View Itinerary | Get FREE Quote |
| Mar 15, 2025 | SeaDream Yacht Club | SeaDream I | Caribbean | Philipsburg | Bridgetown | 7 Nights | Bridgetown, Barbados, Barbados | Deshaies, Guadeloupe, F.W.I. | Gustavia, St. Barths, F.W.I. | Mayreau, St. Vincent and the Grenadines | Philipsburg, Sint Maarten, Dutch Caribbean | Rodney Bay, Saint Lucia | Sandy Ground, Anguilla,B.W.I. | Soufriere Bay, Saint Lucia | Terre De Haut, Îles des Saintes, Guadeloupe, F.W.I. | $4,391 Up To $500 Onboard Credit | | Onboard Credit! | View Itinerary | Get FREE Quote |
| 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. | $4,391 Up To $500 Onboard Credit | | | View Itinerary | Get FREE Quote |
| Feb 08, 2025 | SeaDream Yacht Club | SeaDream I | Caribbean | Philipsburg | Bridgetown | 7 Nights | Bridgetown, Barbados, Barbados | Gustavia, St. Barths, F.W.I. | Mayreau, St. Vincent and the Grenadines | Philipsburg, Sint Maarten, Dutch Caribbean | Rodney Bay, Saint Lucia | Sandy Ground, Anguilla,B.W.I. | Sint Eustatius, Netherlands Antilles | Soufriere Bay, Saint Lucia | Terre De Haut, Îles des Saintes, Guadeloupe, F.W.I. | $4,399 Up To $500 Onboard Credit | | Onboard Credit! | View Itinerary | Get FREE Quote |
24 reviews | Feb 22, 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 | $4,399 Up To $500 Onboard Credit | | Onboard Credit! | View Itinerary | Get FREE Quote |
24 reviews | Feb 15, 2025 | Windstar | Wind Surf | Caribbean - Eastern | 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 | $4,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
| Jan 25, 2025 | SeaDream Yacht Club | SeaDream I | Caribbean | Philipsburg | Philipsburg | 7 Nights | Charlestown, Nevis, St. Kitts & Nevis | 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. | $4,691 Up To $500 Onboard Credit | | | View Itinerary | Get FREE Quote |