| Nov 14, 2026 | SeaDream Yacht Club | SeaDream I | Caribbean | Philipsburg | Bridgetown | 7 Nights | Bridgetown, Barbados, Barbados | Gustavia, St. Barths, F.W.I. | Leverick Bay, Virgin Gorda, B. V. I. | Mayreau, St. Vincent and the Grenadines | Norman Island, B. V. I. | Philipsburg, Sint Maarten, Dutch Caribbean | Soper's Hole, Tortola, B. V. I. | Spanish Town, Virgin Gorda, B. V. I. | Terre De Haut, Îles des Saintes, Guadeloupe, F.W.I. | $4,791 Up To $500 Onboard Credit | | | View Itinerary | Get FREE Quote |
5 reviews | Jan 04, 2026 | Silversea | Silver Shadow | Caribbean | Philipsburg | Philipsburg | 7 Nights | Les Saintes, Guadeloupe | Little Bay, Montserrat, Montserrat | Philipsburg, St. Maarten | St. Johns, Antigua | St. Thomas, Virgin Islands | $5,700 Up To $750 Onboard Credit | | | View Itinerary | Get FREE Quote |
5 reviews | Jan 11, 2026 | Silversea | Silver Shadow | Caribbean | Philipsburg | Philipsburg | 7 Nights | Les Saintes, Guadeloupe | Little Bay, Montserrat, Montserrat | Philipsburg, St. Maarten | St. Johns, Antigua | St. Thomas, Virgin Islands | $5,700 Up To $750 Onboard Credit | | | View Itinerary | Get FREE Quote |
5 reviews | Jan 18, 2026 | Silversea | Silver Shadow | Caribbean | Philipsburg | Bridgetown | 7 Nights | Gustavia, Saint Barthélemy | Philipsburg, St. Maarten | Roseau, Dominica | St. John, Virgin Islands | $5,700 Up To $750 Onboard Credit | | | View Itinerary | Get FREE Quote |
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5 reviews | Feb 19, 2026 | Silversea | Silver Shadow | Caribbean | Philipsburg | Philipsburg | 7 Nights | Les Saintes, Guadeloupe | Little Bay, Montserrat, Montserrat | Philipsburg, St. Maarten | St. Johns, Antigua | St. Thomas, Virgin Islands | $5,500 Up To $750 Onboard Credit | | Balcony! | View Itinerary | Get FREE Quote |
5 reviews | Feb 26, 2026 | Silversea | Silver Shadow | Caribbean | Philipsburg | Bridgetown | 7 Nights | Gustavia, Saint Barthélemy | Philipsburg, St. Maarten | Roseau, Dominica | St. John, Virgin Islands | $5,500 Shipboard Credit Per Person ($300) | | Shipboard Credit Per Person ($300) | View Itinerary | Get FREE Quote |
24 reviews | Dec 21, 2024 | 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 | $5,699 Up To $750 Onboard Credit | | | View Itinerary | Get FREE Quote |
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 | | | View Itinerary | Get FREE Quote |
24 reviews | Dec 28, 2024 | 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 | $5,699 Up To $750 Onboard Credit | | Onboard Credit! | View Itinerary | Get FREE Quote |
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 | $3,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
24 reviews | Jan 04, 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 | $4,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
24 reviews | Jan 04, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,999 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
24 reviews | Jan 11, 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 | $4,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
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 | $2,999 Up To $300 Onboard Credit | | | View Itinerary | Get FREE Quote |
24 reviews | Jan 18, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,999 Up To $300 Onboard Credit Welcome Reception Exclusive Amenity Distinctive Host | | *Distinctive Voyage | View Itinerary | Get FREE Quote |
24 reviews | Jan 18, 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 | $4,799 Up To $500 Onboard Credit | | | View Itinerary | Get FREE Quote |
24 reviews | Jan 25, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,999 Up To $300 Onboard Credit | | | View Itinerary | Get FREE Quote |
24 reviews | Feb 01, 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 | $4,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
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 | $2,799 Up To $300 Onboard Credit | | Onboard Credit! | View Itinerary | Get FREE Quote |
24 reviews | Feb 08, 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 | $4,899 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |