| 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 | | 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 | | | View Itinerary | Get FREE Quote |
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| 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 |
| Feb 01, 2025 | SeaDream Yacht Club | SeaDream I | Caribbean | Philipsburg | Philipsburg | 7 Nights | Falmouth Bay, Antigua and Barbuda | Gustavia, St. Barths, F.W.I. | Norman Island, B. V. I. | Philipsburg, Sint Maarten, Dutch Caribbean | Prickly Pear, B.V.I, B. V. I. | South Friars Bay, St. Kitts & Nevis | Spanish Town, Virgin Gorda, B. V. I. | Terre De Haut, Îles des Saintes, Guadeloupe, F.W.I. | $4,691 Up To $500 Onboard Credit | | Onboard Credit! | View Itinerary | Get FREE Quote |
2 reviews | Jan 18, 2026 | SeaDream Yacht Club | SeaDream II | Caribbean | Philipsburg | San Juan del Sur | 7 Nights | Charlestown, Nevis, St. Kitts & Nevis | Falmouth Bay, Antigua and Barbuda | Gustavia, St. Barths, F.W.I. | Philipsburg, Sint Maarten, Dutch Caribbean | Saba, Netherlands Antilles | San Juan, Puerto Rico | Terre De Haut, Îles des Saintes, Guadeloupe, F.W.I. | White Bay, Jost van Dyke, B. V. I. | $4,791 Up To $500 Onboard Credit | | | View Itinerary | Get FREE Quote |
2 reviews | Mar 01, 2026 | SeaDream Yacht Club | SeaDream II | Caribbean | Philipsburg | Charlotte Amalie | 7 Nights | Charlestown, Nevis, St. Kitts & Nevis | Charlotte Amalie, St. Thomas, U.S.V.I. | Falmouth Bay, Antigua and Barbuda | Gustavia, St. Barths, F.W.I. | Iles des Saintes, Guadeloupe, F.W.I. | Philipsburg, Sint Maarten, Dutch Caribbean | Saba, Netherlands Antilles | White Bay, Jost van Dyke, B. V. I. | $4,791 Up To $500 Onboard Credit | | | View Itinerary | Get FREE Quote |
| 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 | | Onboard Credit! | 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 |
11 reviews | Jan 14, 2026 | Windstar | Wind Spirit | Caribbean | Philipsburg | Philipsburg | 17 Nights | Anse Mitan | Bequia | Castries | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Mayreau | Road Bay | Roseau | Soper's Hole | St. George's | St. Maarten | Virgin Gorda / Prickly Pear | $4,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
| Dec 21, 2024 | 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 | Sandy Ground, Anguilla,B.W.I. | White Bay, Jost van Dyke, B. V. I. | $5,091 Up To $750 Onboard Credit | | Onboard Credit! | View Itinerary | Get FREE Quote |
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 |
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 |
11 reviews | Feb 21, 2026 | Windstar | Wind Spirit | Caribbean | Philipsburg | Bridgetown | 21 Nights | Anse Mitan | 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 | $6,099 Up To $750 Onboard Credit | | | View Itinerary | Get FREE Quote |
24 reviews | Jan 04, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Bridgetown | 21 Nights | Anse Mitan | Basseterre | Bequia | Bridgetown | Castries | Deshaies | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | Mayreau | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. George's | St. Maarten | Virgin Gorda / Prickly Pear | $6,299 Up To $750 Onboard Credit | | | View Itinerary | Get FREE Quote |
| Dec 28, 2024 | SeaDream Yacht Club | SeaDream I | Caribbean | Philipsburg | Philipsburg | 7 Nights | Falmouth Bay, Antigua and Barbuda | Gustavia, St. Barths, F.W.I. | Norman Island, B. V. I. | Philipsburg, Sint Maarten, Dutch Caribbean | Spanish Town, Virgin Gorda, B. V. I. | Terre De Haut, Îles des Saintes, Guadeloupe, F.W.I. | White Bay, Jost van Dyke, B. V. I. | $6,791 Up To $750 Onboard Credit | | Onboard Credit! | View Itinerary | Get FREE Quote |