9 reviews | Jan 25, 2025 | Seabourn | Ovation | Caribbean | Philipsburg | Bridgetown | 21 Nights | Antigua | Aruba | Bonaire, Netherlands Antilles | Bridgetown, Barbados | Cartagena, Colombia | Curacao, Netherlands | Fort-De-France, Martinique | Isla Catalina, Dominican Republic | Philipsburg, St. Maarten | Port Elizabeth, Bequia | Santa Marta, Colombia | Santo Domingo, Dom Rep. | $10,400 Up To $1000 Onboard Credit Welcome Reception Exclusive Amenity Distinctive Host | | *Distinctive Voyage | 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 | | | 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 | | Balcony! | View Itinerary | Get FREE Quote |
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5 reviews | Jan 18, 2026 | Silversea | Silver Shadow | Caribbean | Philipsburg | Bridgetown | 7 Nights | Bridgetown | Gustavia, Saint Barthélemy | Kingstown, St. Vincent | Philipsburg, St. Maarten | Roseau, Dominica | St. John, Virgin Islands | $5,700 Up To $750 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 | Bridgetown | Gustavia, Saint Barthélemy | Kingstown, St. Vincent | 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 | 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 |
24 reviews | Jan 04, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Oranjestad | 28 Nights | Anse Mitan | Basseterre | Bequia | Bridgetown | Castries | Deshaies | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Kralendijk | Little Bay | Man-O-War Bay | Mayreau | Oranjestad | Pigeon Island | Road Bay | Roseau | Soper's Hole | Soufriere | St. George's | St. Maarten | Virgin Gorda / Prickly Pear | Willemstad | $8,399 Up To $1000 Onboard Credit | | Onboard Credit! | View Itinerary | Get FREE Quote |
24 reviews | Jan 04, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 55 Nights | Anse Mitan | Basseterre | Belize City | Bequia | Bocas del Toro | Bridgetown | Cartagena | Castries | Cayman Brac | Colón | Costa Maya | Cozumel | Deshaies | Falmouth Harbour | Grand Cayman | Gustavia | Isla San Andres | Jost Van Dyke, Great Harbour | Kralendijk | La Romana | Little Bay | Man-O-War Bay | Mayreau | Oranjestad | Pigeon Island | Port Antonio | Road Bay | Roatan | Roseau | Santa Marta | Santo Domingo | Soper's Hole | Soufriere | St. George's | St. Maarten | Virgin Gorda / Prickly Pear | Willemstad | $16,699 Up To $1000 Onboard Credit | | Onboard Credit! | 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 |
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 |
11 reviews | Jan 14, 2026 | Windstar | Wind Spirit | Caribbean | Philipsburg | Philipsburg | 10 Nights | Anse Mitan | Bequia | Castries | Gustavia | Les Saintes | Little Bay | Mayreau | Roseau | St. George's | St. Maarten | $3,499 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 | 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 | | Onboard Credit! | 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 |