9 reviews | Jan 11, 2025 | Seabourn | Ovation | Caribbean | Philipsburg | Philipsburg | 14 Nights | Antigua | Bridgetown, Barbados | Fort-De-France, Martinique | Grenada | Jost Van Dyke, B.V.I. | Philipsburg, St. Maarten | Port Elizabeth, Bequia | St. Lucia | $8,259 Up To $1000 Onboard Credit Welcome Reception Exclusive Amenity Distinctive Host | | *Distinctive Voyage |
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 | Grenada | Isla Catalina, Dominican Republic | Philipsburg, St. Maarten | Port Elizabeth, Bequia | Santa Marta, Colombia | Santo Domingo, Dom Rep. | $12,670 Up To $1000 Onboard Credit Welcome Reception Exclusive Amenity Distinctive Host | | *Distinctive Voyage |
9 reviews | Feb 22, 2025 | Seabourn | Ovation | Caribbean | Philipsburg | Philipsburg | 14 Nights | Antigua | Bridgetown, Barbados | Fort-De-France, Martinique | Grenada | Jost Van Dyke, B.V.I. | Philipsburg, St. Maarten | Port Elizabeth, Bequia | St. Lucia | $8,547 Up To $1000 Onboard Credit Welcome Reception Exclusive Amenity Distinctive Host | | *Distinctive Voyage |
9 reviews | Mar 08, 2025 | Seabourn | Ovation | Caribbean | Philipsburg | Lisbon | 19 Nights | Bridgetown, Barbados | Fort-De-France, Martinique | Grenada | Lisbon, Portugal | Madeira, Portugal | Philipsburg, St. Maarten | Port Elizabeth, Bequia | Saint Pierre et Miquelon, France | $10,193 Up To $1000 Onboard Credit Welcome Reception Exclusive Amenity Distinctive Host | | *Distinctive Voyage |
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9 reviews | Jan 17, 2026 | Seabourn | Ovation | Caribbean | Philipsburg | Philipsburg | 14 Nights | Antigua | Bridgetown, Barbados | Grenada | Jost Van Dyke, B.V.I. | Philipsburg, St. Maarten | Port Elizabeth, Bequia | Saint Pierre et Miquelon, France | St. Lucia | $7,241 Up To $750 Onboard Credit | | |
9 reviews | Jan 31, 2026 | Seabourn | Ovation | Caribbean | Philipsburg | Bridgetown | 14 Nights | Bridgetown, Barbados | Grenada | Philipsburg, St. Maarten | Port Elizabeth, Bequia | Rodney Bay, Saint Lucia | Roseau, Dominica | Saint Pierre et Miquelon, France | $7,357 Up To $750 Onboard Credit | | Suite! |
9 reviews | Feb 21, 2026 | Seabourn | Ovation | Caribbean | Philipsburg | Philipsburg | 14 Nights | Antigua | Bridgetown, Barbados | Grenada | Jost Van Dyke, B.V.I. | Philipsburg, St. Maarten | Port Elizabeth, Bequia | Saint Pierre et Miquelon, France | St. Lucia | $7,241 Up To $750 Onboard Credit | | Suite! |
9 reviews | Mar 07, 2026 | Seabourn | Ovation | Caribbean | Philipsburg | Bridgetown | 14 Nights | Bridgetown, Barbados | Grenada | Philipsburg, St. Maarten | Port Elizabeth, Bequia | Rodney Bay, Saint Lucia | Roseau, Dominica | Saint Pierre et Miquelon, France | $7,357 Up To $750 Onboard Credit | | |
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 | $4,499 Up To $500 Onboard Credit | | Onboard Credit! |
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 | $3,999 Up To $500 Onboard Credit | | |
24 reviews | 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 | 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) |
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) |
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 | $3,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
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 | $5,999 Up To $750 Onboard Credit | | Onboard Credit! |
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 | $7,899 Up To $1000 Onboard Credit | | Onboard Credit! |
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 | $15,599 Up To $1000 Onboard Credit | | |
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 | $3,999 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
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) |
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) |