11 reviews | Feb 28, 2026 | Windstar | Wind Spirit | Caribbean | Philipsburg | Bridgetown | 7 Nights | Basseterre | Bridgetown | Gustavia | Les Saintes | Little Bay | Pigeon Island | Roseau | St. Maarten | $2,399 Up To $250 Onboard Credit | | |
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! |
24 reviews | Feb 28, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,299 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Feb 28, 2026 | 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) |
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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. | $4,399 Up To $500 Onboard Credit | | |
24 reviews | Mar 07, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $2,399 Up To $250 Onboard Credit | | |
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 | $6,219 Up To $750 Onboard Credit | | Suite! |
24 reviews | Mar 14, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $2,399 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Mar 14, 2026 | 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 Up To $500 Onboard Credit | | |
24 reviews | Mar 21, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,299 Up To $250 Onboard Credit | | |
24 reviews | Mar 21, 2026 | 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 Up To $500 Onboard Credit | | |
24 reviews | Mar 28, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $2,399 Up To $250 Onboard Credit | | Onboard Credit! |
| 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. | $4,399 Up To $500 Onboard Credit | | |