5 reviews | Aug 02, 2024 | Windstar | Star Legend | Baltic | Stockholm | Copenhagen | 10 Nights | Copenhagen | Gdansk | Helsinki | Klaipeda | Riga | Sassnitz, Germany | Stockholm | Tallinn | Visby | Warnemünde (Berlin) | $5,899 Up To $750 Onboard Credit | | |
15 reviews | Oct 19, 2025 | Windstar | Star Pride | Bermuda | New York (Manhattan) | San Juan | 7 Nights | San Juan | St. George's | $2,699 Up To $300 Onboard Credit | | Suite! |
15 reviews | Oct 12, 2024 | Windstar | Star Pride | Canada | Montreal | San Juan | 22 Nights | Bar Harbor | Basseterre | Boston | Cap aux Meules | Gaspe | Gustavia | Halifax | Hamilton | Louisbourg | Lunenburg | Montreal | Portland | Quebec City | San Juan | St. George's | Virgin Gorda | $6,929 Up To $750 Onboard Credit | | Suite! |
15 reviews | Oct 07, 2025 | Windstar | Star Pride | Canada | Montreal | New York (Manhattan) | 12 Nights | Cap aux Meules | Gaspe | Halifax | Louisbourg | Montreal | Portland | Quebec City | $5,239 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
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15 reviews | Oct 23, 2024 | Windstar | Star Pride | Caribbean | Boston | San Juan | 11 Nights | Basseterre | Boston | Gustavia | Hamilton | San Juan | St. George's | Virgin Gorda | $2,899 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Nov 09, 2024 | Windstar | Star Pride | Caribbean | San Juan | San Juan | 14 Nights | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | St. Thomas | Virgin Gorda / Prickly Pear | $4,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Nov 27, 2024 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 10 Nights | Bridgetown | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | Soper's Hole | Virgin Gorda / Prickly Pear | $3,699 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Dec 07, 2024 | Windstar | Star Pride | Caribbean | San Juan | Oranjestad | 14 Nights | Bridgetown | Gustavia | Kralendijk | Little Bay | Man-O-War Bay | Mayreau | Oranjestad | Pigeon Island | Roseau | San Juan | Soufriere | St. George's | St. Thomas | Willemstad | $4,199 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Dec 07, 2024 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 14 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Kingstown | Les Saintes | Little Bay | Mayreau | Pigeon Island | Roseau | St. George's | The Pitons | $4,099 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Dec 14, 2024 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 14 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Kingstown | Les Saintes | Little Bay | Mayreau | Pigeon Island | Roseau | St. George's | The Pitons | $4,999 Up To $750 Onboard Credit | | Onboard Credit! |
11 reviews | Dec 14, 2024 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bridgetown | Les Saintes | Little Bay | Pigeon Island | Roseau | $2,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Dec 21, 2024 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 14 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Kingstown | Les Saintes | Little Bay | Mayreau | Pigeon Island | Roseau | St. George's | The Pitons | $4,699 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Dec 28, 2024 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 14 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Kingstown | Les Saintes | Little Bay | Mayreau | Pigeon Island | Roseau | St. George's | The Pitons | $4,399 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Dec 28, 2024 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bridgetown | Les Saintes | Little Bay | Pigeon Island | Roseau | $2,899 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Jan 04, 2025 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 14 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Kingstown | Les Saintes | Little Bay | Mayreau | Pigeon Island | Roseau | St. George's | The Pitons | $4,199 Up To $500 Onboard Credit | | |
11 reviews | Jan 11, 2025 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 14 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Kingstown | Les Saintes | Little Bay | Mayreau | Pigeon Island | Roseau | St. George's | The Pitons | $4,399 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Jan 11, 2025 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bridgetown | Les Saintes | Little Bay | Pigeon Island | Roseau | $2,699 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Jan 18, 2025 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 14 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Kingstown | Les Saintes | Little Bay | Mayreau | Pigeon Island | Roseau | St. George's | The Pitons | $4,299 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
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 | $4,599 Up To $500 Onboard Credit | | |
11 reviews | Jan 25, 2025 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 14 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Kingstown | Les Saintes | Little Bay | Mayreau | Pigeon Island | Roseau | St. George's | The Pitons | $4,299 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |