Windstar Cruises Cruises to Caribbean - Southern 81 cruises on Windstar Cruises found
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81 cruises found
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Ports
- Bridgetown, Barbados
- Little Bay, Montserrat
- Terre-De-Haut, Iles Des Saintes, Guadeloupe
- Roseau, Dominica
- Anse Mitan, Martinique
- Pigeon Island, St. Lucia
Ports
Bridgetown, Barbados - Little Bay, Montserrat - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Roseau, Dominica - Anse Mitan, Martinique - Pigeon Island, St. Lucia - View more ports
7 Night Jewels Of The Windward Islands (Bridgetown Roundtrip)
2026 sail dates: Mar 07,
Ports
- San Juan, Puerto Rico
- Cruz Bay, St. John, U.S.V.I.
- Basseterre, St. Kitts
- Gustavia, St. Barthelemy
- Philipsburg, St. Maarten
- Jost Van Dyke, B.V.I.
- Prickly Pear Island, B.V.I.
- Marigot, Saint Martin
- Terre-De-Haut, Iles Des Saintes, Guadeloupe
- Mayreau, Grenadines
- Bequia, Grenadines
- CRUISE THE PITONS, ST. LUCIA
- Pigeon Island, St. Lucia
Ports
San Juan, Puerto Rico - Cruz Bay, St. John, U.S.V.I. - Basseterre, St. Kitts - Gustavia, St. Barthelemy - Philipsburg, St. Maarten - Jost Van Dyke, B.V.I. - Prickly Pear Island, B.V.I. - Marigot, Saint Martin - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Mayreau, Grenadines - Bequia, Grenadines - CRUISE THE PITONS, ST. LUCIA - Pigeon Island, St. Lucia - View more ports
Top positive review
Top critical review
| Partners | Bonus Offers | Inside | Oceanview | Balcony | Suite | |
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$6096* |
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$7296* |
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$7296* |
Ports
- Philipsburg, St. Maarten
- Soper's Hole, Tortola, B.V.I.
- Jost Van Dyke, B.V.I.
- Spanish Town, Virgin Gorda, B.V.I.
- Gustavia, St. Barthelemy
- ROAD BAY, ANGUILLA
- Falmouth Harbour,Antigua
Ports
Philipsburg, St. Maarten - Soper's Hole, Tortola, B.V.I. - Jost Van Dyke, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - Gustavia, St. Barthelemy - ROAD BAY, ANGUILLA - Falmouth Harbour,Antigua - View more ports
Ports
- Oranjestad, Aruba
- Kralendijk, Bonaire
- CRUISE THE PITONS, ST. LUCIA
- Pigeon Island, St. Lucia
- Bequia, Grenadines
- Mayreau, Grenadines
- Charlotteville, Tobago
- Bridgetown, Barbados
Ports
Oranjestad, Aruba - Kralendijk, Bonaire - CRUISE THE PITONS, ST. LUCIA - Pigeon Island, St. Lucia - Bequia, Grenadines - Mayreau, Grenadines - Charlotteville, Tobago - Bridgetown, Barbados - View more ports
| Partners | Bonus Offers | Inside | Oceanview | Balcony | Suite | |
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$2619* |
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$2619* |
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$2619* |
Ports
- Philipsburg, St. Maarten
- Little Bay, Montserrat
- Roseau, Dominica
- Castries, St. Lucia
- Mayreau, Grenadines
- St. George's, Grenada
- Bequia, Grenadines
- Anse Mitan, Martinique
- Terre-De-Haut, Iles Des Saintes, Guadeloupe
- Gustavia, St. Barthelemy
- Jost Van Dyke, B.V.I.
- Soper's Hole, Tortola, B.V.I.
- Spanish Town, Virgin Gorda, B.V.I.
- ROAD BAY, ANGUILLA
- Falmouth Harbour,Antigua
Ports
Philipsburg, St. Maarten - Little Bay, Montserrat - Roseau, Dominica - Castries, St. Lucia - Mayreau, Grenadines - St. George's, Grenada - Bequia, Grenadines - Anse Mitan, Martinique - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Gustavia, St. Barthelemy - Jost Van Dyke, B.V.I. - Soper's Hole, Tortola, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - ROAD BAY, ANGUILLA - Falmouth Harbour,Antigua - View more ports
| Partners | Bonus Offers | Inside | Oceanview | Balcony | Suite | |
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$4994* |
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Ports
- San Juan, Puerto Rico
- Basseterre, St. Kitts
- Gustavia, St. Barthelemy
- Philipsburg, St. Maarten
- Jost Van Dyke, B.V.I.
- Spanish Town, Virgin Gorda, B.V.I.
Ports
San Juan, Puerto Rico - Basseterre, St. Kitts - Gustavia, St. Barthelemy - Philipsburg, St. Maarten - Jost Van Dyke, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - View more ports
| Partners | Bonus Offers | Inside | Oceanview | Balcony | Suite | |
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$2662* |
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$2662* |
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$2662* |
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$2862* |
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$2893* |
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$2893* |
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$2662* |
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$2693* |
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$2693* |
Ports
- San Juan, Puerto Rico
- St. George's, Grenada
- Bequia, Grenadines
- Pigeon Island, St. Lucia
- Terre-De-Haut, Iles Des Saintes, Guadeloupe
- Philipsburg, St. Maarten
Ports
San Juan, Puerto Rico - St. George's, Grenada - Bequia, Grenadines - Pigeon Island, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Philipsburg, St. Maarten - View more ports
7 Night Windward Islands Surf & Sunsets (San Juan Roundtrip)
Star Pride XL
2024 sail dates:
2025 sail dates:
| Partners | Bonus Offers | Inside | Oceanview | Balcony | Suite |
|---|
Ports
- Bridgetown, Barbados
- Bequia, Grenadines
- Mayreau, Grenadines
- St. George's, Grenada
- Kralendijk, Bonaire
- Willemstad, Curacao
- Oranjestad, Aruba
- Cartagena, Colombia
- Colon, Panama
Ports
Bridgetown, Barbados - Bequia, Grenadines - Mayreau, Grenadines - St. George's, Grenada - Kralendijk, Bonaire - Willemstad, Curacao - Oranjestad, Aruba - Cartagena, Colombia - Colon, Panama - View more ports
Ports
New York, New York - St. George's, Bermuda - San Juan, Puerto Rico - View more ports
| Partners | Bonus Offers | Inside | Oceanview | Balcony | Suite | |
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$2426* |
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$2426* |
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$2426* |
Ports
- San Juan, Puerto Rico
- Bequia, Grenadines
- Mayreau, Grenadines
- Soufriere, St. Lucia
- Terre-De-Haut, Iles Des Saintes, Guadeloupe
- Marigot, Saint Martin
- Cruz Bay, St. John, U.S.V.I.
- Basseterre, St. Kitts
- Gustavia, St. Barthelemy
- Philipsburg, St. Maarten
- Jost Van Dyke, B.V.I.
- Prickly Pear Island, B.V.I.
Ports
San Juan, Puerto Rico - Bequia, Grenadines - Mayreau, Grenadines - Soufriere, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Marigot, Saint Martin - Cruz Bay, St. John, U.S.V.I. - Basseterre, St. Kitts - Gustavia, St. Barthelemy - Philipsburg, St. Maarten - Jost Van Dyke, B.V.I. - Prickly Pear Island, B.V.I. - View more ports
Top positive review
Top critical review
| Partners | Bonus Offers | Inside | Oceanview | Balcony | Suite | |
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$5390* |
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$5390* |
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$5390* |
All prices are per person based on double occupancy and do not include port/government fees and gratuities.