Windstar Cruises Cruises to Caribbean - Southern 80 cruises on Windstar Cruises found
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80 cruises found
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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
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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
- 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
- Bridgetown, Barbados
- Little Bay, Montserrat
- Terre-De-Haut, Iles Des Saintes, Guadeloupe
- Roseau, Dominica
- Anse Mitan, Martinique
- Pigeon Island, St. Lucia
- Castries, St. Lucia
- Kingstown, St. Vincent
- Mayreau, Grenadines
- St. George's, Grenada
- Bequia, Grenadines
Ports
Bridgetown, Barbados - Little Bay, Montserrat - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Roseau, Dominica - Anse Mitan, Martinique - Pigeon Island, St. Lucia - Castries, St. Lucia - Kingstown, St. Vincent - Mayreau, Grenadines - St. George's, Grenada - Bequia, Grenadines - View more ports
Ports
- San Juan, Puerto Rico
- Marigot, Saint Martin
- Terre-De-Haut, Iles Des Saintes, Guadeloupe
- Mayreau, Grenadines
- Bequia, Grenadines
- Pigeon Island, St. Lucia
- CRUISE THE PITONS, ST. LUCIA
Ports
San Juan, Puerto Rico - Marigot, Saint Martin - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Mayreau, Grenadines - Bequia, Grenadines - Pigeon Island, St. Lucia - CRUISE THE PITONS, ST. LUCIA - View more ports
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Top critical review
| Partners | Bonus Offers | Inside | Oceanview | Balcony | Suite | |
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$3033* |
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$3033* |
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$3033* |
Ports
- Philipsburg, St. Maarten
- Roseau, Dominica
- Pigeon Island, St. Lucia
- Terre-De-Haut, Iles Des Saintes, Guadeloupe
- Gustavia, St. Barthelemy
- Basseterre, St. Kitts
- Falmouth Harbour,Antigua
- ROAD BAY, ANGUILLA
- Jost Van Dyke, B.V.I.
- Soper's Hole, Tortola, B.V.I.
Ports
Philipsburg, St. Maarten - Roseau, Dominica - Pigeon Island, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Gustavia, St. Barthelemy - Basseterre, St. Kitts - Falmouth Harbour,Antigua - ROAD BAY, ANGUILLA - Jost Van Dyke, B.V.I. - Soper's Hole, Tortola, B.V.I. - View more ports
Ports
- Bridgetown, Barbados
- Pigeon Island, St. Lucia
- Castries, St. Lucia
- CRUISE THE PITONS, ST. LUCIA
- Kingstown, St. Vincent
- Mayreau, Grenadines
- St. George's, Grenada
- Bequia, Grenadines
Ports
Bridgetown, Barbados - Pigeon Island, St. Lucia - Castries, St. Lucia - CRUISE THE PITONS, ST. LUCIA - Kingstown, St. Vincent - Mayreau, Grenadines - St. George's, Grenada - Bequia, Grenadines - 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
- San Juan, Puerto Rico
- Cruz Bay, St. John, U.S.V.I.
- St. John's, Antigua
- Terre-De-Haut, Iles Des Saintes, Guadeloupe
- Pigeon Island, St. Lucia
- St. George's, Grenada
- Gustavia, St. Barthelemy
- Jost Van Dyke, B.V.I.
- Prickly Pear Island, B.V.I.
- Catalina Island (Isla Catalina), Dominican Republic
- Santo Domingo, Dominican Republic
- Cartagena, Colombia
- San Blas Islands, Panama
- Colon, Panama
Ports
San Juan, Puerto Rico - Cruz Bay, St. John, U.S.V.I. - St. John's, Antigua - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Pigeon Island, St. Lucia - St. George's, Grenada - Gustavia, St. Barthelemy - Jost Van Dyke, B.V.I. - Prickly Pear Island, B.V.I. - Catalina Island (Isla Catalina), Dominican Republic - Santo Domingo, Dominican Republic - Cartagena, Colombia - San Blas Islands, Panama - Colon, Panama - View more ports
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Top critical review
| Partners | Bonus Offers | Inside | Oceanview | Balcony | Suite | |
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N/A |
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$5684* |
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$6143* |
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$6143* |
Ports
- San Juan, Puerto Rico
- Cruz Bay, St. John, U.S.V.I.
- St. John's, Antigua
- Terre-De-Haut, Iles Des Saintes, Guadeloupe
- Pigeon Island, St. Lucia
- St. George's, Grenada
- Gustavia, St. Barthelemy
- Jost Van Dyke, B.V.I.
- Prickly Pear Island, B.V.I.
Ports
San Juan, Puerto Rico - Cruz Bay, St. John, U.S.V.I. - St. John's, Antigua - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Pigeon Island, St. Lucia - St. George's, Grenada - Gustavia, St. Barthelemy - Jost Van Dyke, B.V.I. - Prickly Pear Island, B.V.I. - View more ports
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Top critical review
| Partners | Bonus Offers | Inside | Oceanview | Balcony | Suite | |
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$4057* |
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$4543* |
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$4543* |
Ports
- San Juan, Puerto Rico
- Catalina Island (Isla Catalina), Dominican Republic
- Santo Domingo, Dominican Republic
- Cartagena, Colombia
- San Blas Islands, Panama
- Colon, Panama
Ports
San Juan, Puerto Rico - Catalina Island (Isla Catalina), Dominican Republic - Santo Domingo, Dominican Republic - Cartagena, Colombia - San Blas Islands, Panama - Colon, Panama - View more ports
Top positive review
Top critical review
| Partners | Bonus Offers | Inside | Oceanview | Balcony | Suite | |
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$3226* |
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$3605* |
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$3605* |
All prices are per person based on double occupancy and do not include port/government fees and gratuities.