Windstar Cruises Cruises to Caribbean - Southern 80 cruises on Windstar Cruises found
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80 cruises found
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Ports
- Bridgetown, Barbados
- Pigeon Island, St. Lucia
- Castries, St. Lucia
- Anse Mitan, Martinique
- Mayreau, Grenadines
- St. George's, Grenada
- Bequia, Grenadines
Ports
Bridgetown, Barbados - Pigeon Island, St. Lucia - Castries, St. Lucia - Anse Mitan, Martinique - Mayreau, Grenadines - St. George's, Grenada - Bequia, Grenadines - View more ports
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
- Miami, Florida
- Puerto Plata, Dominican Republic
- Samana, Dominican Republic
- Jost Van Dyke, B.V.I.
- Prickly Pear Island, B.V.I.
- Soper's Hole, Tortola, B.V.I.
- San Juan, Puerto Rico
Ports
Miami, Florida - Puerto Plata, Dominican Republic - Samana, Dominican Republic - Jost Van Dyke, B.V.I. - Prickly Pear Island, B.V.I. - Soper's Hole, Tortola, B.V.I. - San Juan, Puerto Rico - View more ports
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.
- Bequia, Grenadines
- Mayreau, Grenadines
- Soufriere, St. Lucia
- Terre-De-Haut, Iles Des Saintes, Guadeloupe
- Marigot, Saint Martin
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. - Bequia, Grenadines - Mayreau, Grenadines - Soufriere, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Marigot, Saint Martin - View more ports
14 Night Star Collector: Lovely Leewards (San Juan Roundtrip)
2026 sail dates: Jan 23,
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.
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. - View more ports
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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
- San Juan, Puerto Rico
- Bequia, Grenadines
- Mayreau, Grenadines
- Soufriere, St. Lucia
- Terre-De-Haut, Iles Des Saintes, Guadeloupe
- Marigot, Saint Martin
Ports
San Juan, Puerto Rico - Bequia, Grenadines - Mayreau, Grenadines - Soufriere, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Marigot, Saint Martin - View more ports
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
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
- Charlestown, Nevis
- Roseau, Dominica
- Pigeon Island, St. Lucia
- Terre-De-Haut, Iles Des Saintes, Guadeloupe
- Basseterre, St. Kitts
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 - Charlestown, Nevis - Roseau, Dominica - Pigeon Island, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Basseterre, St. Kitts - View more ports
Ports
- Philipsburg, St. Maarten
- Charlestown, Nevis
- Roseau, Dominica
- Pigeon Island, St. Lucia
- Terre-De-Haut, Iles Des Saintes, Guadeloupe
- Gustavia, St. Barthelemy
- Basseterre, St. Kitts
- Soper's Hole, Tortola, B.V.I.
- Jost Van Dyke, B.V.I.
- Spanish Town, Virgin Gorda, B.V.I.
- ROAD BAY, ANGUILLA
- Falmouth Harbour,Antigua
Ports
Philipsburg, St. Maarten - Charlestown, Nevis - Roseau, Dominica - Pigeon Island, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Gustavia, St. Barthelemy - Basseterre, St. Kitts - Soper's Hole, Tortola, B.V.I. - Jost Van Dyke, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - ROAD BAY, ANGUILLA - Falmouth Harbour,Antigua - View more ports
All prices are per person based on double occupancy and do not include port/government fees and gratuities.