Cruises on Windstar Cruises 69 cruises on Windstar Cruises found
Your search Clear selections
69 cruises found
Sort by
Filter by
Ports
- Cozumel, Mexico
- George Town, Grand Cayman
- Cayman Brac
- Port Antonio, Jamaica
- Santo Domingo, Dominican Republic
- La Romana, Dominican Republic
- Jost Van Dyke, B.V.I.
- Spanish Town, Virgin Gorda, B.V.I.
- Philipsburg, St. Maarten
- Charlestown, Nevis
- Roseau, Dominica
- Pigeon Island, St. Lucia
- Terre-De-Haut, Iles Des Saintes, Guadeloupe
- Gustavia, St. Barthelemy
- Basseterre, St. Kitts
Ports
Cozumel, Mexico - George Town, Grand Cayman - Cayman Brac - Port Antonio, Jamaica - Santo Domingo, Dominican Republic - La Romana, Dominican Republic - Jost Van Dyke, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - Philipsburg, St. Maarten - Charlestown, Nevis - Roseau, Dominica - Pigeon Island, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Gustavia, St. Barthelemy - 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
- Basseterre, St. Kitts
- Gustavia, St. Barthelemy
- Falmouth Harbour,Antigua
- ROAD BAY, ANGUILLA
- Jost Van Dyke, B.V.I.
- Soper's Hole, Tortola, B.V.I.
- Spanish Town, Virgin Gorda, B.V.I.
Ports
Philipsburg, St. Maarten - Charlestown, Nevis - Roseau, Dominica - Pigeon Island, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Basseterre, St. Kitts - Gustavia, St. Barthelemy - Falmouth Harbour,Antigua - ROAD BAY, ANGUILLA - Jost Van Dyke, B.V.I. - Soper's Hole, Tortola, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - View more ports
Ports
- Philipsburg, St. Maarten
- Falmouth Harbour,Antigua
- ROAD BAY, ANGUILLA
- Jost Van Dyke, B.V.I.
- Soper's Hole, Tortola, B.V.I.
- Spanish Town, Virgin Gorda, B.V.I.
- Gustavia, St. Barthelemy
- Basseterre, St. Kitts
- Little Bay, Montserrat
- Deshaies, Guadeloupe
- Roseau, Dominica
- Pigeon Island, St. Lucia
- Bridgetown, Barbados
- Anse Mitan, Martinique
- Castries, St. Lucia
- Bequia, Grenadines
- Mayreau, Grenadines
- St. George's, Grenada
- Charlotteville, Tobago
- Soufriere, St. Lucia
- Kralendijk, Bonaire
- Willemstad, Curacao
- Oranjestad, Aruba
- Santa Marta, Colombia
- Cartagena, Colombia
- Bocas Del Toro, Panama
- Colon, Panama
- San Andres Island (Isla San Andres), Colombia
- Coxen Hole, Roatan, Bay Islands, Honduras
- Belize City, Belize
- Costa Maya (Mahahual), Mexico
- Cozumel, Mexico
- George Town, Grand Cayman
- Cayman Brac
- Port Antonio, Jamaica
- Santo Domingo, Dominican Republic
- La Romana, Dominican Republic
Ports
Philipsburg, St. Maarten - Falmouth Harbour,Antigua - ROAD BAY, ANGUILLA - Jost Van Dyke, B.V.I. - Soper's Hole, Tortola, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - Gustavia, St. Barthelemy - Basseterre, St. Kitts - Little Bay, Montserrat - Deshaies, Guadeloupe - Roseau, Dominica - Pigeon Island, St. Lucia - Bridgetown, Barbados - Anse Mitan, Martinique - Castries, St. Lucia - Bequia, Grenadines - Mayreau, Grenadines - St. George's, Grenada - Charlotteville, Tobago - Soufriere, St. Lucia - Kralendijk, Bonaire - Willemstad, Curacao - Oranjestad, Aruba - Santa Marta, Colombia - Cartagena, Colombia - Bocas Del Toro, Panama - Colon, Panama - San Andres Island (Isla San Andres), Colombia - Coxen Hole, Roatan, Bay Islands, Honduras - Belize City, Belize - Costa Maya (Mahahual), Mexico - Cozumel, Mexico - George Town, Grand Cayman - Cayman Brac - Port Antonio, Jamaica - Santo Domingo, Dominican Republic - La Romana, Dominican Republic - View more ports
Ports
- Bridgetown, Barbados
- Charlotteville, Tobago
- Mayreau, Grenadines
- Soufriere, St. Lucia
- Kralendijk, Bonaire
- Willemstad, Curacao
- Oranjestad, Aruba
- Santa Marta, Colombia
- Cartagena, Colombia
- Bocas Del Toro, Panama
- Colon, Panama
Ports
Bridgetown, Barbados - Charlotteville, Tobago - Mayreau, Grenadines - Soufriere, St. Lucia - Kralendijk, Bonaire - Willemstad, Curacao - Oranjestad, Aruba - Santa Marta, Colombia - Cartagena, Colombia - Bocas Del Toro, Panama - Colon, Panama - View more ports
Ports
- Bridgetown, Barbados
- Charlotteville, Tobago
- Mayreau, Grenadines
- Soufriere, St. Lucia
- Kralendijk, Bonaire
- Willemstad, Curacao
- Oranjestad, Aruba
Ports
Bridgetown, Barbados - Charlotteville, Tobago - Mayreau, Grenadines - Soufriere, St. Lucia - Kralendijk, Bonaire - Willemstad, Curacao - Oranjestad, Aruba - View more ports
Ports
- Bridgetown, Barbados
- Anse Mitan, Martinique
- Pigeon Island, St. Lucia
- Castries, St. Lucia
- Bequia, Grenadines
- Mayreau, Grenadines
- St. George's, Grenada
Ports
Bridgetown, Barbados - Anse Mitan, Martinique - Pigeon Island, St. Lucia - Castries, St. Lucia - Bequia, Grenadines - Mayreau, Grenadines - St. George's, Grenada - View more ports
Ports
- Philipsburg, St. Maarten
- Basseterre, St. Kitts
- Little Bay, Montserrat
- Gustavia, St. Barthelemy
- Deshaies, Guadeloupe
- Roseau, Dominica
- Pigeon Island, St. Lucia
- Bridgetown, Barbados
- Anse Mitan, Martinique
- Castries, St. Lucia
- Bequia, Grenadines
- Mayreau, Grenadines
- St. George's, Grenada
Ports
Philipsburg, St. Maarten - Basseterre, St. Kitts - Little Bay, Montserrat - Gustavia, St. Barthelemy - Deshaies, Guadeloupe - Roseau, Dominica - Pigeon Island, St. Lucia - Bridgetown, Barbados - Anse Mitan, Martinique - Castries, St. Lucia - Bequia, Grenadines - Mayreau, Grenadines - St. George's, Grenada - View more ports
Ports
- Bridgetown, Barbados
- Roseau, Dominica
- Castries, St. Lucia
- Anse Mitan, Martinique
- Pigeon Island, St. Lucia
Ports
Bridgetown, Barbados - Roseau, Dominica - Castries, St. Lucia - Anse Mitan, Martinique - Pigeon Island, St. Lucia - View more ports
| Partners | Bonus Offers | Inside | Oceanview | Balcony | Suite | |
|---|---|---|---|---|---|---|
|
|
N/A |
$4229* |
N/A |
N/A |
||
|
|
See Offers |
N/A |
$4229* |
N/A |
N/A |
|
|
|
N/A |
$4229* |
N/A |
N/A |
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
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 - View more ports
7 Night Classic Caribbean (Philipsburg Roundtrip)
2025 sail dates: Jan 04, Dec 07, Dec 21
2026 sail dates: Feb 28,
| Partners | Bonus Offers | Inside | Oceanview | Balcony | Suite | |
|---|---|---|---|---|---|---|
|
|
N/A |
$3551* |
N/A |
$4151* |
||
|
|
See Offers |
N/A |
$3551* |
N/A |
$6251* |
|
|
|
N/A |
$3551* |
N/A |
$6251* |
||
|
|
N/A |
$2351* |
N/A |
$3251* |
||
|
|
See Offers |
N/A |
$2419* |
N/A |
$5319* |
|
|
|
N/A |
$2419* |
N/A |
$5319* |
||
|
|
N/A |
$2751* |
N/A |
$3651* |
||
|
|
See Offers |
N/A |
$2819* |
N/A |
$5719* |
|
|
|
N/A |
$2819* |
N/A |
$5719* |
||
|
|
N/A |
$2551* |
N/A |
$3451* |
||
|
|
See Offers |
N/A |
$2619* |
N/A |
$5519* |
|
|
|
N/A |
$2619* |
N/A |
$5519* |
||
|
|
N/A |
$2351* |
N/A |
$3251* |
||
|
|
See Offers |
N/A |
$2419* |
N/A |
$5319* |
|
|
|
N/A |
$2419* |
N/A |
$5319* |
Ports
- Oranjestad, Aruba
- Willemstad, Curacao
- Kralendijk, Bonaire
- Soufriere, St. Lucia
- Mayreau, Grenadines
- Charlotteville, Tobago
- Bridgetown, Barbados
Ports
Oranjestad, Aruba - Willemstad, Curacao - Kralendijk, Bonaire - Soufriere, St. Lucia - Mayreau, Grenadines - Charlotteville, Tobago - Bridgetown, Barbados - View more ports
7 Night Windward Ways & Tobago Cays (Oranjestad To Bridgetown)
Star Pride XL
2025 sail dates: Mar 15,
All prices are per person based on double occupancy and do not include port/government fees and gratuities.