Windstar Cruises Cruises to Caribbean - Southern 80 cruises on Windstar Cruises found
Your search Clear selections
80 cruises found
Sort by
Filter by
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 |
$2771* |
N/A |
$6251* |
||
|
|
See Offers |
N/A |
$2771* |
N/A |
$6251* |
|
|
|
N/A |
$2771* |
N/A |
$6251* |
||
|
|
N/A |
$2351* |
N/A |
$5251* |
||
|
|
See Offers |
N/A |
$2419* |
N/A |
$5319* |
|
|
|
N/A |
$2419* |
N/A |
$5319* |
||
|
|
N/A |
$2751* |
N/A |
$5651* |
||
|
|
See Offers |
N/A |
$2819* |
N/A |
$5719* |
|
|
|
N/A |
$2819* |
N/A |
$5719* |
||
|
|
N/A |
$2551* |
N/A |
$5451* |
||
|
|
See Offers |
N/A |
$2619* |
N/A |
$5519* |
|
|
|
N/A |
$2619* |
N/A |
$5519* |
||
|
|
N/A |
$2351* |
N/A |
$5251* |
||
|
|
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,
| Partners | Bonus Offers | Inside | Oceanview | Balcony | Suite | |
|---|---|---|---|---|---|---|
|
|
N/A |
N/A |
N/A |
$2696* |
||
|
|
See Offers |
N/A |
N/A |
N/A |
$2696* |
|
|
|
N/A |
N/A |
N/A |
$2696* |
||
|
|
N/A |
N/A |
N/A |
$3220* |
||
|
|
See Offers |
N/A |
N/A |
N/A |
$3220* |
|
|
|
N/A |
N/A |
N/A |
$3220* |
Ports
- Bridgetown, Barbados
- Charlotteville, Tobago
- Mayreau, Grenadines
- Soufriere, St. Lucia
- Willemstad, Curacao
- Kralendijk, Bonaire
- Oranjestad, Aruba
Ports
Bridgetown, Barbados - Charlotteville, Tobago - Mayreau, Grenadines - Soufriere, St. Lucia - Willemstad, Curacao - Kralendijk, Bonaire - Oranjestad, Aruba - View more ports
7 Night Windward Ways & Tobago Cays (Bridgetown To Oranjestad)
Star Pride XL
2025 sail dates: Feb 22
| Partners | Bonus Offers | Inside | Oceanview | Balcony | Suite | |
|---|---|---|---|---|---|---|
|
|
N/A |
N/A |
N/A |
$3620* |
||
|
|
See Offers |
N/A |
N/A |
N/A |
$5020* |
|
|
|
N/A |
N/A |
N/A |
$5020* |
||
|
|
N/A |
N/A |
N/A |
$3669* |
||
|
|
See Offers |
N/A |
N/A |
N/A |
$3669* |
|
|
|
N/A |
N/A |
N/A |
$3669* |
Ports
New York, New York - St. George's, Bermuda - San Juan, Puerto Rico - View more ports
| Partners | Bonus Offers | Inside | Oceanview | Balcony | Suite | |
|---|---|---|---|---|---|---|
|
|
N/A |
N/A |
N/A |
$2426* |
||
|
|
See Offers |
N/A |
N/A |
N/A |
$2426* |
|
|
|
N/A |
N/A |
N/A |
$2426* |
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 | |
|---|---|---|---|---|---|---|
|
|
N/A |
N/A |
N/A |
$2662* |
||
|
|
See Offers |
N/A |
N/A |
N/A |
$2662* |
|
|
|
N/A |
N/A |
N/A |
$2662* |
||
|
|
N/A |
N/A |
N/A |
$2862* |
||
|
|
See Offers |
N/A |
N/A |
N/A |
$2893* |
|
|
|
N/A |
N/A |
N/A |
$2893* |
||
|
|
N/A |
N/A |
N/A |
$2662* |
||
|
|
See Offers |
N/A |
N/A |
N/A |
$2693* |
|
|
|
N/A |
N/A |
N/A |
$2693* |
Ports
- San Juan, Puerto Rico
- St. George's, Grenada
- Bequia, Grenadines
- Pigeon Island, 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.
- Spanish Town, Virgin Gorda, B.V.I.
Ports
San Juan, Puerto Rico - St. George's, Grenada - Bequia, Grenadines - Pigeon Island, 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. - Spanish Town, Virgin Gorda, B.V.I. - View more ports
| Partners | Bonus Offers | Inside | Oceanview | Balcony | Suite | |
|---|---|---|---|---|---|---|
|
|
N/A |
N/A |
N/A |
$4193* |
||
|
|
See Offers |
N/A |
N/A |
N/A |
$4193* |
|
|
|
N/A |
N/A |
N/A |
$4193* |
Ports
- San Juan, Puerto Rico
- St. George's, Grenada
- Bequia, Grenadines
- Pigeon Island, St. Lucia
- Terre-De-Haut, Iles Des Saintes, Guadeloupe
- Marigot, Saint Martin
Ports
San Juan, Puerto Rico - St. George's, Grenada - Bequia, Grenadines - Pigeon Island, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Marigot, Saint Martin - View more ports
| Partners | Bonus Offers | Inside | Oceanview | Balcony | Suite | |
|---|---|---|---|---|---|---|
|
|
N/A |
N/A |
N/A |
$2630* |
||
|
|
See Offers |
N/A |
N/A |
N/A |
$2693* |
|
|
|
N/A |
N/A |
N/A |
$2693* |
||
|
|
N/A |
N/A |
N/A |
$2630* |
||
|
|
See Offers |
N/A |
N/A |
N/A |
$2693* |
|
|
|
N/A |
N/A |
N/A |
$2693* |
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
- San Juan, Puerto Rico
- Gustavia, St. Barthelemy
- Basseterre, St. Kitts
- Philipsburg, St. Maarten
- Jost Van Dyke, B.V.I.
- Spanish Town, Virgin Gorda, B.V.I.
Ports
San Juan, Puerto Rico - Gustavia, St. Barthelemy - Basseterre, St. Kitts - 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 | |
|---|---|---|---|---|---|---|
|
|
N/A |
N/A |
N/A |
$2662* |
||
|
|
See Offers |
N/A |
N/A |
N/A |
$2662* |
|
|
|
N/A |
N/A |
N/A |
$2662* |
Ports
- Bridgetown, Barbados
- Little Bay, Montserrat
- Gustavia, St. Barthelemy
- Soper's Hole, Tortola, B.V.I.
- Jost Van Dyke, B.V.I.
- Spanish Town, Virgin Gorda, B.V.I.
- Terre-De-Haut, Iles Des Saintes, Guadeloupe
- Pigeon Island, St. Lucia
Ports
Bridgetown, Barbados - Little Bay, Montserrat - Gustavia, St. Barthelemy - Soper's Hole, Tortola, B.V.I. - Jost Van Dyke, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Pigeon Island, St. Lucia - View more ports
| Partners | Bonus Offers | Inside | Oceanview | Balcony | Suite | |
|---|---|---|---|---|---|---|
|
|
N/A |
$4077* |
N/A |
N/A |
||
|
|
See Offers |
N/A |
$4077* |
N/A |
N/A |
|
|
|
N/A |
$4077* |
N/A |
N/A |
All prices are per person based on double occupancy and do not include port/government fees and gratuities.