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Windstar Cruises — Wind Surf

FROM
$16999

Departure: 1/4/2026

Length: 55 Nights

Ports: St. Maarten (Philipsburg) | Falmouth Harbour, Antigua | Road Bay | Sopers Hole, Tortola | Jost Van Dyke | Jost Van Dyke | Virgin Gorda | Gustavia | St. Maarten (Philipsburg) | Basseterre, St. Kitts | Little Bay | Gustavia | Deshaies, Guadeloupe | Roseau, Dominica | Pigeon Island, St. Lucia | Bridgetown (Barbados) | Anse Mitan | Castries | Pigeon Island, St. Lucia | Pigeon Island, St. Lucia | Bequia, Grenadines | Mayreau, Grenadines | St. George's, Grenada | Bridgetown (Barbados) | Man O'War Bay, Tobago | Mayreau, Grenadines | Soufriere | Kralendijk | Willemstad, Curacao | Oranjestad, Aruba | Santa Marta | Cartagena (Colombia) | Bocas del Toro | Colon (Panama) | Colon (Panama) | Bocas del Toro | San Andres Island | Roatan Island | Belize City | Costa Maya | Cozumel | Grand Cayman (George Town) | Cayman Brac | Port Antonio | Santo Domingo | Casa de Campo | Jost Van Dyke | Virgin Gorda | St. Maarten (Philipsburg) |


Offer ID #: 1512967   |   Compare This Offer

Windstar Cruises — Wind Surf

FROM
$5599

Departure: 2/9/2026

Length: 19 Nights

Ports: Colon (Panama) | Bocas del Toro | San Andres Island | Roatan Island | Belize City | Costa Maya | Cozumel | Grand Cayman (George Town) | Cayman Brac | Port Antonio | Santo Domingo | Casa de Campo | Jost Van Dyke | Virgin Gorda | St. Maarten (Philipsburg) |


Offer ID #: 1512976   |   Compare This Offer

Windstar Cruises — Wind Surf

FROM
$3799

Departure: 2/17/2026

Length: 11 Nights

Ports: Cozumel | Grand Cayman (George Town) | Cayman Brac | Port Antonio | Santo Domingo | Casa de Campo | Jost Van Dyke | Virgin Gorda | St. Maarten (Philipsburg) |


The Signature Collection – Exclusive Amenities

Exclusive Amenities

Offer ID #: 1512977   |   Compare This Offer

Windstar Cruises — Wind Surf

FROM
$4799

Departure: 2/17/2026

Length: 18 Nights

Ports: Cozumel | Grand Cayman (George Town) | Cayman Brac | Port Antonio | Santo Domingo | Casa de Campo | Jost Van Dyke | Virgin Gorda | St. Maarten (Philipsburg) | Charlestown | Roseau, Dominica | Pigeon Island, St. Lucia | Iles des Saintes | Gustavia | Basseterre, St. Kitts | St. Maarten (Philipsburg) |


The Signature Collection – Exclusive Amenities

Exclusive Amenities

Offer ID #: 1512978   |   Compare This Offer

Windstar Cruises — Star Pride

FROM
$4399

Departure: 11/29/2025

Length: 14 Nights

Ports: San Juan | St. John (U.S.V.I.) | St. Maarten (Philipsburg) | Basseterre, St. Kitts | Gustavia | Jost Van Dyke | Virgin Gorda | San Juan | Catalina Island/Casa de Campo | Santo Domingo | Cartagena (Colombia) | Cartagena (Colombia) | San Blas Islands | Colon (Panama) |


Offer ID #: 1521042   |   Compare This Offer

Windstar Cruises — Star Pride

FROM
$6799

Departure: 11/29/2025

Length: 21 Nights

Ports: San Juan | St. John (U.S.V.I.) | St. Maarten (Philipsburg) | Basseterre, St. Kitts | Gustavia | Jost Van Dyke | Virgin Gorda | San Juan | Catalina Island/Casa de Campo | Santo Domingo | Cartagena (Colombia) | Cartagena (Colombia) | San Blas Islands | Colon (Panama) | Panama Canal | Balboa | Balboa | Isla Parida | Golfo Dulce (Puerto Jimenez) | Quepos | Puntarenas |


Offer ID #: 1512797   |   Compare This Offer

Windstar Cruises — Star Pride

FROM
$4099

Departure: 12/6/2025

Length: 14 Nights

Ports: San Juan | Catalina Island/Casa de Campo | Santo Domingo | Cartagena (Colombia) | Cartagena (Colombia) | San Blas Islands | Colon (Panama) | Panama Canal | Balboa | Balboa | Isla Parida | Golfo Dulce (Puerto Jimenez) | Quepos | Puntarenas |


The Signature Collection – Exclusive Amenities

Exclusive Amenities

Offer ID #: 1512798   |   Compare This Offer

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