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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
$8599

Departure: 1/4/2026

Length: 28 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 |


Offer ID #: 1525847   |   Compare This Offer

Windstar Cruises — Star Pride

CALL

Departure: 10/7/2025

Length: 22 Nights

Ports: Montreal | Quebec City | Quebec City | Gaspe | Cap-aux-Meules | Louisbourg | Halifax (Nova Scotia) | Lunenburg (Nova Scotia) | Bar Harbor | Portland, ME | Boston | Hamilton | Hamilton | St. George's, Bermuda | St. George's, Bermuda | Gustavia | Basseterre, St. Kitts | Virgin Gorda | San Juan |


The Signature Collection – Exclusive Amenities

Exclusive Amenities

Offer ID #: 1502782   |   Compare This Offer

Windstar Cruises — Star Pride

FROM
$5799

Departure: 10/12/2024

Length: 22 Nights

Ports: Montreal | Quebec City | Quebec City | Gaspe | Cap-aux-Meules | Louisbourg | Halifax (Nova Scotia) | Portland, ME | Portland, ME | Boston | Hamilton | Hamilton | St. George's, Bermuda | St. George's, Bermuda | Gustavia | Basseterre, St. Kitts | Virgin Gorda | San Juan |


Offer ID #: 1489169   |   Compare This Offer

Windstar Cruises — Wind Surf

FROM
$5899

Departure: 3/30/2024

Length: 22 Nights

Ports: St. Maarten (Philipsburg) | Ponta Delgada (Azores) | Lisbon | Seville (Cadiz) | Gibraltar | Malaga | Almeria | Cartagena (Spain) | Palma de Mallorca | Barcelona |


Offer ID #: 1489466   |   Compare This Offer

Windstar Cruises — Wind Surf

FROM
$4899

Departure: 3/29/2025

Length: 22 Nights

Ports: St. Maarten (Philipsburg) | Ponta Delgada (Azores) | Lisbon | Seville (Cadiz) | Gibraltar | Malaga | Almeria | Cartagena (Spain) | Palma de Mallorca | Barcelona |


Offer ID #: 1502911   |   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

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