55 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 4th 2026
ReturnsSat, Feb 28th 2026
Nights55
Departing PortPhilipsburg
Ports of CallPhilipsburg, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Philipsburg, Basseterre, Little Bay, Gustavia, Pointe a Pitre, Roseau, Pigeon Island, Bridgetown, Grande Anse, Castries, Pigeon Island (2 Days), Admiralty Bay, Bequia, Mayreau, St. George's, Bridgetown, Man-O-War, Tobago, Mayreau, Soufriere Bay, Kralendijk, Bonaire, Willemstad, Oranjestad, Santa Marta, Cartagena, Bocas Del Toro, Colon (2 Days), Bocas Del Toro, San Andres Island, Roatan, Belize City, Puerto Costa Maya, Mexico, Cozumel, Grand Cayman, Cayman Brac, Port Antonio, Santo Domingo, La Romana, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, Philipsburg
On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms,… 
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28 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 4th 2026
ReturnsSun, Feb 1st 2026
Nights28
Departing PortPhilipsburg
Ports of CallPhilipsburg, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Philipsburg, Basseterre, Little Bay, Gustavia, Pointe a Pitre, Roseau, Pigeon Island, Bridgetown, Grande Anse, Castries, Pigeon Island (2 Days), Admiralty Bay, Bequia, Mayreau, St. George's, Bridgetown, Man-O-War, Tobago, Mayreau, Soufriere Bay, Kralendijk, Bonaire, Willemstad, Oranjestad
On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms,…
Inside Cabin
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Ocean View
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Balcony
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Suite
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6 Night Panama Canal Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Jan 11th 2026
ReturnsSat, Jan 17th 2026
Nights6
Departing PortBalboa
Ports of CallBalboa, Exit Panama Canal, Bocas Del Toro, San Blas, Cartagena, Oranjestad
All Suite Ship
Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…
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8 Night Panama Canal Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSat, Jan 17th 2026
ReturnsSun, Jan 25th 2026
Nights8
Departing PortOranjestad
Ports of CallOranjestad, Cartagena (2 Days), Bocas Del Toro, San Blas, Exit Panama Canal, Balboa
All Suite Ship
Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…
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Ocean View
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14 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 18th 2026
ReturnsSun, Feb 1st 2026
Nights14
Departing PortBridgetown
Ports of CallBridgetown, Grande Anse, Castries, Pigeon Island (2 Days), Admiralty Bay, Bequia, Mayreau, St. George's, Bridgetown, Man-O-War, Tobago, Mayreau, Soufriere Bay, Kralendijk, Bonaire, Willemstad, Oranjestad
On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms,…
Inside Cabin
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Ocean View
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Balcony
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Suite
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15 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 25th 2026
ReturnsMon, Feb 9th 2026
Nights15
Departing PortBridgetown
Ports of CallBridgetown, Man-O-War, Tobago, Mayreau, Soufriere Bay, Kralendijk, Bonaire, Willemstad, Oranjestad, Santa Marta, Cartagena, Bocas Del Toro, Colon (2 Days)
On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms,…
Inside Cabin
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Ocean View
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Balcony
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Suite
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7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 25th 2026
ReturnsSun, Feb 1st 2026
Nights7
Departing PortBridgetown
Ports of CallBridgetown, Man-O-War, Tobago, Mayreau, Soufriere Bay, Kralendijk, Bonaire, Willemstad, Oranjestad
On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all new finishes and furnishings in suites and staterooms,…
Inside Cabin
Call for pricing
Ocean View
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Balcony
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Suite
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Prices are per person, double occupancy, cruise only and on select sailings. Prices shown are for stateroom categories as noted and are shown in US Dollars. Pricing listed includes taxes and fees. Airfare is not included. Prices and itineraries are based on availability and are subject to change without notice.
