7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Nov 2nd 2025
ReturnsSun, Nov 9th 2025
Nights7
Departing PortSan Juan
Ports of CallSan Juan, St. John Island, Basseterre, Gustavia, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan
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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Balcony
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Suite
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14 Night Caribbean - Extended Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Nov 2nd 2025
ReturnsSun, Nov 16th 2025
Nights14
Departing PortSan Juan
Ports of CallSan Juan, St. John Island, Basseterre, Gustavia, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan, St. George's, Admiralty Bay, Bequia, Pigeon Island, Pointe a Pitre, Marigot, San Juan
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…
Inside Cabin
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Ocean View
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Balcony
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Suite
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14 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Nov 9th 2025
ReturnsSun, Nov 23rd 2025
Nights14
Departing PortSan Juan
Ports of CallSan Juan, St. George's, Admiralty Bay, Bequia, Pigeon Island, Pointe a Pitre, Marigot, San Juan, St. John Island, Basseterre, Gustavia, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan
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…
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
ShipStar Pride
DepartsSat, Nov 15th 2025
ReturnsSat, Nov 22nd 2025
Nights7
Departing PortSan Juan
Ports of CallSan Juan, St. John Island, Philpsburg, Basseterre, Gustavia, Great Harbour, Jost Van Dyke BVI, Virgin Gorda, San Juan
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…
Inside Cabin
Call for pricing
Ocean View
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Balcony
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Suite
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14 Night Caribbean - Extended Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSat, Nov 15th 2025
ReturnsSat, Nov 29th 2025
Nights14
Departing PortSan Juan
Ports of CallSan Juan, St. John Island, Philpsburg, Basseterre, Gustavia, Great Harbour, Jost Van Dyke BVI, Virgin Gorda, San Juan, Saint George's, Port Elizabeth, Bequia, Pigeon Island, Iles Des Saintes, Philpsburg, San Juan
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…
Inside Cabin
Call for pricing
Ocean View
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Balcony
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Suite
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14 Night Caribbean - Extended Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Nov 16th 2025
ReturnsSun, Nov 30th 2025
Nights14
Departing PortSan Juan
Ports of CallSan Juan, St. John Island, Basseterre, Gustavia, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan, St. George's, Admiralty Bay, Bequia, Pigeon Island, Pointe a Pitre, Marigot, San Juan
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…
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
ShipStar Pride
DepartsSun, Nov 16th 2025
ReturnsSun, Nov 23rd 2025
Nights7
Departing PortSan Juan
Ports of CallSan Juan, St. John Island, Basseterre, Gustavia, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan
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…
Inside Cabin
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Ocean View
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Balcony
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Suite
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19 Night Mediterranean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsTue, Nov 18th 2025
ReturnsSun, Dec 7th 2025
Nights19
Departing PortLisbon
Ports of CallLisbon, Philipsburg, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, 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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Suite
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14 Night Caribbean - Extended Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Nov 23rd 2025
ReturnsSun, Dec 7th 2025
Nights14
Departing PortSan Juan
Ports of CallSan Juan, St. George's, Admiralty Bay, Bequia, Pigeon Island, Pointe a Pitre, Marigot, San Juan, St. John Island, Gustavia, Basseterre, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan
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…
Inside Cabin
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Ocean View
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Balcony
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Suite
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20 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Nov 30th 2025
ReturnsSat, Dec 20th 2025
Nights20
Departing PortSan Juan
Ports of CallSan Juan, St. John Island, Gustavia, Basseterre, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan, Santo Domingo, Cartagena (2 Days), San Blas, Colon, Exit Panama Canal, Balboa (2 Days), Isla Parida, Panama, Puerto Jimenez, Costa Rica, Puerto Quepos, Puerto Caldera
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…
Inside Cabin
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Ocean View
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Balcony
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Suite
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13 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Nov 30th 2025
ReturnsSat, Dec 13th 2025
Nights13
Departing PortSan Juan
Ports of CallSan Juan, St. John Island, Gustavia, Basseterre, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan, Santo Domingo, Cartagena (2 Days), San Blas, Colon
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…
Inside Cabin
Call for pricing
Ocean View
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Balcony
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Suite
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7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Nov 30th 2025
ReturnsSun, Dec 7th 2025
Nights7
Departing PortSan Juan
Ports of CallSan Juan, St. John Island, Gustavia, Basseterre, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan
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…
Inside Cabin
Call for pricing
Ocean View
Call for pricing
Balcony
Call for pricing
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.
