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
Call for pricing
Ocean View
Call for pricing
Balcony
Call for pricing
Suite
Call for pricing
7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Nov 9th 2025
ReturnsSun, Nov 16th 2025
Nights7
Departing PortSan Juan
Ports of CallSan 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
Call for pricing
Ocean View
Call for pricing
Balcony
Call for pricing
Suite
Call for pricing
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
Call for pricing
Ocean View
Call for pricing
Balcony
Call for pricing
Suite
Call for pricing
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
Call for pricing
Ocean View
Call for pricing
Balcony
Call for pricing
Suite
Call for pricing
7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Nov 23rd 2025
ReturnsSun, Nov 30th 2025
Nights7
Departing PortSan Juan
Ports of CallSan 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
Call for pricing
Ocean View
Call for pricing
Balcony
Call for pricing
Suite
Call for pricing
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.
