14 Night Caribbean - Extended Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Dec 6th 2026
ReturnsSun, Dec 20th 2026
Nights14
Departing PortSan Juan
Ports of CallSan Juan, St. George's, Admiralty Bay, Bequia, Mayreau, Deshaies, Marigot Bay, 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
Outside
From $5,834 pp*
$416.71/night
Balcony
From $7,654 pp*
$546.71/night
Suite
Call for pricing
7 Night Caribbean - Southern Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Dec 6th 2026
ReturnsSun, Dec 13th 2026
Nights7
Departing PortSan Juan
Ports of CallSan Juan, St. George's, Admiralty Bay, Bequia, Mayreau, Deshaies, Marigot Bay, 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
Outside
From $2,866 pp*
$409.43/night
Balcony
From $3,776 pp*
$539.43/night
Suite
From $7,836 pp*
$1,119.43/night
7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Dec 13th 2026
ReturnsSun, Dec 20th 2026
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
Outside
From $3,213 pp*
$459.00/night
Balcony
From $4,193 pp*
$599.00/night
Suite
From $4,683 pp*
$669.00/night
14 Night Caribbean - Extended Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Dec 13th 2026
ReturnsSun, Dec 27th 2026
Nights14
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, St. George's, Admiralty Bay, Bequia, Mayreau, Deshaies, Marigot Bay, 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
Outside
Call for pricing
Balcony
From $8,984 pp*
$641.71/night
Suite
From $12,204 pp*
$871.71/night
14 Night Caribbean - Extended Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Dec 20th 2026
ReturnsSun, Jan 3rd 2027
Nights14
Departing PortSan Juan
Ports of CallSan Juan, St. George's, Admiralty Bay, Bequia, Mayreau, Deshaies, Marigot Bay, 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
Outside
Call for pricing
Balcony
Call for pricing
Suite
Call for pricing
7 Night Caribbean - Southern Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Dec 20th 2026
ReturnsSun, Dec 27th 2026
Nights7
Departing PortSan Juan
Ports of CallSan Juan, St. George's, Admiralty Bay, Bequia, Mayreau, Deshaies, Marigot Bay, 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
Outside
From $3,881 pp*
$554.43/night
Balcony
From $5,526 pp*
$789.43/night
Suite
From $7,101 pp*
$1,014.43/night
14 Night Caribbean - Extended Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Dec 27th 2026
ReturnsSun, Jan 10th 2027
Nights14
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, St. George's, Admiralty Bay, Bequia, Mayreau, Deshaies, Marigot Bay, 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
Outside
From $7,374 pp*
$526.71/night
Balcony
Call for pricing
Suite
Call for pricing
7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Dec 27th 2026
ReturnsSun, Jan 3rd 2027
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
Outside
From $4,823 pp*
$689.00/night
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.
