14 Night Caribbean - Extended Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Nov 8th 2026
ReturnsSun, Nov 22nd 2026
Nights14
Departing PortSan Juan
Ports of CallSan Juan, St. George's, Admiralty Bay, Bequia, Mayreau, Pointe a Pitre, Marigot Bay, 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
Outside
Call for pricing
Balcony
Call for pricing
Suite
From $15,214 pp*
$1,086.71/night
7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Nov 8th 2026
ReturnsSun, Nov 15th 2026
Nights7
Departing PortSan Juan
Ports of CallSan Juan, St. George's, Admiralty Bay, Bequia, Mayreau, Pointe a Pitre, 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 $3,181 pp*
$454.43/night
Balcony
From $5,561 pp*
$794.43/night
Suite
From $8,921 pp*
$1,274.43/night
7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Nov 15th 2026
ReturnsSun, Nov 22nd 2026
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
Call for pricing
Outside
From $5,663 pp*
$809.00/night
Balcony
Call for pricing
Suite
From $7,903 pp*
$1,129.00/night
14 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Nov 15th 2026
ReturnsSun, Nov 29th 2026
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, Mayreau, Pointe a Pitre, 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
Call for pricing
Suite
From $12,834 pp*
$916.71/night
7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Nov 22nd 2026
ReturnsSun, Nov 29th 2026
Nights7
Departing PortSan Juan
Ports of CallSan Juan, St. George's, Admiralty Bay, Bequia, Mayreau, Pointe a Pitre, 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 $2,691 pp*
$384.43/night
Balcony
From $3,531 pp*
$504.43/night
Suite
From $4,511 pp*
$644.43/night
14 Night Caribbean - Extended Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Nov 22nd 2026
ReturnsSun, Dec 6th 2026
Nights14
Departing PortSan Juan
Ports of CallSan Juan, St. George's, Admiralty Bay, Bequia, Mayreau, Pointe a Pitre, 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
From $8,144 pp*
$581.71/night
Suite
From $10,244 pp*
$731.71/night
14 Night Caribbean - Extended Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Nov 29th 2026
ReturnsSun, Dec 13th 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 $9,614 pp*
$686.71/night
Suite
From $10,524 pp*
$751.71/night
7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipStar Pride
DepartsSun, Nov 29th 2026
ReturnsSun, Dec 6th 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
Call for pricing
Balcony
From $5,453 pp*
$779.00/night
Suite
From $5,943 pp*
$849.00/night
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.
