7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Dec 19th 2026
ReturnsSat, Dec 26th 2026
Nights7
Departing PortPhilipsburg
Ports of CallPhilipsburg, Gustavia, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), 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,… 
Inside Cabin
Call for pricing
Outside
From $3,255 pp*
$465.00/night
Balcony
Call for pricing
Suite
From $3,780 pp*
$540.00/night
14 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Dec 19th 2026
ReturnsSat, Jan 2nd 2027
Nights14
Departing PortPhilipsburg
Ports of CallPhilipsburg, Gustavia, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Philipsburg, Gustavia, Charlestown, Roseau, Mayreau, Pointe a Pitre, Basseterre, 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,…
Inside Cabin
Call for pricing
Outside
From $5,320 pp*
$380.00/night
Balcony
Call for pricing
Suite
From $6,160 pp*
$440.00/night
7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Dec 26th 2026
ReturnsSat, Jan 2nd 2027
Nights7
Departing PortPhilipsburg
Ports of CallPhilipsburg, Gustavia, Charlestown, Roseau, Mayreau, Pointe a Pitre, Basseterre, 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,…
Inside Cabin
Call for pricing
Outside
From $3,045 pp*
$435.00/night
Balcony
Call for pricing
Suite
From $3,710 pp*
$530.00/night
14 Night Caribbean - Extended Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Dec 26th 2026
ReturnsSat, Jan 9th 2027
Nights14
Departing PortPhilipsburg
Ports of CallPhilipsburg, Gustavia, Charlestown, Roseau, Mayreau, Pointe a Pitre, Basseterre, Philipsburg, Falmouth, Road Bay, Anguilla, 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,…
Inside Cabin
Call for pricing
Outside
From $5,936 pp*
$424.00/night
Balcony
Call for pricing
Suite
From $6,804 pp*
$486.00/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.
