55 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 4th 2026
ReturnsSat, Feb 28th 2026
Nights55
Departing PortPhilipsburg
Ports of CallPhilipsburg, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Philipsburg, Basseterre, Little Bay, Gustavia, Pointe a Pitre, Roseau, Pigeon Island, Bridgetown, Grande Anse, Castries, Pigeon Island (2 Days), Admiralty Bay, Bequia, Mayreau, St. George's, Bridgetown, Man-O-War, Tobago, Mayreau, Soufriere Bay, Kralendijk, Bonaire, Willemstad, Oranjestad, Santa Marta, Cartagena, Bocas Del Toro, Colon (2 Days), Bocas Del Toro, San Andres Island, Roatan, Belize City, Puerto Costa Maya, Mexico, Cozumel, Grand Cayman, Cayman Brac, Port Antonio, Santo Domingo, La Romana, Great Harbour, Jost Van Dyke BVI, 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
Ocean View
Call for pricing
Balcony
Call for pricing
Suite
Call for pricing
8 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipStar Seeker
DepartsThu, Jan 15th 2026
ReturnsFri, Jan 23rd 2026
Nights8
Departing PortMiami
Ports of CallMiami, Puerto Plata, Santo Domingo, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, Tortola, San Juan
Coming Dec. 2025, Star Seeker will be our first-ever Star Class new build, followed by Star Explorer in Dec. 2026. Serving 224 guests, each ship will feature 112 suites with full private verandas and infinity windows. They’ll also com…
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.
