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
21 Night Caribbean - Extended Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 4th 2026
ReturnsSun, Jan 25th 2026
Nights21
Departing PortPhilpsburg
Ports of CallPhilpsburg, Falmouth, Road Bay, Sopers Hole, Great Harbour, Jost Van Dyke BVI (2 Days), Gustavia, Philpsburg, Basseterre, Gustavia, Terre-de-Haut, Mayreau, Kingstown, Bridgetown, Trois Ilets, Castries, Pigeon Island (2 Days), Port Elizabeth, Bequia, Mayreau, Saint George's, Bridgetown
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
14 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 4th 2026
ReturnsSun, Jan 18th 2026
Nights14
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
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
22 Night Caribbean - Extended Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 4th 2026
ReturnsMon, Jan 26th 2026
Nights22
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, Gustavia, Little Bay, Gustavia, Deshaies, Roseau, Pigeon Island, Bridgetown, Grande Anse, Castries, Pigeon Island, Admiralty Bay, Bequia, Mayreau, St. George's, Bridgetown
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
10 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Spirit
DepartsSun, Jan 4th 2026
ReturnsWed, Jan 14th 2026
Nights10
Departing PortBridgetown
Ports of CallBridgetown, Mayreau, Roseau, Trois Ilets, Deshaies, Basseterre, Falmouth, Gustavia, Road Bay, Philpsburg
With wide open, teak decks, the Wind Spirit is truly remarkable for a ship of its size. Plenty of spacious public places mean you can easily socialise with friends or just enjoy a quiet drink. Wind Spirit offers two primary dining venues. AmphorA Restaura…
Inside Cabin
Call for pricing
Ocean View
Call for pricing
Balcony
Call for pricing
Suite
Call for pricing
28 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 4th 2026
ReturnsSun, Feb 1st 2026
Nights28
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
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
7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 11th 2026
ReturnsSun, Jan 18th 2026
Nights7
Departing PortPhilipsburg
Ports of CallPhilipsburg, Basseterre, Little Bay, Gustavia, Deshaies, Roseau, Pigeon Island, Bridgetown
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
14 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 11th 2026
ReturnsSun, Jan 25th 2026
Nights14
Departing PortPhilipsburg
Ports of CallPhilipsburg, Basseterre, Little Bay, Gustavia, Deshaies, Roseau, Pigeon Island, Bridgetown, Grande Anse, Castries, Pigeon Island (2 Days), Admiralty Bay, Bequia, Mayreau, St. George's, Bridgetown
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
7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 18th 2026
ReturnsSun, Jan 25th 2026
Nights7
Departing PortBridgetown
Ports of CallBridgetown, Grande Anse, Castries, Pigeon Island (2 Days), Admiralty Bay, Bequia, Mayreau, St. George's, Bridgetown
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
14 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 18th 2026
ReturnsSun, Feb 1st 2026
Nights14
Departing PortBridgetown
Ports of CallBridgetown, 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
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
15 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 25th 2026
ReturnsMon, Feb 9th 2026
Nights15
Departing PortBridgetown
Ports of CallBridgetown, Man-O-War, Tobago, Mayreau, Soufriere Bay, Kralendijk, Bonaire, Willemstad, Oranjestad, Santa Marta, Cartagena, Bocas Del Toro, Colon (2 Days)
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
7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 25th 2026
ReturnsSun, Feb 1st 2026
Nights7
Departing PortBridgetown
Ports of CallBridgetown, Man-O-War, Tobago, Mayreau, Soufriere Bay, Kralendijk, Bonaire, Willemstad, Oranjestad
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
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.
