7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Jan 2nd 2027
ReturnsSat, Jan 9th 2027
Nights7
Departing PortPhilipsburg
Ports of CallPhilipsburg, 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
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Ocean View
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Balcony
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Suite
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14 Night Caribbean - Extended Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Jan 2nd 2027
ReturnsSat, Jan 16th 2027
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, Charlestown, Pointe a Pitre, Mayreau, Roseau, Basseterre, 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
Ocean View
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Balcony
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Suite
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7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Jan 9th 2027
ReturnsSat, Jan 16th 2027
Nights7
Departing PortPhilipsburg
Ports of CallPhilipsburg, Charlestown, Pointe a Pitre, Mayreau, Roseau, Basseterre, 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
Ocean View
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Balcony
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Suite
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14 Night Caribbean - Extended Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Jan 9th 2027
ReturnsSat, Jan 23rd 2027
Nights14
Departing PortPhilipsburg
Ports of CallPhilipsburg, Charlestown, Pointe a Pitre, Mayreau, Roseau, Basseterre, Gustavia, Philipsburg, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Falmouth, 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
7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Jan 16th 2027
ReturnsSat, Jan 23rd 2027
Nights7
Departing PortPhilipsburg
Ports of CallPhilipsburg, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Falmouth, 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
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Balcony
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Suite
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14 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Jan 16th 2027
ReturnsSat, Jan 30th 2027
Nights14
Departing PortPhilipsburg
Ports of CallPhilipsburg, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Falmouth, Philipsburg, Charlestown, Roseau, Mayreau, Pointe a Pitre, Basseterre, 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
Ocean View
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Balcony
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Suite
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8 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsMon, Jan 18th 2027
ReturnsTue, Jan 26th 2027
Nights8
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
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Ocean View
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Balcony
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Suite
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7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Jan 23rd 2027
ReturnsSat, Jan 30th 2027
Nights7
Departing PortPhilipsburg
Ports of CallPhilipsburg, Charlestown, Roseau, Mayreau, Pointe a Pitre, Basseterre, 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
Ocean View
Call for pricing
Balcony
Call for pricing
Suite
Call for pricing
14 Night Caribbean - Extended Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Jan 23rd 2027
ReturnsSat, Feb 6th 2027
Nights14
Departing PortPhilipsburg
Ports of CallPhilipsburg, Charlestown, Roseau, Mayreau, Pointe a Pitre, Basseterre, Gustavia, Philipsburg, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Falmouth, 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
7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Jan 30th 2027
ReturnsSat, Feb 6th 2027
Nights7
Departing PortPhilipsburg
Ports of CallPhilipsburg, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Falmouth, 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
14 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Jan 30th 2027
ReturnsSat, Feb 13th 2027
Nights14
Departing PortPhilipsburg
Ports of CallPhilipsburg, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Falmouth, Philipsburg, Charlestown, Roseau, Mayreau, Pointe a Pitre, Basseterre, 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
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.
