7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Feb 6th 2027
ReturnsSat, Feb 13th 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
Outside
From $4,427 pp*
$632.43/night
Balcony
Call for pricing
Suite
From $5,267 pp*
$752.43/night
14 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Feb 6th 2027
ReturnsSat, Feb 20th 2027
Nights14
Departing PortPhilipsburg
Ports of CallPhilipsburg, Charlestown, Roseau, Mayreau, Pointe a Pitre, Basseterre, Gustavia, 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 $6,840 pp*
$488.57/night
Balcony
Call for pricing
Suite
From $8,380 pp*
$598.57/night
7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Feb 13th 2027
ReturnsSat, Feb 20th 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
Call for pricing
Outside
From $3,113 pp*
$444.71/night
Balcony
Call for pricing
Suite
From $3,953 pp*
$564.71/night
14 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Feb 13th 2027
ReturnsSat, Feb 27th 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, 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
Outside
From $5,930 pp*
$423.57/night
Balcony
Call for pricing
Suite
Call for pricing
7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Feb 20th 2027
ReturnsSat, Feb 27th 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
Outside
From $3,412 pp*
$487.43/night
Balcony
Call for pricing
Suite
From $4,252 pp*
$607.43/night
14 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Feb 20th 2027
ReturnsSat, Mar 6th 2027
Nights14
Departing PortPhilipsburg
Ports of CallPhilipsburg, Charlestown, Roseau, Mayreau, Pointe a Pitre, Basseterre, Gustavia, Philipsburg, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Road Bay, Anguilla, 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
Outside
From $6,000 pp*
$428.57/night
Balcony
Call for pricing
Suite
From $7,470 pp*
$533.57/night
7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Feb 27th 2027
ReturnsSat, Mar 6th 2027
Nights7
Departing PortPhilipsburg
Ports of CallPhilipsburg, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Road Bay, Anguilla, 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
Outside
From $3,148 pp*
$449.71/night
Balcony
Call for pricing
Suite
From $3,988 pp*
$569.71/night
14 Night Caribbean - Extended Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Feb 27th 2027
ReturnsSat, Mar 13th 2027
Nights14
Departing PortPhilipsburg
Ports of CallPhilipsburg, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Road Bay, Anguilla, 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
Outside
From $6,070 pp*
$433.57/night
Balcony
Call for pricing
Suite
From $7,330 pp*
$523.57/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.
