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 $2,677 pp*
$382.43/night
Balcony
Call for pricing
Suite
From $3,517 pp*
$502.43/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 $5,510 pp*
$393.57/night
Balcony
Call for pricing
Suite
From $6,700 pp*
$478.57/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 $3,008 pp*
$429.71/night
Balcony
Call for pricing
Suite
From $3,848 pp*
$549.71/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 $6,280 pp*
$448.57/night
Balcony
Call for pricing
Suite
From $7,820 pp*
$558.57/night
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 $3,902 pp*
$557.43/night
Balcony
Call for pricing
Suite
From $4,742 pp*
$677.43/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 $6,280 pp*
$448.57/night
Balcony
Call for pricing
Suite
From $7,820 pp*
$558.57/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 $3,008 pp*
$429.71/night
Balcony
Call for pricing
Suite
From $3,848 pp*
$549.71/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 $5,790 pp*
$413.57/night
Balcony
Call for pricing
Suite
From $10,130 pp*
$723.57/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.
