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
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Outside
From $6,840 pp*
$488.57/night
Balcony
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Suite
From $7,820 pp*
$558.57/night
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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Outside
From $3,568 pp*
$509.71/night
Balcony
Call for pricing
Suite
From $4,093 pp*
$584.71/night
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
Outside
From $3,657 pp*
$522.43/night
Balcony
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Suite
From $4,497 pp*
$642.43/night
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
Outside
From $7,960 pp*
$568.57/night
Balcony
Call for pricing
Suite
From $8,450 pp*
$603.57/night
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
Outside
From $3,708 pp*
$529.71/night
Balcony
Call for pricing
Suite
From $4,373 pp*
$624.71/night
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
Outside
From $8,380 pp*
$598.57/night
Balcony
Call for pricing
Suite
Call for pricing
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
Outside
From $4,917 pp*
$702.43/night
Balcony
Call for pricing
Suite
From $8,557 pp*
$1,222.43/night
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
Outside
From $7,750 pp*
$553.57/night
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
Outside
From $3,183 pp*
$454.71/night
Balcony
Call for pricing
Suite
From $4,023 pp*
$574.71/night
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
Outside
From $6,910 pp*
$493.57/night
Balcony
Call for pricing
Suite
From $8,450 pp*
$603.57/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.
