Cruise LineWindstar Cruises
ShipWind Surf
Nights14
DepartsSat, Dec 26th 2026
ReturnsSat, Jan 9th 2027
Departing PortPhilipsburg
Ports of CallPhilipsburg, Gustavia, Charlestown, Roseau, Mayreau, Pointe a Pitre, Basseterre, Philipsburg, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Philipsburg
Inside Cabin
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Outside
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Balcony
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Suite
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Itinerary
-
Day
Port
Arrive
Depart
-
Day 1
Arrival 1:00pm
Departure 7:00pm
-
Day 2
Port Gustavia
Arrival 8:00am
Departure 10:00pm
-
Day 3
Port Charlestown, Saint Kitts and Nevis
Arrival 8:00am
Departure 5:00pm
-
Day 4
Port Roseau, Dominica
Arrival 8:00am
Departure 4:00pm
-
Day 5
Port Mayreau, Saint Vincent and the Grenadines
Arrival 8:00am
Departure 5:00pm
-
Day 6
Port Pointe a Pitre, Guadeloupe
Arrival 12:00pm
Departure 6:00pm
-
Day 7
Port Basseterre, Saint Kitts and Nevis
Arrival 8:00am
Departure 10:00pm
-
Day 8
Arrival 6:00am
Departure 7:00pm
-
Day 9
Port Falmouth, Antigua and Barbuda
Arrival 8:00am
Departure 6:00pm
-
Day 10
Port Road Bay, Anguilla
Arrival 8:00am
Departure 6:00pm
-
Day 11
Port Tortola, British Virgin Islands
Arrival 8:00am
Departure 6:00pm
-
Day 11
Port Great Harbour, Jost Van Dyke BVI
Arrival 7:00pm
Departure --
-
Day 12
Port Great Harbour, Jost Van Dyke BVI
Arrival --
Departure 10:00pm
-
Day 13
Port Leverick Bay, Virgin Gorda, British Virgin Islands
Arrival 8:00am
Departure 5:00pm
-
Day 14
Port Gustavia
Arrival 8:00am
Departure 10:00pm
-
Day 15
Arrival 6:00am
Departure 7:00am
Ship Details
Ship Categories
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.