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Day 1: Philipsburg, St. Maarten
Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.
Itinerary at a Glance
Date
Port
Arrive
Depart
Watersports
PlatformWatersports Platform: 
Sat Feb 8
Philipsburg, St. Maarten
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Sun Feb 9
Charlestown
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Mon Feb 10
Roseau
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Tue Feb 11
Pigeon Island
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Wed Feb 12
Les Saintes
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Thu Feb 13
Basseterre
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Fri Feb 14
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sat Feb 15
Philipsburg, St. Maarten
Arrive:  6:00 AM
Depart:  7:00 PM
Watersports Platform: 
Sun Feb 16
Falmouth Harbour
Arrive:  8:00 AM
Depart:  1:00 PM
Watersports Platform: 
Mon Feb 17
Jost Van Dyke, Great Harbour
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Tue Feb 18
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Wed Feb 19
Soper's Hole
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Thu Feb 20
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Fri Feb 21
Road Bay
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Sat Feb 22
Philipsburg, St. Maarten
Arrive:  6:00 AM
Depart:  
Watersports Platform: 
Wind Surf
On any day, our 342-guest flagship, Wind Surf, the world’s largest sailing ship, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. During their cruise, you will find the perfect setting for ‘making an entrance’ in the beautiful reception area – and, appropriately, that’s only the beginning.
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Accommodations & Pricing
Boutique cruising with fewer than 350 guests. Our expertly designed itineraries and unexpected shore excursions bring you closer to each destination.
The Windstar Life
The Windstar staff-to-guest ratio is 1:1.5, and it shows.The moment you board you’ll feel it: an ever-attentive crew at your service, providing you with what you want and need, when you want and need it.
Friendly and Relaxed Atmosphere
Signature Onboard Barbecue
Cooking Demonstrations