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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
MarinaWatersports Platform: 
Sat Apr 4
Philipsburg, St. Maarten
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Sun Apr 5
AT SEA
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Mon Apr 6
AT SEA
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Tue Apr 7
AT SEA
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Wed Apr 8
AT SEA
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Thu Apr 9
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Apr 10
AT SEA
Arrive:  
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Sat Apr 11
AT SEA
Arrive:  
Depart:  
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Sun Apr 12
AT SEA
Arrive:  
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Mon Apr 13
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Tue Apr 14
Ponta Delgada
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Apr 15
AT SEA
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Depart:  
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Thu Apr 16
AT SEA
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Depart:  
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Fri Apr 17
AT SEA
Arrive:  
Depart:  
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Sat Apr 18
Lisbon
Arrive:  7:00 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