Ocean Crossings + Ponta Delgada, Azores
 
Philipsburg, St. Maarten to Lisbon
Sat Apr 4, 2026 - Sat Apr 18, 2026,
 14 days
 on Wind Surf
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Starting from $2,599 USD
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Philipsburg, St. Maarten to Lisbon
This is a place where dreams really do come true. The place where nothing comes between you and your fondest wishes. Where no schedules intrude, where day-to-day annoyances can’t reach you, where every moment of every hour of every day is yours alone. This is your place – at sea under an open sky – the one place in which you truly can get away from it all. Simply step on board and we’ll take it from there. Meals so delicious they might be sinful are served when, where, and any way you choose. Decadent spa treatments. Lazy hours stretched out on deck. Workouts you’ve been meaning to get around to in the state-of-the-art Fitness Center. Uninterrupted time to spend with new friends or in exquisite solitude. One delightful stop in Ponta Delgada, the Azores Islands en route to Lisbon for an outdoor activity or relaxing on the beach.  Best of all, this is the place and the time to reconnect – with each other, with yourself, with your dreams.
voyage map
Popular Highlights
Bridge
Drop by the Bridge for an impromptu navigation lesson.
Friends
Make new friendships with like-minded travelers Savor extraordinary cuisine then use the great fitness equipment to work it off.
Massage
Find you have time for your favorite indulgences – from a relaxing massage to breakfast in bed.
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Sat Apr 4
Philipsburg, St. Maarten
Arrive:  
Depart:  7:00 PM
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Sun Apr 5
AT SEA
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Mon Apr 6
AT SEA
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Tue Apr 7
AT SEA
Arrive:  
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Wed Apr 8
AT SEA
Arrive:  
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Thu Apr 9
AT SEA
Arrive:  
Depart:  
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Fri Apr 10
AT SEA
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Sat Apr 11
AT SEA
Arrive:  
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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
Arrive:  
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Fri Apr 17
AT SEA
Arrive:  
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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.
Category B
Category B
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Cruise only from $2,599 per guest
? All-inclusive price from $3,985 per guest
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
ALL DATES &
FARES
Last Minute Cruise Deals
Pick Your Perk
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited select beer, wine, and cocktails, and gratuities. From $99 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sat, Mar 29 - Sat, Apr 12, 2025
WIND SURF
$3,274
$1,888
Sat, Apr 4 - Sat, Apr 18, 2026
WIND SURF
$3,985
$2,599
THIS
SAILING