Ocean Crossings + Ponta Delgada, Azores
 
Philipsburg, St. Maarten to Lisbon
Sat Mar 29, 2025 - Sat Apr 12, 2025,
 14 days
 on Wind Surf
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Starting from $1,818 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 Mar 29
Philipsburg, St. Maarten
Arrive:  
Depart:  7:00 PM
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Sun Mar 30
AT SEA
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Mon Mar 31
AT SEA
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Tue Apr 1
AT SEA
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Wed Apr 2
AT SEA
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Thu Apr 3
AT SEA
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Fri Apr 4
AT SEA
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Sat Apr 5
AT SEA
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Sun Apr 6
AT SEA
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Mon Apr 7
AT SEA
Arrive:  
Depart:  
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Tue Apr 8
Ponta Delgada
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Apr 9
AT SEA
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Thu Apr 10
AT SEA
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Fri Apr 11
AT SEA
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Sat Apr 12
Lisbon
Arrive:  7:00 AM
Depart:  
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Accommodations & Pricing
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 $1,818 per guest
? All-inclusive price from $3,204 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
$3,204
$1,818
THIS
SAILING
Sat, Apr 4 - Sat, Apr 18, 2026
WIND SURF
$3,985
$2,599