Ocean Crossings

 
Lisbon to Philipsburg, St. Maarten
Sat Dec 5, 2026 - Sat Dec 19, 2026,
 14 days
 on Wind Surf
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Starting from $2,499 USD
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Lisbon to Philipsburg, St. Maarten
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. 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
Dropping by the Bridge for an impromptu navigation lesson.
cuisine
Extraordinary cuisine – and great fitness equipment to work it off.
Friends
New friendships with like-minded travelers.
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Sat Dec 5
Lisbon
Arrive:  
Depart:  5:00 PM
Watersports Platform: 
Sun Dec 6
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Mon Dec 7
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Tue Dec 8
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Wed Dec 9
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Thu Dec 10
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Dec 11
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sat Dec 12
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sun Dec 13
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Mon Dec 14
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Tue Dec 15
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Wed Dec 16
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Thu Dec 17
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Dec 18
St. John's
Arrive:  8:00 AM
Depart:  7:00 PM
Watersports Platform: 
Sat Dec 19
Philipsburg, St. Maarten
Arrive:  6:00 AM
Depart:  
Watersports Platform: 
Accommodations & Pricing
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar) 
? Call for Availability
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
2026 & 2027 Early Booking Offer
Go All-Inclusive — On Us
Ways to Winter Sales Event
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
Sun, Mar 22 - Tue, Apr 7, 2026
STAR PRIDE
$3,099
$3,099
Tue, Apr 28 - Wed, May 6, 2026
STAR SEEKER
$2,991
$2,199
Wed, Sep 2 - Wed, Sep 16, 2026
STAR SEEKER
$4,585
$3,199
Sat, Dec 5 - Sat, Dec 19, 2026
WIND SURF
$2,499
$2,499
THIS
SAILING
Mon, Feb 8 - Mon, Mar 1, 2027
WIND STAR
$3,799
$3,799
Sat, Mar 27 - Sun, Apr 11, 2027
WIND SURF
$2,799
$2,799