Ocean Crossings
 
Lisbon to Philipsburg, St. Maarten
Sat Dec 7, 2024 - Sat Dec 21, 2024,
 14 days
 on Wind Surf
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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
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Day 1: Lisbon
The rhythm of Lisbon invites you to join its captivating dance. This splendid capital city on the banks of the Rio Teja offers a warm welcome and an unparalleled blend of architectural styles. Elegant outdoor cafés line the cobbled sidewalks. Turn-of-the-century funiculars climb the scenic hills. Find the UNESCO sites of the Tower of Belem and the Monastery of the Hieronymites. And, everywhere, the city engages you with its easy style and remarkable charm.
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Day 14: St. John's
St. John’s is a city of Old World charm and elegance which lingers in the varied architecture of Georgian, Victorian, Vernacular, Romantic and International flavors.  The picturesque seafront where tiny, colorful boats are moored, the cheerful wooden buildings carefully refurbished to retain their original features, the vibrant Market Street offering vegetables, fruit and fish and the duty-free Heritage Quay shopping area provide a delightful atmosphere to captivate you.  Sites to see include St. John’s Cathedral with its white Baroque towers, the Botanical Garden, St. John’s Antigua Lighthouse, and Fort James.
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Day 15: 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.
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.
Massage
Time for your favorite indulgences – from a relaxing massage to breakfast in bed.
Private yacht lifestyle
Private yacht lifestyle with no interruptions.
stars overhead
More stars overhead than you ever imagined.
vistas from your stateroom
Sweeping ocean vistas from your stateroom or suite.
Itinerary at a Glance
Date
Port
Arrive
Depart
Watersports
PlatformWatersports Platform: 
Sat Dec 7
Lisbon
Arrive:  
Depart:  5:00 PM
Watersports Platform: 
Sun Dec 8
AT SEA
Arrive:  
Depart:  
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Mon Dec 9
AT SEA
Arrive:  
Depart:  
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Tue Dec 10
AT SEA
Arrive:  
Depart:  
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Wed Dec 11
AT SEA
Arrive:  
Depart:  
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Thu Dec 12
AT SEA
Arrive:  
Depart:  
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Fri Dec 13
AT SEA
Arrive:  
Depart:  
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Sat Dec 14
AT SEA
Arrive:  
Depart:  
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Sun Dec 15
AT SEA
Arrive:  
Depart:  
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Mon Dec 16
AT SEA
Arrive:  
Depart:  
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Tue Dec 17
AT SEA
Arrive:  
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Wed Dec 18
AT SEA
Arrive:  
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Thu Dec 19
AT SEA
Arrive:  
Depart:  
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Fri Dec 20
St. John's
Arrive:  8:00 AM
Depart:  7:00 PM
Watersports Platform: 
Sat Dec 21
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
Genuine and Thoughtful Crew
Crew Talent Show
Open Bridge
Local and Live Performances
Relax at the Pool or Hot Tub
Complimentary 24 Hour Room Service
Signature Sail Away
Shopping With The Chef
Take In The Sun
Watersports Platform
Enjoy regionally inspired treatments at World Spa by Windstar
Relax With A Morning Yoga Session
ALL DATES &
FARES
Complimentary All-Inclusive Upgrade
Early Booking Offer 2026
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited beer, wine, and cocktails, and gratuities. From $89 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Tue, Nov 5 - Tue, Nov 19, 2024
WIND STAR
$2,199
$2,199
Wed, Nov 13 - Wed, Nov 27, 2024
WIND SPIRIT
$2,499
$2,499
Sat, Dec 7 - Sat, Dec 21, 2024
WIND SURF
Call For Availability
THIS
SAILING
Thu, Jan 2 - Thu, Jan 16, 2025
STAR BREEZE
$1,999
$1,999
Sun, Feb 2 - Sun, Feb 16, 2025
STAR BREEZE
$1,999
$1,999
Sat, Feb 22 - Sun, Mar 9, 2025
WIND SPIRIT
$2,399
$2,399
Wed, Mar 26 - Thu, Apr 10, 2025
WIND STAR
$2,399
$2,399
Sat, Apr 5 - Tue, Apr 15, 2025
STAR PRIDE
$3,289
$2,399
Tue, Nov 4 - Tue, Nov 18, 2025
WIND SPIRIT
$3,745
$2,499
Sat, Mar 28 - Sun, Apr 12, 2026
WIND SPIRIT
$3,834
$2,499
Tue, Apr 28 - Wed, May 6, 2026
STAR SEEKER
$2,199
$2,199
Wed, Sep 2 - Wed, Sep 16, 2026
STAR SEEKER
$2,799
$2,799