Knot Your Average Crossing
 
Lisbon to Philipsburg, St. Maarten
Tue Nov 18, 2025 - Tue Dec 2, 2025,
 14 days
 on Wind Surf
VIEW ALL DATES
Starting from $2,899 USD
ADD TO
WISH LIST
REMOVE
FROM
WISH LIST
VIEW THE JOURNEY
Lisbon to Philipsburg, St. Maarten
Set sail on an unforgettable ocean crossing aboard one of our majestic sailing ships, where you’ll immerse yourself in the timeless art of seafaring. This voyage features a guest speaker offering fascinating talks on navigation history, legendary explorers, and even swashbuckling pirates. You’ll learn to read charts, tie sailor’s knots, and even navigate the vessel on the Flying Bridge alongside our Officers. Enjoy stargazing and star mapping sessions, and hear navigational insights directly from the Captain himself. Throughout the journey, hands-on workshops and immersive activities will deepen your connection to the sea — and for a final splash of fun, join our lively "Pirates of the Atlantic” themed party, so don’t forget to pack your nautical outfits!
voyage map
Popular Highlights
Bridge
Learn how to navigate the vessel on the Flying Bridge.
cuisine
Indulge in gourmet dining options with dishes created by James Beard Foundation award winning chefs.
Private Yacht Lifestyle
Private yacht lifestyle with no interruptions.
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Tue Nov 18
Lisbon
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Wed Nov 19
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Thu Nov 20
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Nov 21
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sat Nov 22
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sun Nov 23
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Mon Nov 24
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Tue Nov 25
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Wed Nov 26
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Thu Nov 27
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Nov 28
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sat Nov 29
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sun Nov 30
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Mon Dec 1
St. John's
Arrive:  8:00 AM
Depart:  7:00 PM
Watersports Platform: 
Tue Dec 2
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
Christmas in July Sales Event
Go All-Inclusive — On Us
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
Tue, Nov 18 - Tue, Dec 2, 2025
WIND SURF
$2,899
$2,899
THIS
SAILING
Sat, Mar 28 - Sun, Apr 12, 2026
WIND SPIRIT
$2,899
$2,899
Sat, Apr 4 - Sat, Apr 18, 2026
WIND SURF
$3,985
$2,599
Tue, Nov 10 - Tue, Nov 24, 2026
WIND STAR
$3,885
$2,499