Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossing
 
Lisbon to Philipsburg, St. Maarten
Tue Nov 18, 2025 - Sun Dec 7, 2025,
 19 days
 on Wind Surf
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Starting from $3,599 USD
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Lisbon to Philipsburg, St. Maarten
Caribbean beaches, vibrant tropical fish, and savory West Indies cuisine during this 19-day transatlantic crossing. Relax, unwind and refocus with back-to-back spa days throughout your ocean crossing and dine on award-winning meals paired with the company of your new Windstar family. Relive history while sailing aboard a former America's Cup competition sailboat or cook up delicious French meals with a certified chef in Grand Case outside Philipsburg, St. Maarten. Roll out in offroad vehicles for an unrushed day of snorkeling and relaxing on Tortola's secluded beaches. Swim and frolic with dolphins near Jost Van Dyke in the British Virgin Islands. Snorkel above colorful coral and dizzying schools of curious fish prior to your private beach barbeque on Virgin Gorda in the British Virgin Islands. Glide over a sunken ship in a semi-submersible and take in a glowing Caribbean sunset during a catamaran cruise off Gustavia's tropical beaches on St. Barts.
voyage map
Popular Highlights
Complimentary laundry
Pack light with complimentary daily laundry service
 
Crossing
Find time for your favorite indulgences – from a relaxing massage to breakfast in your room during your days crossing the Atlantic
Gustavia
A late night stay in Gustavia lets you really get time to get the flavor of this distinct place
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
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Thu Nov 20
AT SEA
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Fri Nov 21
AT SEA
Arrive:  
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Sat Nov 22
AT SEA
Arrive:  
Depart:  
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Sun Nov 23
AT SEA
Arrive:  
Depart:  
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Mon Nov 24
AT SEA
Arrive:  
Depart:  
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Tue Nov 25
AT SEA
Arrive:  
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Wed Nov 26
AT SEA
Arrive:  
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Thu Nov 27
AT SEA
Arrive:  
Depart:  
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Fri Nov 28
AT SEA
Arrive:  
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Sat Nov 29
AT SEA
Arrive:  
Depart:  
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Sun Nov 30
AT SEA
Arrive:  
Depart:  
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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:  7:00 PM
Watersports Platform: 
Wed Dec 3
Soper's Hole
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Dec 3
Jost Van Dyke, Great Harbour
Arrive:  7:00 PM
Depart:  
Watersports Platform: 
Thu Dec 4
Jost Van Dyke, Great Harbour
Arrive:  
Depart:  10:00 PM
Watersports Platform: 
Fri Dec 5
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sat Dec 6
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sun Dec 7
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
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
Tue, Nov 18 - Sun, Dec 7, 2025
WIND SURF
$5,480
$3,599
THIS
SAILING