Star Collector: Spectacular Transatlantic Journey: Caribbean to the Azores
 
Philipsburg, St. Maarten to Lisbon
Sat Mar 28, 2026 - Sat Apr 18, 2026,
 21 days
 on Wind Surf
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Starting from $3,999 USD
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Philipsburg, St. Maarten to Lisbon
Relax on the beaches of the Caribbean before you begin your ocean crossing of the Atlantic Ocean towards Portugal. Sample some of the best rum punch in the Caribbean in Road Bay, then head off to the British Virgin Islands, where you can walk along Stroll Pusser’s Landing, the lovely boardwalk of Soper’s Hole on Tortola. Snorkel among the sponges and angelfish in Jost Van Dyke’s Sandy Spit or take a speed boat to Little Bay, Anguilla’s smallest and most private beach to swim. When you dock in Virgin Gorda join an excursion to The Baths, an array of caves with shallow pools created by large boulders. The historic town of Gustavia, the capital city on the island of St. Barthelemy, is where you can explore the 17th-century Fort Gustaf known for its lighthouse and cannons.  Disconnect as you begin the journey across the Atlantic Ocean. Indulge in breakfast in bed while you lounge in your robe all morning before heading to the spa for a massage and a facial; pop into the Open Bridge for an impromptu navigation lesson; make new friends over pre-dinner cocktails as you savor every moment of the exquisite cuisine created by the onboard chefs; and watch the sunset every night before experiencing more stars in the sky than you ever imagined. Wander the charming port of Ponta Delgada, Azores with its medieval fort and look for the art on the jetty, before heading to your final destination– Lisbon.
voyage map
Popular Highlights
Bridge
Drop by the Bridge for an impromptu navigation lesson.
 
Jost Van Dyke
Overnight in Jost Van Dyke for a more in-depth exploration   
 
laundry
Pack light with complimentary daily laundry service.
 
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Sat Mar 28
Philipsburg, St. Maarten
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Sun Mar 29
St. John's
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Mon Mar 30
Road Bay
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Tue Mar 31
Soper's Hole
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Tue Mar 31
Jost Van Dyke, Great Harbour
Arrive:  7:00 PM
Depart:  
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Wed Apr 1
Jost Van Dyke, Great Harbour
Arrive:  
Depart:  10:00 PM
Watersports Platform: 
Thu Apr 2
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Fri Apr 3
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sat Apr 4
Philipsburg, St. Maarten
Arrive:  6:00 AM
Depart:  7:00 PM
Watersports Platform: 
Sun Apr 5
AT SEA
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Mon Apr 6
AT SEA
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Tue Apr 7
AT SEA
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Wed Apr 8
AT SEA
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Thu Apr 9
AT SEA
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Fri Apr 10
AT SEA
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Sat Apr 11
AT SEA
Arrive:  
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Sun Apr 12
AT SEA
Arrive:  
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Mon Apr 13
AT SEA
Arrive:  
Depart:  
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Tue Apr 14
Ponta Delgada
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Apr 15
AT SEA
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Thu Apr 16
AT SEA
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Fri Apr 17
AT SEA
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Sat Apr 18
Lisbon
Arrive:  7:00 AM
Depart:  
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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.
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 $3,999 per guest
? All-inclusive price from $6,078 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
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 28 - Sat, Apr 18, 2026
WIND SURF
$6,078
$3,999
THIS
SAILING