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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
?All-inclusive from
$5,290
?Cruise Only From
$3,599
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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
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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.
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Day 16: Soper's Hole
Arrive at the boardwalk of Pusser’s Landing and mingle with other yachtsmen in the utterly charming marina at Soper’s Hole. Find a deserted stretch of beach to kick back and ponder this tiny port’s rich heritage of romance, pirates, and adventure. An evening departure features a once-in-a-lifetime romantic sunset Sail Away. 
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Day 16: Jost Van Dyke, Great Harbour
For an island comprised of a mere eight square miles, it’s amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis  Drake Waterway. After all that, you’ll be ready for an evening drink on the beach — where you can admire your Windstar ship aglow in the harbor.
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Day 17: Jost Van Dyke, Great Harbour
For an island comprised of a mere eight square miles, it’s amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis  Drake Waterway. After all that, you’ll be ready for an evening drink on the beach — where you can admire your Windstar ship aglow in the harbor.
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Day 18: Virgin Gorda / Prickly Pear, British Virgin Islands
The  beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Althought uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called “The Baths,” which form huge underground pools and caverns
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Day 19: Gustavia
Affectionately known as St. Barts, the Caribbean’s most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island’s signature ti punch as kite surfers fly by.
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Day 20: 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
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
Soper’s Hole
Stroll Pusser’s Landing, the charming boardwalk of Soper’s Hole on your way to a secluded beach
Virgin Gorda
See Virgin Gorda’s lovely beaches like The Baths, Spring Bay and Savannah Bay
Windstar's Signature Beach Party
Indulge yourself at Windstar's Signature Beach Party with plenty of Caribbean flavors and spirit to savor and share
Itinerary at a Glance
Date
Port
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Depart
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Tue Nov 18
Lisbon
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Depart:  7:00 PM
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Wed Nov 19
AT SEA
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Thu Nov 20
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Fri Nov 21
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Sat Nov 22
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Sun Nov 23
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Mon Nov 24
AT SEA
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Tue Nov 25
AT SEA
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Wed Nov 26
AT SEA
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Thu Nov 27
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Fri Nov 28
AT SEA
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Sat Nov 29
AT SEA
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Sun Nov 30
AT SEA
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Mon Dec 1
St. John's
Arrive:  8:00 AM
Depart:  7:00 PM
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Tue Dec 2
Philipsburg, St. Maarten
Arrive:  6:00 AM
Depart:  7:00 PM
Watersports Platform: 
Wed Dec 3
Soper's Hole
Arrive:  10:00 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
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Fri Dec 5
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:  8:00 AM
Depart:  5:00 PM
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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:  
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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 $3,599 per guest
? All-inclusive price from $5,290 per guest
Category BX Deluxe
Category BX Deluxe
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 $3,699 per guest
? All-inclusive price from $5,390 per guest
Category A
Category A
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 $3,899 per guest
? All-inclusive price from $5,590 per guest
Category AX Deluxe
Category AX Deluxe
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 $4,299 per guest
? All-inclusive price from $5,990 per guest
Category TX Deluxe
Category TX Deluxe
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 $4,899 per guest
? All-inclusive price from $6,590 per guest
Suite
Suite
With 376 square feet, you’ll find the perfect space for time together — and plenty of room for time to yourself. You’ll even enjoy two full separate bathrooms. All the amenities of the staterooms await you, plus a beautiful sitting area, and two flat-screen television sets with DVD players.
? Cruise only from $7,499 per guest
? All-inclusive price from $9,190 per guest
Officer's Suite
Officer's Suite
For the ultimate in nautical experiences, reserve the new Officer’s Suite located close to the Bridge where our own ship’s officers have their quarters. With its unique “insider” location and 242 square feet of comfort, the nautically appointed Officer’s Suite offers an experience you won’t find on any other cruise line.
? Call for Availability
Bridge Suite
Bridge Suite
The ultimate in space and style surrounds you in 495 square feet of pure indulgence. Separate bedroom and living room with an in-suite dining area is an invitation to relaxation. And possibly best of all, your expansive bathroom features both a whirlpool spa tub and a massage shower.
? 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
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
Holiday Sailings
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 18 - Sun, Dec 7, 2025
WIND SURF
$5,290
$3,599
THIS
SAILING