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
?All-inclusive from
$5,868
?Cruise Only From
$3,999
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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
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Day 1: 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 2: 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 3: Road Bay
With its protected shoreline, calm surf, spectacular coral reefs and sugar-soft beaches, Road Bay has become a destination for boaters, with its delightful restaurants, bars, and shops. Anguilla has some of the most beautiful sunsets and delicious rum punch to be found in the Caribbean.  It is also home to Cuban tree frogs, red-footed tortoise, green iguanas and five species of bats.  Worth checking out is Wallblake House, a heritage plantation house and museum said to be the oldest building on the island and located nearby.
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Day 4: 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 4: 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 5: 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 6: 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 7: 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 8: 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 18: Ponta Delgada
Ponta Delgada is the capital of São Miguel Island, gateway to the crater lakes and volcano of Sete Cidades and to the Azores Archipelago of Portugal. There is much to do here including horseback riding, golfing, and inviting beaches with volcanic sand, tidal pools and inviting surfing or body boarding.  Sites to see include the impressive, 3-arched city gates and the Gothic-style Church of St. Sebastian near the harbor, the Hermitage of Our Lady of Peace Temple, the quirky street art and the Carlos Machado Museum with a variety of artifacts of  the Azorean culture.
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Day 22: 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.
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.
 
Ponta Delgada
Stretch your legs and wander the charming Azores port of Ponta Delgada.
 
Pusser’s Landin
Stroll Pusser’s Landing, the charming boardwalk of Soper’s Hole on your way to a secluded beach   
 
Signature Beach Party
Enjoy Windstar’s exclusive Signature Beach Party at Prickly Pear Beach   
 
spa
Find you have time for your favorite indulgences – from a relaxing visit to the spa to breakfast in bed.
Virgin Gorda
Soak in the natural bathing pools of "The Baths" at Virgin Gorda.
Itinerary at a Glance
Date
Port
Arrive
Depart
Watersports
PlatformWatersports Platform: 
Sat Mar 28
Philipsburg, St. Maarten
Arrive:  
Depart:  7:00 PM
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Sun Mar 29
St. John's
Arrive:  8:00 AM
Depart:  5:00 PM
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Mon Mar 30
Road Bay
Arrive:  8:00 AM
Depart:  6:00 PM
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Tue Mar 31
Soper's Hole
Arrive:  8:00 AM
Depart:  6:00 PM
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Tue Mar 31
Jost Van Dyke, Great Harbour
Arrive:  7:00 PM
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Wed Apr 1
Jost Van Dyke, Great Harbour
Arrive:  
Depart:  10:00 PM
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Thu Apr 2
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:  8:00 AM
Depart:  5:00 PM
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Fri Apr 3
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
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Sat Apr 4
Philipsburg, St. Maarten
Arrive:  6:00 AM
Depart:  7:00 PM
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Sun Apr 5
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Mon Apr 6
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Tue Apr 7
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Wed Apr 8
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Thu Apr 9
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Fri Apr 10
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Sat Apr 11
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Sun Apr 12
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Mon Apr 13
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Tue Apr 14
Ponta Delgada
Arrive:  8:00 AM
Depart:  6:00 PM
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Wed Apr 15
AT SEA
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Thu Apr 16
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Fri Apr 17
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Sat Apr 18
Lisbon
Arrive:  7:00 AM
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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 $5,868 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 $4,249 per guest
? All-inclusive price from $6,118 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 $4,399 per guest
? All-inclusive price from $6,268 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 $4,799 per guest
? All-inclusive price from $6,668 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 $5,399 per guest
? All-inclusive price from $7,268 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 $8,499 per guest
? All-inclusive price from $10,368 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.
? Cruise only from $8,899 per guest
? All-inclusive price from $10,768 per guest
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.
? Cruise only from $11,599 per guest
? All-inclusive price from $13,468 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
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
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
Sat, Mar 28 - Sat, Apr 18, 2026
WIND SURF
$5,868
$3,999
THIS
SAILING