Star Collector: Captivating Caribbean

 
Bridgetown to Oranjestad
Fri Nov 27, 2026 - Sat Dec 12, 2026,
 15 days
 on Star Legend
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Starting from $4,599 USD
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Bridgetown to Oranjestad
Begin in Barbados with a visit to the fairyland magic of Harrison’s Cave before setting sail for the French-Caribbean splendor of Martinique, where Empress Josephine spent her childhood. In St. Lucia enjoy shopping in the bustling capital of Castries, scenic Morne Fortune, and an overnight on Pigeon Island with plenty of beach time and a chance to visit the majestic volcanic Pitons. Follow your nose through the aromatic open-air markets of beautiful St. George’s on the “Isle of Spice.” Enjoy the exclusive Signature Beach Party on Mayreau and walk up Mount Pleasant to witness the amazing view from Fort Hamilton on Bequia. Swim with sea turtles in Tobago Cays Marine Park and listen for the conch beckoning fishing boats home. In Soufriere, feel the heart and soul of St. Lucia when you stroll by street vendors and hike to secluded waterfalls. Bonaire begs you to bring binoculars for bird watching — from flamingos to native parakeets to Amazon parrots. Savor the pastel colors of Old Town Willemstad and explore the limestone formations and ancient petroglyphs of Hato Caves. Complete your voyage in Aruba where you can relax and take in some of the Caribbean’s best beaches or play dominoes with locals.
voyage map
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Day 1: Bridgetown
Jolly old England comes to life in the city and its garrison, both UNESCO World Heritage Sites. Further afield, you’ll find historic sugar plantations and the fairyland magic of Harrison’s Cave.
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Day 2: Anse Mitan
Martinique offers a delightful and distinctive blend of French and Caribbean influences, with a bounty of historical sites, museums and a wide array of excellent shopping. Be sure to take a tour of the beautiful Jardin de Balata Botanical Gardens with exotic plants from around the world and a treetop walkway affording mountain views.
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Day 3: Pigeon Island
The UNESCO site Pitons’ with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.
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Day 4: Pigeon Island
The UNESCO site Pitons’ with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.
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Day 4: Castries
The capital and largest city of St. Lucia is a bustling port where shoppers flock.  Most of the city’s historic buildings were destroyed in major fires between 1785 and 1948 but you’ll see the beautiful, scenic backdrop of Morne Fortune (elev. 2,795 ft.) and the bustling harbor.  Visit the Castries Market for handicrafts, fruits and vegetables, see the murals painted by a local artist and housed in the Cathedral of the Immaculate Conception, and check out one of the many restaurants or Derek Walcott Square.
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Day 4: The Pitons
Located near the town of Soufriere, St. Lucia the Pitons are a UNESCO World Heritage Site and a spectacular landmark. Gros Piton is 2,619 feet high (798 meters) and Petit Piton is 2,438 feet high (743 meters). Gros Piton is home to at least 148 plant species and 27 bird species (5 of them endemic) and Petit Piton has 97 plant species with 8 rare tree species.
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Day 5: Mayreau
With fewer than 300 inhabitants and miles of secluded beaches, it's easy to feel as if you're on your own private island. Saline Bay is a delightful anchorage that separates the Caribbean from the Atlantic - and a perfect place to play with some of the toys from the Watersports Platform.
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Day 6: St. George's
Inhale the intoxicating aroma of the “Isle of Spice” as your eyes feast on what is widely claimed to be the most beautiful city in the Caribbean. Spend the day on 2-mile-long Grand Anse beach, and before you go, a taste of nutmeg ice cream is a must.
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Day 7: Bequia
The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequia’s whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the island’s famed model boat builders at work on their miniature masterpieces.
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Day 8: Bridgetown
Jolly old England comes to life in the city and its garrison, both UNESCO World Heritage Sites. Further afield, you’ll find historic sugar plantations and the fairyland magic of Harrison’s Cave.
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Day 9: Rodney Bay
Rodney Bay, Saint Lucia
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Day 9: The Pitons
Located near the town of Soufriere, St. Lucia the Pitons are a UNESCO World Heritage Site and a spectacular landmark. Gros Piton is 2,619 feet high (798 meters) and Petit Piton is 2,438 feet high (743 meters). Gros Piton is home to at least 148 plant species and 27 bird species (5 of them endemic) and Petit Piton has 97 plant species with 8 rare tree species.
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Day 10: Scarborough, Tobago
Scarborough, Tobago
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Day 11: Bequia
The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequia’s whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the island’s famed model boat builders at work on their miniature masterpieces.
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Day 12: Mayreau
With fewer than 300 inhabitants and miles of secluded beaches, it's easy to feel as if you're on your own private island. Saline Bay is a delightful anchorage that separates the Caribbean from the Atlantic - and a perfect place to play with some of the toys from the Watersports Platform.
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Day 14: Kralendijk
The ice cream colors of the stucco houses will draw your lens, as will the pink flamingos on the salt pans. But you’ll need a waterproof camera to complete the portrait since more than 400 fish species and 50 types of coral wait beneath the surface
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Day 15: Willemstad
Savor the pastel colors of the historic UNESCO site Old Town and the way the elaborate Dutch gables cut baroque curlicues from the sky. It’s the perfect appetizer for a day of watersports or an adventure below ground at the magical Hato Caves—filled with eerie limestone formations and ancient petroglyphs.
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Day 16: Oranjestad
Known for having some of the best beaches in the Caribbean, this Dutch port makes it easy to just … take it easy. Walk through town to choose your favorite carved wooden door, or spend the day like the Arubans do playing dominos at a beachside table.
Popular Highlights
Anse Mitan
In Anse Mitan find the Anse Cafard Slave Memorial commemorating the lives of 20 slaves who were not provided a proper burial
 
Beach Party
Enjoy the exclusive Signature Beach Party on Mayreau
 
Bonaire
Bring out your binoculars for Bonaire birdwatching as you look for flamingos, native parakeets and Amazon parrots
 
Complimentary laundry
Pack light with complimentary daily laundry service
 
St. Lucia
Overnight at Pigeon Island with more time beachside at the national park there
 
Tobago
Swim with sea turtles in Tobago Cays Marine Park
 
Willemstad
Savor the pastel colors of Willemstad’s Old Town, a UNESCO site
 
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Fri Nov 27
Bridgetown
Arrive:  
Depart:  6:00 PM
Watersports Platform: 
Sat Nov 28
Anse Mitan
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Sun Nov 29
Pigeon Island
Arrive:  8:00 AM
Depart:  
Watersports Platform: 
Mon Nov 30
Pigeon Island
Arrive:  
Depart:  6:00 AM
Watersports Platform: 
Mon Nov 30
Castries
Arrive:  8:00 AM
Depart:  3:00 PM
Watersports Platform: 
Mon Nov 30
The Pitons
Arrive:  5:30 PM
Depart:  6:30 PM
Watersports Platform: 
Tue Dec 1
Mayreau
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Dec 2
St. George's
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Thu Dec 3
Bequia
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Fri Dec 4
Bridgetown
Arrive:  5:00 AM
Depart:  6:00 PM
Watersports Platform: 
Sat Dec 5
Rodney Bay
Arrive:  3:00 PM
Depart:  8:00 AM
Watersports Platform: 
Sat Dec 5
The Pitons
Arrive:  5:30 PM
Depart:  6:30 PM
Watersports Platform: 
Sun Dec 6
Scarborough, Tobago
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Mon Dec 7
Bequia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Tue Dec 8
Mayreau
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Dec 9
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Thu Dec 10
Kralendijk
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Fri Dec 11
Willemstad
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Sat Dec 12
Oranjestad
Arrive:  6:00 AM
Depart:  
Watersports Platform: 
Accommodations & Pricing
Guaranteed Suite** (chosen by Windstar)
Guaranteed Suite** (chosen by Windstar)
Guaranteed Suite** (chosen by Windstar)
? Call for Availability
Star Porthole Suite
Star Porthole Suite
These rooms represent a nod to the sailing tradition of porthole windows. And while sailors might have had cramped quarters, your 277 square foot stateroom is wonderfully spacious and furnished with all the modern amenities and comforts of home.
? Cruise only from $4,599 per guest
? All-inclusive price from $4,599 per guest
Ocean View Suite
Ocean View Suite
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, and savor a treat from the fresh fruit bowl.
? Cruise only from $4,749 per guest
? All-inclusive price from $4,749 per guest
Ocean View Suite 1
Ocean View Suite 1
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $4,899 per guest
? All-inclusive price from $4,899 per guest
Star Ocean View Suite 1
Star Ocean View Suite 1
As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.
? Cruise only from $5,219 per guest
? All-inclusive price from $5,219 per guest
Ocean View Suite 2
Ocean View Suite 2
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $5,379 per guest
? All-inclusive price from $5,379 per guest
Ocean View Suite 3
Ocean View Suite 3
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $5,699 per guest
? All-inclusive price from $5,699 per guest
Balcony Suite
Balcony Suite
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $7,019 per guest
? All-inclusive price from $7,019 per guest
Star Balcony Suite
Star Balcony Suite
As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.
? Cruise only from $7,099 per guest
? All-inclusive price from $7,099 per guest
Balcony Suite 1
Balcony Suite 1
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $7,499 per guest
? All-inclusive price from $7,499 per guest
Star Balcony Suite 1
Star Balcony Suite 1
As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.
? Cruise only from $7,699 per guest
? All-inclusive price from $7,699 per guest
Deluxe Suite
Deluxe Suite
Brand new Deluxe Suites welcome you with 468 square feet of casually elegant living space and an ocean viewing French balcony. All these suites feature 3rd berths, and a sleep-inducing queen bed.
? Cruise only from $9,499 per guest
? All-inclusive price from $9,499 per guest
Classic Suite
Classic Suite
Relax in 400 spacious square feet. Your living area offers beautiful views from the forward-facing window and French doors onto your private veranda. Two spacious closets give you plenty of room to unpack.
? Cruise only from $11,299 per guest
? All-inclusive price from $11,299 per guest
Owner's Suite
Owner's Suite
With 575 square feet, your Owner’s Suite offers separate living room and dining areas. A veranda, Interactive TVs, and a full master bath and separate powder room indulge you in spacious comfort. 
? Cruise only from $13,499 per guest
? All-inclusive price from $13,499 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
Marina
*Select voyages
Enjoy regionally inspired treatments at World Spa by Windstar
Relax With A Morning Yoga Session
ALL DATES &
FARES
Thankful For Travel Sales Event
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
Sun, Jan 18 - Sun, Feb 1, 2026
WIND SURF
Call For Availability
Fri, Nov 27 - Sat, Dec 12, 2026
STAR LEGEND
$4,599
$4,599
THIS
SAILING