Star Collector: The Best of the Windward & Leeward Isles
 
28 DAYS
Star Pride
St. Maarten to Oranjestad
Departure Date:
?Cruise only from $8,599 USD per guest
? All-inclusive from $11,091 USD per guest
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St. Maarten to Oranjestad
Explore the Caribbean’s most picturesque destinations and little-known treasures while indulging in a longer cruise vacation along the most scenic stops throughout the Windward and Leeward Islands and relaxing afternoon in the warm Caribbean off the Watersports Platform. Swim amid sea turtles, colorful coral, eagle rays, and parrot fish during a snorkel safari off the coast of St. Kitts. Buzz about with a beekeeping guide and sample the delicious sweetness of rare and exotic Black Mangrove honey during an agricultural collective tour outside of Castries. Kayak to a beachside village for beverages and souvenirs during an overnight stay in Jost Van Dyke. Dine on conch fritters paired with tropical refreshments. Walk in the childhood footsteps of the future Empress Josephine among flowers and rustic gardens at the Pagerie Habitation, a former sugar plantation on Martinique. Seek out brown pelicans, blue herons, and iconic pink flamingos while gliding silently along lattice-like mangrove roots in Lac Bay National Park on Bonaire.
voyage map
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Day 1: 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: Falmouth Harbour
It’s said that Antigua has 365 beaches – one for every day of the year. See how many you can discover as our stay in port stretches into the evening to accommodate them all. Watch the stars come out as darkness falls and imagine how residents of Andromeda must envy you.
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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 sunset Sail Away and cruise that glides along Sir Francis Drake Channel and on through “The Narrows.”
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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
A beautiful coral reef wavers just beneath you as your ship makes the break into the heart of Spanish Town, the Yacht Harbor Marina,Located to the south of Spanish Town lies the curious assembly of house-sized boulders called “The Baths,” which form huge underground pools and caverns that you’re free to explore.
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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: 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 9: Basseterre
With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean’s small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.
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Day 10: 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 11: Little Bay
Today we visit “Pompeii of the Caribbean”—an island that is half lush and green, half gray and covered in ash by a volcano in 1995. And if a half-buried city isn’t intriguing enough, there are black-sand beaches and a perplexing Irish heritage to explore.
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Day 12: Les Saintes
This is the Caribbean as you’ve always imagined it, with yacht-filled harbors set against volcanic mountains and endless stretches of palm-fringed beach. The underwater world here attracted the likes of Jacques Cousteau, but even novice snorkelers will enjoy exploring these impossibly blue waters.
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Day 13: Roseau
Get ready for a full day with plenty to do. Snorkel alongside brilliant parrot fish in the bubbly waters of Champagne Beach. Take a break to enjoy more than 150 species of plants and brilliant red-necked Jaco parrots at the botanical gardens. If you’re up for an optional hike, don’t miss Boiling Lake and the Valley of Desolation at Dominica’s Morne Trois Pitons National Park, a UNESCO World Heritage Site.
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Day 14: 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 15: 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 16: 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 17: 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 17: 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 17: 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 18: 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 19: 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 20: 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 21: 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 22: 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 23: Man-O-War Bay
Listen for the sound of a conch announcing the return of the fishing boats. Bobbing next to us are flotillas of pelicans – hinting at the excellent snorkeling waiting for you here and in neighboring Pirate’s Bay.
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Day 24: 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 25: Soufriere
Nestled in the shadows of the UNESCO Pitons, Soufriere represents the heart and soul of St. Lucia. The tiny town center is full of street vendors and stores and some of the best resorts on the island can be found here. Nearby are secluded waterfalls and the waters here boast some of the best diving around. Sights to see include the Edmund Rainforest Trail, fond Doux Holiday plantation, Robot Estate and the Gros Piton Nature Trail.
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Day 27: 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 28: 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 29: 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
Gustavia Late Night Stays
Late night stays in Gustavia, Pigeon Island, and Les Saintes let you really experience the flavor of these distinct places
Jost Van Dyke
Relish extra beach time with an overnight in Jost Van Dyke
Roseau
Wander the compact, noisy streets of Roseau’s French Quarter
St. Lucia
During your sunset cruise, take a picture of the Piton's two volcanic peaks, a UNESCO site rising more than 2,400 feet on St. Lucia
Tobago
Snorkel the impressive coral reefs of Tobago’s Man-O-War Bay at the confluence of the Atlantic and Caribbean Sea
Willemstad
Known for its brightly colored architecture, Willemstad is a UNESCO site
Complimentary laundry
Pack light with complimentary daily laundry service
 
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.
Cooking Demonstrations
Open Bridge
Friendly and Relaxed Atmosphere
Local and Live Performances
Signature Sail Away
Crew Talent Show
Enjoy regionally inspired treatments at World Spa by Windstar
Take In The Sun
Complimentary 24 Hour Room Service
Relax at the Pool or Hot Tub
Relax With A Morning Yoga Session
Genuine and Thoughtful Crew
Signature Onboard Barbecue
Shopping With The Chef
Watersports Platform
Accommodations & Pricing
This all-suite ship completed renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love.
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 $8,599 per guest
? All-inclusive price from $11,091 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, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $8,899 per guest
? All-inclusive price from $11,391 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 $10,099 per guest
? All-inclusive price from $12,591 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 $10,899 per guest
? All-inclusive price from $13,391 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 $12,399 per guest
? All-inclusive price from $14,891 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 $12,799 per guest
? All-inclusive price from $15,291 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 $13,599 per guest
? All-inclusive price from $16,091 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 $13,999 per guest
? All-inclusive price from $16,491 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 easily converted to twins.
? Cruise only from $16,099 per guest
? All-inclusive price from $18,591 per guest
Classic Suite
Classic Suite
Relax in 400 to 530 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 $19,099 per guest
? All-inclusive price from $21,591 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, two flat-screen TVs and DVD players, and a full master bath and separate powder room indulge you in spacious comfort. 
? Cruise only from $23,299 per guest
? All-inclusive price from $25,791 per guest
Guaranteed Suite** (chosen by Windstar)
Guaranteed Suite** (chosen by Windstar)
Guaranteed Suite** (chosen by Windstar)
? Call for Availability
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.
? Call for Availability
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.
? Call for Availability
Guaranteed Balcony Suite** (chosen by Windstar)
Guaranteed Balcony Suite** (chosen by Windstar)
Guaranteed Balcony Suite** (chosen by Windstar)
? Call for Availability
Star Pride
Carrying only 312 guests, Star Pride still tucks into small ports like Le Lavandou and Wrangell or narrow waterways like the Corinth and Keil Canal. We can’t wait to welcome you onboard for your next 180 degree from ordinary adventure! Learn more about the newly renovated ship and the $250 Million Star Plus Initiative.
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! ITINERARY CHANGE St. Maarten TO Oranjestad 28 days on Star Pride X
Please note that this itinerary has been updated
Date
Port
Arrive
Depart
Sat Nov 4
St. Maarten
Arrive:
Depart:7:00 PM
Sun Nov 5
Falmouth Harbour
Arrive:8:00 AM
Depart:6:00 PM
Mon Nov 6
Road Bay
Arrive:8:00 AM
Depart:6:00 PM
Tue Nov 7
Soper's Hole
Arrive:8:00 AM
Depart:6:00 PM
Tue Nov 7
Jost Van Dyke, Great Harbour
Arrive:7:00 PM
Depart:
Wed Nov 8
Jost Van Dyke, Great Harbour
Arrive:
Depart:10:00 PM
Thu Nov 9
Virgin Gorda
Arrive:8:00 AM
Depart:5:00 PM
Fri Nov 10
Gustavia
Arrive:8:00 AM
Depart:10:00 PM
Sat Nov 11
St. Maarten
Arrive:6:00 AM
Depart:7:00 PM
Sun Nov 12
Basseterre
Arrive:8:00 AM
Depart:9:00 PM
Mon Nov 13
Gustavia
Arrive:8:00 AM
Depart:10:00 PM
Tue Nov 14
Little Bay
Arrive:8:00 AM
Depart:10:00 PM
Wed Nov 15
Les Saintes
Arrive:8:00 AM
Depart:5:00 PM
Thu Nov 16
Roseau
Arrive:8:00 AM
Depart:5:00 PM
Fri Nov 17
Pigeon Island
Arrive:7:00 AM
Depart:4:00 PM
Sat Nov 18
Bridgetown
Arrive:5:00 AM
Depart:6:00 PM
Sun Nov 19
Pigeon Island
Arrive:8:00 AM
Depart:
Mon Nov 20
Pigeon Island
Arrive:
Depart:6:00 AM
Mon Nov 20
Castries
Arrive:8:00 AM
Depart:3:00 PM
Mon Nov 20
The Pitons
Arrive:5:30 PM
Depart:6:30 PM
Tue Nov 21
Anse Mitan
Arrive:8:00 AM
Depart:6:00 PM
Wed Nov 22
Mayreau
Arrive:8:00 AM
Depart:6:00 PM
Thu Nov 23
St. George's
Arrive:8:00 AM
Depart:10:00 PM
Fri Nov 24
Bequia
Arrive:8:00 AM
Depart:5:00 PM
Sat Nov 25
Bridgetown
Arrive:5:00 AM
Depart:6:00 PM
Sun Nov 26
Man-O-War Bay
Arrive:8:00 AM
Depart:5:00 PM
Mon Nov 27
Mayreau
Arrive:8:00 AM
Depart:6:00 PM
Tue Nov 28
Soufriere
Arrive:8:00 AM
Depart:4:00 PM
Wed Nov 29
AT SEA
Arrive:
Depart:
Thu Nov 30
Willemstad
Arrive:8:00 AM
Depart:10:00 PM
Fri Dec 1
Kralendijk
Arrive:8:00 AM
Depart:6:00 PM
Sat Dec 2
Oranjestad
Arrive:6:00 AM
Depart: