Sublime Southern Caribbean
 
Bridgetown to Philipsburg, St. Maarten
Sun Jan 4, 2026 - Wed Jan 14, 2026,
 10 days
 on Wind Spirit
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Bridgetown to Philipsburg, St. Maarten
Spend 10 delightful days exploring Southern Caribbean gems both on and off the beaten path. Hike through Jurassic jungles and breathtaking waterfalls in Dominica. Lounge on white-sand beaches in Antigua. Discover the vintage Caribbean on Guadeloupe’s Les Saintes and tiny Anguilla, and visit French boutiques and restaurants frequented by A-list celebrities on sophisticated St. Barts. When you’re not losing your heart to the enchanting natural beauty or diving into turquoise waters, you’ll find a lost world of colonial history from St. Kitts’ Brimstone Hill fortress and St. John’s Nelson’s Dockyard (both UNESCO sites) to tales of Empress Josephine’s early years on Martinique. You’ll have plenty of time to take in all the sights and activities with four late-evening departures. Plus, your voyage includes access to the Watersports Platform on the stern of your yacht in select ports, where you can paddleboard, kayak, lounge one of our floating mats, or use our water trampoline!
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: 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 3: 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 4: 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 5: 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 6: 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 7: 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 8: 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 9: 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 10: 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 11: 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
Anguilla
In Anguilla, spend the day on Shoal Bay Beach one of the most beautiful beaches in the Caribbean, some say the whole world, with its pinkish hued white sand and intense turquoise water.
Jardin de Balata Botanical Gardens
Take a tour of Anse Mitan’s Jardin de Balata Botanical Gardens with exotic plants from all over the world
Les Saintes
Savor the distinctive French charm of enchanting Les Saintes.
Saint Lucia
Take in the Pitons of Saint Lucia, a UNESCO World Heritage Site renowned for their stunning volcanic peaks, as you sail by.
St. Barts
Get to know the flavor and personality of St. Barts with a late-night stay.
 
Windstar’s Signature Beach Party
Let yourself go at Windstar’s Signature Beach Party, where the Caribbean spirit is in full swing.
Itinerary at a Glance
Date
Port
Arrive
Depart
Watersports
PlatformWatersports Platform: 
Sun Jan 4
Bridgetown
Arrive:  
Depart:  6:00 PM
Watersports Platform: 
Mon Jan 5
Pigeon Island
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Tue Jan 6
Roseau
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Jan 7
Anse Mitan
Arrive:  7:00 AM
Depart:  5:00 PM
Watersports Platform: 
Thu Jan 8
Les Saintes
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Fri Jan 9
Basseterre
Arrive:  9:00 AM
Depart:  9:00 PM
Watersports Platform: 
Sat Jan 10
St. John's
Arrive:  9:00 AM
Depart:  11:00 PM
Watersports Platform: 
Sun Jan 11
Falmouth Harbour
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Jan 12
Gustavia
Arrive:  9:00 AM
Depart:  10:00 PM
Watersports Platform: 
Tue Jan 13
Road Bay
Arrive:  7:00 AM
Depart:  7:00 PM
Watersports Platform: 
Wed Jan 14
Philipsburg, St. Maarten
Arrive:  6:00 AM
Depart:  
Watersports Platform: 
Accommodations & Pricing
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.
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From
Sun, Jan 4 - Wed, Jan 14, 2026
WIND SPIRIT
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