Windstar Cruises Caribbean: 10 nights from Bridgetown with Wind Spirit
Jan 4, 2026
Barbados, Saint Vincent and the Grenadines, Dominica, Martinique, France, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy, British Virgin Islands, Sint Maarten
Cruise itinerary
Departure Port: Bridgetown ➞
Landing: Philipsburg
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Sunday, January 4, 2026 - 6:00 PMBridgetown
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Monday, January 5, 2026 8:00 AM - 5:00 PMMayreau
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Tuesday, January 6, 2026 1:00 PM - 6:00 PMRoseau
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Wednesday, January 7, 2026 7:00 AM - 5:00 PMFort de france
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Thursday, January 8, 2026 8:00 AM - 5:00 PMDeshaies
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Friday, January 9, 2026 8:00 AM - 9:00 PMBasseterre
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Saturday, January 10, 2026 9:00 AM - 11:00 PMSaint Johns
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Sunday, January 11, 2026Navigation
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Monday, January 12, 2026 9:00 AM - 10:00 PMGustavia
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Tuesday, January 13, 2026 7:00 AM - 7:00 PMTortola Island
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Wednesday, January 14, 2026 6:00 AM 11:59 PMPhilipsburg

Bridgetown
Bridgetown, an island located in the eastern part of the archipelago, is the capital of Barbodos islands. It is renowned for its duty-free shops and its cultural and historical attractions.
It is one of the most oldiest cities of the Carribean Islands; its architecture full of colonial buildings blending with warehouses and brash modern office blocks fascinates and entertains visitors. The center of the city is the Carenaggio, a tourist port that confines with the Parliament of Barbados (where are located two small fashinated history museums). Some of the most famous religious buildings are distant five minutes from the Parliament like Sant Micheal Cathedral and the synagogue.
Bridgetown is one of the oldest cities in the Caribbean; its architecture with balconies of colonial buildings blending with warehouses and brash modern office blocks fascinates and entertains visitors. The center of activity is the careenage, a marina that borders the Barbados Parliament (home to two small but fascinating local history museums). A number of the island's most important religious buildings are located within a five-minute walk of Parliament, including St. Michael's Cathedral and a synagogue.

Mayreau

Roseau

Fort de france
Cruises departing from Fort de France: all offersFort de France, the capital of the island of Martinique, is the ideal embarkation port for those who wish to visit the Antilles on a cruise. From this port, cruise ships depart with stops in the main islands of this region: Barbados, Grenada, Montserrat and Dominica are just some of the fantastic islands you will visit by booking a cruise from Fort de France!
Cruise from Fort de France: the best of the CaribbeanThe city of Fort de France has a typically French atmosphere with many clubs, bars and restaurants located in the center or on the waterfront. From the port of Fort de France you can easily reach the most exotic islands of the Lesser and Greater Antilles: dive among the sun, palm trees and crystal clear waters during the stops and enjoy all the comfort of your cabin on board during the navigation moments.
For those who decide to visit Fort de France, we recommend a visit to the botanical garden or the municipal park 'La Savane' where you can admire exotic plants, flowers and trees of incredible colors and scents. For lovers of good food, we recommend a stop in one of the many typical restaurants that combine refined French cuisine with the exotic flavors of the Caribbean: a unique mix not to be missed!
The best time for a cruise from Fort de France is from November to April, the freshest and driest months in this region. The cruises from Fort de France are ideal for sea lovers who can sunbathe or snorkel among colorful tropical fish.
Families with children are also welcome in Fort de France: they will find beaches to play on and many activities to do together in this lovely city before setting sail for the cruise. Browse below for cruises from Fort de France, find the right itinerary for you at the best price and book an unforgettable cruise for a winter vacation in the name of sun and sea!

Deshaies
Located on the north-west coast, a small fishing village surrounded by high wooded hills, Deshaies is full of charm. Charming small fishing village surrounded by green hills, Deshaies is probably one of the most peaceful places in Guadeloupe. It is in the less populated region of the island that will make you discover the charm of a traditional village with huts and wooden houses in Caribbean style, restaurants, shops and above all, the largest beaches in the entire archipelago. Today, Deshaies is aimed at a solidarity tourism, ecotourism actively involved in the development of the city. Small town with high tourist potential to the north west of Basse-Terre, this territory where sea, mountains, rivers, beaches and valleys form an extraordinary landscape. A road along the Caribbean Sea offers a splendid view of the coast, especially at sunset. Far from the hustle and bustle of the crowds, you can enjoy the landscape of this exceptional site. Wooden houses, colonial style houses, cottages or even eco-lodges are the charm of the city. In fact, the population does not lack friendly addresses. Take the time to savor Caribbean flavors in one of the ten restaurants in the city, you won't be disappointed! 2 km from Deshaies, is the most beautiful beach in Basse-Terre, the famous Grande Anse beach, known for its red sand and many coconut trees. The city, which extends over just under 5,000 inhabitants, has preserved, despite its tourist attractions, a real authenticity. In addition to its beautiful beaches, Deshaies also has beautiful gardens and parks. If you love flowers, tropical plants, animals, all in a serene and relaxing atmosphere, visit the botanical garden of the country, one of the main attractions in Guadeloupe.
Basseterre
During your stop in Basseterre, the lively capital of Saint Kitts and Nevis, get ready to immerse yourself in an authentic Caribbean experience. Start with a walk in the heart of the city, exploring the bustling Independence Square, surrounded by historic colonial-style buildings and colorful local markets. Visit the Immaculate Conception Cathedral and the historic Brimstone Hill Fortress, a UNESCO World Heritage site.
Walk through the imposing walls of the fortress and enjoy breathtaking panoramic views of the ocean and the surrounding islands. For closer contact with nature, head to the Romney Manor Botanical Gardens, where you can admire a vast array of tropical flora.
If you are looking for relaxation, relax on the pristine beaches of South Friars Bay or Cockleshell Beach. The turquoise waters and white sand create a perfect environment for swimming, snorkeling or simply enjoying the sun. Basseterre awaits you with its natural and cultural wonders.
Basseterre: A Caribbean Gem for Your Cruise DepartureEmbark on an idyllic Caribbean adventure from Basseterre, the charming capital of St. Kitts. This vibrant port city, with its colonial architecture and lively atmosphere, offers a captivating starting point for your tropical escape. Explore historical sites like Brimstone Hill Fortress, wander through colorful markets, and soak in the island's lush beauty before setting sail. Basseterre promises a warm welcome and a taste of authentic Caribbean life before you even step aboard your luxurious cruise ship.
Tropical Horizons Await from BasseterreCruises departing from Basseterre lead to some of the most breathtaking destinations in the Lesser Antilles and beyond. Imagine waking up to new islands each day, from the pristine beaches of Antigua to the volcanic landscapes of St. Lucia. Whether you seek thrilling water sports, serene relaxation, or vibrant local culture, your journey from Basseterre will be filled with unforgettable moments. The convenience and beauty of this port make it an ideal choice for those dreaming of a truly immersive Caribbean cruise experience, leaving you refreshed and inspired by every stop.

Saint Johns
Its ideal climate, the incredible landscape, a pleasant lifestyle and a beach for every day of the year make Saint John's a dream vacation destination.
Fascinating History of Saint Johns in Antigua and BarbudaSaint Johns, located in Antigua and Barbuda, has a captivating history that dates back to the colonial era. Founded by the British in the 17th century, the city played a significant role as a strategic port in the Caribbean Sea. Over the centuries, Saint Johns has evolved into a vibrant cultural and tourist hub, preserving traces of its colonial past in its architecture and traditions.
Tropical Climate and Sunny DaysSaint Johns enjoys a tropical climate with warm temperatures and plenty of sunshine throughout the year. Summers are hot and humid, perfect for lounging on the white sandy beaches and swimming in the crystal-clear waters of the island. Winters are mild and dry, providing optimal conditions for exploring the city and its attractions without being hindered by rainfall.
Top Attractions and Places to Explore in Saint JohnsSaint Johns offers a plethora of attractions that cater to all interests. The historic Nelson's Dockyard, a UNESCO World Heritage Site, showcases naval history and stunning views of English Harbour. The colorful markets of Redcliffe Quay are ideal for shopping for local crafts and souvenirs. Don't miss out on visiting Shirley Heights for panoramic vistas and lively sunset parties.
Local Cuisine: Authentic Flavors of Antigua and BarbudaThe culinary scene in Saint Johns reflects the rich gastronomic heritage of Antigua and Barbuda with dishes that tantalize the taste buds. Indulge in seafood delights like grilled lobster, spicy pepperpot stew, and sweet potato pudding. Sample local delicacies such as saltfish with fungee (cornmeal dish) and savor rum punch or Wadadli beer for a true taste of the islands.
Embark on an Unforgettable Cruise from Saint JohnsTo enhance your visit to Saint Johns in Antigua and Barbuda, consider booking a cruise departing from this picturesque city. Cruises around the surrounding islands offer breathtaking views of the turquoise Caribbean waters, pristine beaches, and vibrant coral reefs. Booking a cruise from Saint Johns guarantees unforgettable experiences and a deeper connection to the natural beauty of the Caribbean islands.

Gustavia
Gustavia is the capital of Saint Barthélemy, a Caribbean island that combines French charm with tropical warmth. During a cruise ship stop, there are many exciting activities to do and places to explore.
Start your visit with a walk through the center of Gustavia, where you can admire the colorful colonial-style houses, shop in luxury boutiques and enjoy local cuisine in fine restaurants and cafes. The port of Gustavia is also an ideal place for a relaxing walk, with breathtaking views of the boats and yachts moored there.
The island's history is well represented by Fort Gustav, which offers a panoramic view of the city and the harbor. The fort is a great place to take photos and learn about the colonial history of Saint Barthélemy.
For sea lovers, there are several nearby beaches that are worth visiting. Shell Beach, a short walk from the center, is perfect for swimming and relaxing. If you prefer a more adventurous experience, you can go snorkeling or scuba diving in the crystal clear waters around the island, exploring the rich marine life and coral reefs.
A visit to the many art galleries and museums in Gustavia cannot be missed, where you can discover local art and culture. Finally, end your day with a romantic dinner in one of the restaurants overlooking the sea, savoring French and Caribbean cuisine while the sun sets on the horizon.
In summary, Gustavia offers a perfect combination of history, culture, shopping, nature and relaxation, making your cruise stop an unforgettable experience.

Tortola Island
Tortola Island, a mountainous island of volcanic origin, is the largest and most populous of the British Virgin Islands. Once a place of refuge for buccaneers, today it is an ideal destination for all those who love unspoiled nature and water sports. Crystal clear waters, unspoiled nature and long beaches make the island's landscape unique. The crystal clear waters allow for numerous water sports such as snorkeling.
Get ready to wear your snorkel and mask to enjoy the beauty of the seabed and the animals that inhabit it. If you think that what I am saying is not enough, imagine diving into the waters of the island and seeing with your own eyes ancient shipwrecks, coral gardens and underwater mountains. Needless to say, this is an unforgettable experience that happens a few times in life.
One of the best ways to reach Tortola Island is aborad a cruise ship. Choose a cruise that depart from Tortola Island or that has the island as a stop is the ideal choice for those who want to discover the beauties of the island both during navigation and once you reach the island.

Philipsburg
Philipsburg is the capital of Sint Maarten in the Caribbean Sea. It is one of the best cruise ship ports in the Caribbean famous for shopping.
Philipsburg is the capital of the Dutch part of the island of St. Maarten, a Caribbean island divided into Dutch and French (Saint Martin). Business seekers flock to the duty-free shops and tax-free sales of the long Philipsburg shopping district. Visitors can also enjoy art galleries in the city, historical fortresses, casinos, and zoos, as well as Great Bay Beach and the boardwalk.