Windstar Cruises Caribbean: 14 nights from Philipsburg with Wind Surf
Jan 11, 2026

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.

Embark 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.

Cruises 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.

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.

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.

Saint 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.

Saint 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.

Saint 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.

The 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.

To 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.

Les Saintes

The Îles des Saintes, also known as Les Saintes, are an archipelago made up of eight small islands and rocks called Terre-de-Bas, Terre-de-Haut, Ilet Cabrit, Grand Ilet, La Coche, Les Augustins, Le Pate and La Redonde of which only two, Terre de Bas and Terre de Haut (the largest) are inhabited. Administratively, they are all dependent on Guadeloupe, in the French Antilles.

Les Saintes were discovered by Christopher Columbus in 1493, on All Saints' Day, and he consequently baptized them Los Santos, but the first French settlers who moved to the archipelago arrived only in 1643 from Brittany.

Roseau

Mayreau

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.

Fort de france

Fort 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!

The 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!

Castries

St Lucia is renowned for its beautiful beaches. The most popular is Vigie Beach, a beautiful curve of golden sand, dotted with swaying palm trees.

St. Lucia has been part of the British Commonwealth since 1803. But before that, it was often occupied by the French, whose influences are evident in much of the island's culture. Castries offers a colorful local market and great shopping. And the surrounding areas offer lush rainforests, impressive waterfalls, beautiful beaches and sulfur springs. Admire the beautiful coast of Santa Lucia from the deck of a catamaran. You will have an unbeatable view of the landscape and you will get an exhilarating ride.

Pigeon Island

Pigeon Island

Bequia

Set sail on an idyllic Caribbean escape from the enchanting island of Bequia. This serene and unspoiled gem in the Grenadines offers a tranquil and intimate starting point for your cruise. Experience the laid-back charm and pristine waters before embarking on a journey to discover secluded coves, vibrant coral reefs, and the untouched beauty of the Lesser Antilles, promising pure relaxation and natural splendor.

Mayreau

Saint George

Set sail on a delightful cruise from Saint George, Bermuda, a charming and historic town that is a UNESCO World Heritage site. With its pastel-colored buildings, narrow alleyways, and rich colonial past, Saint George offers a picturesque and tranquil departure point for your island escape. Experience the unique blend of British heritage and island serenity before embarking on a journey filled with sun, relaxation, and unforgettable Bermudan discoveries.

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.