Windstar Cruises Caribbean: 10 nights from Philipsburg with Wind Spirit
Jan 14, 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.

Roseau

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.

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!

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.

Charlestown

Virgin Gorda

Jost Van Dyke

During your cruise ship stop in Jost Van Dyke, you will discover a tropical paradise rich in adventure and relaxation. Start your day with a visit to White Bay, famous for its white sand and crystal clear waters. Relax under the palm trees, swim in the turquoise waters or snorkel to explore the vibrant marine life.

Don't miss the opportunity to visit Foxy's Tamarind Bar, a local institution where you can enjoy delicious Caribbean cocktails and typical dishes while listening to live music. For an unforgettable experience, take a boat trip to visit the spectacular caves of Norman Island.

If you are an adventure lover, take a short hike to the top of Jost Van Dyke to enjoy breathtaking views of the island and the surrounding sea.

Jost Van Dyke offers you a perfect mix of natural beauty, local culture and exciting activities, guaranteeing an unforgettable stop during your cruise.

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.

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.