14-night Caribbean cruise from Philipsburg, Sint Maarten on Wind Surf
The Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten is a 14-night Caribbean cruise aboard Wind Surf, operated by Windstar Cruises. Departing Philipsburg, Sint Maarten on February 6, 2027, the voyage visits 12 ports including Charlestown, Nevis, Roseau, Mayreau. Fares start from $6,692 per person.
Fixed editorial images from the places on this itinerary. They stay stable each time you return to this sailing.
Philipsburg, Sint Maarten
Offering some of the best vistas in all the Caribbean, St. Maarten is the smallest inhabited island in the world shared by two nations - France in the north and the Netherlands in the south. Dubbed the true melting pot of the Caribbean, the 37-square-mile island is home to people of 47 different nationalities and more than 400 restaurants, featuring a hugely diverse variety of cuisine.
The island also has two capitals: Philipsburg on the Dutch side, and Marigot in the French part. Once you arrive on an MSC Caribbean and Antilles cruise in St. Maarten, explore how the two cultures have blended their very distinct characters on one of our MSC excursions.
Your St. Maarten cruise will dock in Philipsburg, founded in 1763 by John Philips, a Scottish captain in the Dutch Navy. Philipsburg, with its pastel-coloured West Indian houses, is known for its duty-free shopping along Front Street, the Great Salt Pond, which once made the island literally “worth its salt,” and attracted the attention of the French, and Fort Willem, built in 1801, with mag-nificent views of the bay and the surrounding islands.
From there, several MSC excursions take you on a hilly drive to the French side of the island to experience Marigot. Originally a fishing village on a swamp for which it was named, Marigot became the capital during the reign of Louis XVI. Fort Louis, which overlooks Marigot Bay and Anguilla, was built in the late 18th century to protect the town’s warehouses of salt, coffee, sugar cane and especially rum from the English. Today, Marigot showcases quaint colourful gingerbread-like houses, tasty sidewalk bistros and a waterfront market selling fruit and vegetables, spices, local meats and fresh fish from Creole huts worth exploring.
For something special, spend the day on the Dutch side of the island at the restored sugar planta-tion at Rockland Estate. Take in a history lesson at the Emilio Wilson Museum or a nature hike and 360-degree views from Sentry Hill. Participate in a hands-on cooking demonstration of authentic local cuisines with lunch at Emilio’s restaurant, in an exclusive Martha Stewart excursion curated for MSC Cruises.
Also at Rockland Estate, thrill seekers can book other MSC excursions on the Flying Dutchman, a fast and furious zip line ride that will have you whizzing down the line at speeds of up to 56 mph (90 km) per hour. Then take the Pirate Sky Ride cable car back up the top to the Crow’s Nest where several platforms encircling the mountain afford panoramic views of the neighbouring islands of Saba, Sint Eustatius, Saint Barthélemy and Anguilla. Then plunge down the mountain on a Schooner Ride inner tube along a specially designed track.
To experience one of the island’s hottest spots and most popular attractions, visit the famous Maho Beach, also called Airplane Beach. Don’t get too comfortable, though. This is because you watch as planes pass only a short distance above your head as they land and take off from Princess Juli-ana Airport’s short runway next door.
Roseau
Discover Roseau, Dominica’s attractive capital that is entirely accessible on foot. A French outpost founded in the 16th century, it offers captivating landscapes with spectacular views of the Caribbean Sea, botanical gardens, colonial-style architecture and the impressive St. Patrick’s cathedral, all worth exploring on this MSC Caribbean and Antilles cruise.
In Dominica, nature reigns. Called the island of 365 rivers, the sound of water is nearly ever-present, beginning with the thermal springs around Roseau. Lush in vegetation, the volcanic origin of the island has created waterfalls, rivers and bubbling pools of hot water rich in minerals flowing from deep within the earth.
One MSC excursion not to miss is Hibiscus Falls, with an enchanting waterfall and beautiful pool where you can take a dip amid breath-taking nature. From there, your tour continues on through the central rainforest reserve to the Hibiscus eco-village, followed by a river tubing experience through some of the last and only remaining Carib Indian territory. Or take a guided hiking tour through the rainforest to Emerald Pool, an exquisite waterfall and pool that is among Dominica’s favourite gems.
For another natural wonder, take an MSC excursion to the impressive Titou Gorge, a natural crevice in the mountain that spouts hot and cold water at once. Scenes from “Pirates of the Caribbean: Dead Man’s Chest” were also filmed at the gorge. Then at Wotten Waven, relax in the natural hot springs. A long therapeutic soak in the mineral-rich waters will leave you feeling rejuvenated.
Looking for something offshore? Dominica is known for whale and dolphin watching. Board a catamaran on an MSC excursion for a chance to spot a dolphin, pilot whale, or a giant humpback whale. Or touch a live volcano as you snorkel above it in the marine reserve, feeling the sulphur heat escaping from the sea bed below.
Basseterre, St. Kitts
Columbus discovered St. Kitts (short for St. Christopher) and Nevis on his second voyage in 1493. Arawak and Carib Indians who had moved up through the islands from South America already inhabited both islands. While European immigrants massacred many of them, the Caribs continued to stage fierce battles, which became legendary. In 1632, the West Indies' first British settlement was established on the island, which soon developed into an important colony thanks to its sugar industry.
France and England shared St. Kitts for some time, but the partition ended with the Peace of Utrecht in 1713. After being declared a British colony in 1783, St. Kitts and Nevis, along with Anguilla and the British Virgin Islands, were administered as a single colony until 1871 when the Leeward Islands Federation was formed. This continued up to 1957 when St. Kitts and Nevis were granted self-government, with Britain remaining responsible for external affairs and defense. Both islands became an independent state within the Commonwealth in 1983.
Basseterre, St. Kitts' capital, still shows signs of colonial architecture. However, its setting against the emerald green hills ensures a distinct Caribbean ambiance. Many travelers agree that Basseterre is one of the prettiest of the Caribbean's small capitals.
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Follow the entire sailing from its first day to its last, with the route and schedule in one view.
Day 1·Feb 6, 2027
Philipsburg, Sint Maarten
Offering some of the best vistas in all the Caribbean, St. Maarten is the smallest inhabited island in the world shared by two nations - France in the north and the Netherlands in…
On any day, our 342-guest flagship, Wind Surf, the world’s largest sailing ship, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. During their cruise, you will find the perfect setting for ‘making an entrance’ in the beautiful reception area – and, appropriately, that’s only the beginning.
When you return to your stateroom, the luxury gets personal. Windstar’s signature bowls of flowers and fresh fruit will still be waiting for you, along with rich tufted headboards, soft seascape colors, beautiful new upholstery, and fine count Egyptian cotton linens welcome you to an oasis of relaxing indulgence.
Wind Surf recently underwent a significant renovation in November 2019 of public spaces and suites, including an expanded lounge with new lights and sound for upcoming stage performances. Relax into the destinations you’re visiting at the new World Spa by Windstar, which will offer regional spa treatments, including massage styles like Swedish, Japanese Shiatsu and Hawaiian Lomi Lomi. A new Officer’s Suite, which might be the only one of its kind, provides you the chance to stay in the heart of the officer quarters tucked right behind the Bridge.
Everything about Wind Surf speaks of welcome. Come aboard and see it for yourself.
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