Classic Caribbean - Philipsburg, St. Maarten to Philipsburg, St. Maarten

The Classic Caribbean - Philipsburg, St. Maarten to Philipsburg, St. Maarten is a 7-night Caribbean cruise aboard Wind Surf, operated by Windstar Cruises. Departing Philipsburg, Sint Maarten on March 20, 2027, the voyage visits 7 ports. Fares start from $2,380 per person.

Length: 7 nights
Departs: Mar 20, 2027
Returns: Mar 27, 2027
Ports of call: 7

from $2,380

$340 / night per person, incl. taxes & fees

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Itinerary

Day 1 Mar 20, 2027 Philipsburg, Sint Maarten 13:00 – 19:00 6.0 hrs ashore 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. Philipsburg, Sint Maarten port guide Search cruises visiting Philipsburg, Sint Maarten

Philipsburg, Sint Maarten photo — Day 1 Mar 20, 2027 Philipsburg, Sint Maarten 13:00 – 19:00 6.0 hrs ashore 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. Philipsburg, Sint Maarten port guide Search cruises visiting Philipsburg, Sint Maarten

Day 2 Mar 21, 2027 Charlestown, Nevis 08:00 – 17:00 9.0 hrs ashore Get to know Nevis, one central volcano and an area five miles by seven, its circle island road less than a two-hour drive. Within that tiny space are crammed delights for every taste: a championship golf course at the Four Seasons; the exhilaration and romance of dashing across a beach on horseback; and a trek through a lush rainforest of bamboo and tropical fruit trees, entertainment provided by monkeys swinging through the branches. For history hunters there are a number of old sugar plantations in varying stages of preservation and decay. They have intriguing tales to tell, and perhaps a few ghosts for good measure.

Day 3 Mar 22, 2027 Roseau 08:00 – 16:00 8.0 hrs ashore 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. Roseau port guide Search cruises visiting Roseau

Day 4 Mar 23, 2027 Mayreau 08:00 – 17:00 9.0 hrs ashore Sip a tangy rum cocktail and leave your phone behind, as you sink into unbridled, undeveloped Caribbean bliss. An island gem of the Grenadines, Mayreau is the smallest island to house permanent residents, and a tiny gathering of just 200 are lucky enough to call it home. With limited infrastructure, and less than two square miles to explore, this is a place to enjoy the simple beauty of the here and now, as waves gently splash and the sun bronzes your skin. View less Dive spots invite you below the surface to a world of coral and tropical fish. Or you can stay put on Mayreau, to sprawl out across beautiful beaches like Saline Bay's - perhaps the island’s most enticing wedge of sand and tranquil blue waters. If that sounds too indulgent, earn your beachside bliss with a short hike up the small, densely-forested hill. You'll be rewarded with a great lookout across the other emerald islands, emerging from the azure seas. Jump aboard and hold on tight as your speedboat rips across the waves, or take a leisurely sailing tour of the surrounding islands of paradise. The glorious Tobago Cays are close by, and these uninhabited lands sparkle with a world of colour and sensory indulgence, immersing you in vistas lifted straight from the pages of a travel guide. Swim, snorkel, and let it all go.

Day 5 Mar 24, 2027 Les Saints 12:00 – 18:00 6.0 hrs ashore During the feast of All Saints in 1493, Christopher Columbus discovered this archipelago of nine islands that he named "The Saints". Today, only two of them are inhabited. Terre de Haut, in the east, is dominated by the Morne Mire hill; at the summit stands Fort Napoleon, paying homage to the islands' history. In the heart of the botanical garden, shared by iguanas and cacti, there is an exceptional view of the Baie des Saintes, one of the most beautiful in the world. The long shady beach of Pompierre, where it is forbidden to drop anchor, is a peaceful place for a swim, while Pain de Sucre Beach offers wonderful opportunities for snorkelling. On the island, don’t forget to taste the local speciality, the “tourment d’amour”, a cake made with coconut.

Day 6 Mar 25, 2027 Basseterre, St. Kitts 08:00 – 22:00 14.0 hrs ashore 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. Basseterre, St. Kitts port guide Search cruises visiting Basseterre, St. Kitts

Basseterre, St. Kitts photo — Day 6 Mar 25, 2027 Basseterre, St. Kitts 08:00 – 22:00 14.0 hrs ashore 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. Basseterre, St. Kitts port guide Search cruises visiting Basseterre, St. Kitts

Day 7 Mar 26, 2027 Gustavia, Saint Barthelemy 08:00 – 22:00 14.0 hrs ashore Cherry red roofs, yacht-sprinkled bays and a sophisticated French flavour all add to the gorgeous Caribbean allure of Gustavia. The island's capital rolls around a horseshoe-shaped harbour, where gleaming yachts hover and fancy boutiques, bars and restaurants fizz with life and clinking cutlery. Head up to red and white Gustavia Lighthouse to look down over the revered waters, which attract many a celebrity guest and diving enthusiast to these shores. View less Christopher Columbus was the first European to discover this volcanic island in 1493, giving it the name St Barthelemy in honour of his younger brother. The island has a unique history as a Swedish colony, following a deal with the French King Louis XVI to exchange the island with Sweden for better trading rights. It was returned to French control in 1878 and is now a French Overseas Collectivity. Learn more of the Swedish legacy at Fort Karl - which sits on a 29-metre-high hill above Shell Beach. The fort now lies in ruins, but you'll meet wandering iguanas, and the views down of sweeping sea and emerald coastline are some of the island's finest. Down below, a delightful spread of tiny pebbles and shell fragments are scattered like confetti and lapped by crystal-clear water. A little exploration uncovers countless other glorious beaches and natural wonders. Colombier Beach is a little out of the way but cradles silky-smooth sands and typically turquoise waters. If you have chance, find somewhere to settle and sip fruity rum cocktails as the sunset flares across the waves.

Pricing

Lowest fare we've tracked over the observed 94-day span: $2,380 · range $2,380–$3,199

Lower than 90% of peers This week-long sailing's from-price per night is lower than 90% of comparable sailings.

same cruise line, destination, duration, and departure window · from-price per night · as of Jun 27, 2026

Current prices

Per person · 2 guests · incl. taxes & fees

Inside

Not available

Oceanview

from $2,380

$340 / night

Fare rows

Stateroom

Cabin grade

Available

from $2,380

$340 / night

per person · incl. taxes

Deluxe Stateroom

Cabin grade

Available

from $2,555

$365 / night

per person · incl. taxes

Stateroom

Cabin grade

Available

from $2,695

$385 / night

per person · incl. taxes

Deluxe Stateroom

Cabin grade

Available

from $2,940

$420 / night

per person · incl. taxes

Balcony

Not available

Suite

from $5,285

$755 / night

Fare rows

Suite

Cabin grade

Available

from $5,285

$755 / night

per person · incl. taxes

Officers’ Suite

Cabin grade

Available

from $7,035

$1,005 / night

per person · incl. taxes

Prices verified Jun 27, 2026

Prices come from third-party data feeds via Windstar Cruises and may differ from the cruise line's current fare. Confirm the final price before booking. How our pricing works

Price history

30 days

○ = last available date (sold out, or no longer listed). · Price verified 20 hours ago.

Cabin grades

Oceanview

Lowest Oceanview $2,380 A Stateroom $2,695 AX Deluxe Stateroom $2,940 B Stateroom $2,380 BX Deluxe Stateroom $2,555

Suite

Lowest Suite $5,285 OS Officers’ Suite $7,035 STE Suite $5,285 TX Deluxe Stateroom

Lines step between recorded price changes. Plot up to 6 lines at once.

Show all 8 cabin grades

Cabin grades and pricing
Name	Supplier code	Type
Stateroom	A	Oceanview
Deluxe Stateroom	AX	Oceanview
Stateroom	B	Oceanview
Deluxe Stateroom	BX	Oceanview
Bridge Suite	BRS	Suite
Officers’ Suite	OS	Suite
Suite	STE	Suite
Deluxe Stateroom	TX	Suite

Ship

Your ship Wind Surf 4★ **14,745** GT **342** guests Built **1989** 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. Wind Surf ship guide Search cruises on Wind Surf

Similar cruises

Other sailing dates

Same itinerary, different dates. Prices per person · incl. taxes & fees.

Other available sailing dates
View	From pp	Departs
	from $4,060 $580 / night	Jan 23, 2027Voyage SU20270123-7D
	from $3,990 $570 / night	Feb 6, 2027Voyage SU20270206-7D
	from $3,570 $510 / night	Feb 20, 2027Voyage SU20270220-7D
	from $2,380 $340 / night	Mar 6, 2027Voyage SU20270306-7D

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