Itinerary

Day 1 Jan 16, 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.

Day 2 Jan 17, 2027 Road Bay 08:00 – 18:00 10.0 hrs ashore Anguilla’s name is based on the word for eel in several Romance languages, and its 17-mile length and three-mile width are appropriate to the analogy. The northernmost of the Leeward Islands chain, it is a British overseas territory. With its resources largely limited to an abundance of breathtaking beaches and coral reefs, the island’s main industries are tourism and the lucrative cultivation of offshore banking and insurance tax havens. Road Bay and its village of Sandy Ground comprise the main harbor for ships on the island, although the entire coastline is scalloped with lovely coves and anchorages that make it a magnet for yachtsmen. The official currency is the Eastern Caribbean dollar, although U.S. dollars are widely accepted. They might be well-spent on a luncheon of impeccably fresh seafood from the surrounding seas. There are no less than seven shipwrecks strewn along the island’s barrier reefs, which have made it the wreck-diving capital of the region. Road Bay port guide Search cruises visiting Road Bay

Road Bay photo — Day 2 Jan 17, 2027 Road Bay 08:00 – 18:00 10.0 hrs ashore Anguilla’s name is based on the word for eel in several Romance languages, and its 17-mile length and three-mile width are appropriate to the analogy. The northernmost of the Leeward Islands chain, it is a British overseas territory. With its resources largely limited to an abundance of breathtaking beaches and coral reefs, the island’s main industries are tourism and the lucrative cultivation of offshore banking and insurance tax havens. Road Bay and its village of Sandy Ground comprise the main harbor for ships on the island, although the entire coastline is scalloped with lovely coves and anchorages that make it a magnet for yachtsmen. The official currency is the Eastern Caribbean dollar, although U.S. dollars are widely accepted. They might be well-spent on a luncheon of impeccably fresh seafood from the surrounding seas. There are no less than seven shipwrecks strewn along the island’s barrier reefs, which have made it the wreck-diving capital of the region. Road Bay port guide Search cruises visiting Road Bay

Day 3 Jan 18, 2027 Jost Van Dyke Arrives 19:00 Glowing turquoise waters, lazily bowing palm trees, and pristine white sand beaches – it's all waiting for you in Jost Van Dyke's picturesque Caribbean splendour. Slip off your shoes, you won't be needing them too much in these parts, as you wander soft, heavenly sands, and paddle out into impossibly clear waters. The island escape of choice for dallying yachts, which visit to soak up the off-the-beaten-path good life. Join them around the pristine beaches of this tiny celebrity magnet of an island. View less If this is your first experience of the Caribbean's splendour, you may be a little sceptical about the reality of those famed, shockingly bright colours that you see in photographs. If so, Jost Van Dyke will be love at first sight. Splash into water that glows with a bright teal hue and is blotched with occasional swells of deeper royal blue. Snorkellers will adore the explosions of colourful fish beneath the waves. White Bay is a slice of island perfection, with a neat hill of trees framing a sandy sweep of shaded beach bars. There's nothing for it but to indulge on a bed of soft pearly-white sand, and soak in the staggering beauty of it all. The wander up to Majohnny Hill is the most exertion needed to explore this four-square-mile island, and it's worth it to see the heavenly beaches emerging from tranquil waters below. Even the natural sea formations here encourage you to unwind, with waves gurgling and frothing over the rocks to create Bubbly Pool, a natural jacuzzi. Jost Van Dyke has a reputation as the off-the-radar island getaway of choice for celebrities like Keith Richards. A lot of that comes down to the calypso charm of its rustic beach bars - especially the legendary Foxy's Bar, which is run by island legend Foxy Callwood. Rum-drenched cocktails and icy buckets of beach beers await - sure to get you into the island’s party spirit in no time.

Day 4 Jan 19, 2027 Jost Van Dyke Departs 22:00 Glowing turquoise waters, lazily bowing palm trees, and pristine white sand beaches – it's all waiting for you in Jost Van Dyke's picturesque Caribbean splendour. Slip off your shoes, you won't be needing them too much in these parts, as you wander soft, heavenly sands, and paddle out into impossibly clear waters. The island escape of choice for dallying yachts, which visit to soak up the off-the-beaten-path good life. Join them around the pristine beaches of this tiny celebrity magnet of an island. View less If this is your first experience of the Caribbean's splendour, you may be a little sceptical about the reality of those famed, shockingly bright colours that you see in photographs. If so, Jost Van Dyke will be love at first sight. Splash into water that glows with a bright teal hue and is blotched with occasional swells of deeper royal blue. Snorkellers will adore the explosions of colourful fish beneath the waves. White Bay is a slice of island perfection, with a neat hill of trees framing a sandy sweep of shaded beach bars. There's nothing for it but to indulge on a bed of soft pearly-white sand, and soak in the staggering beauty of it all. The wander up to Majohnny Hill is the most exertion needed to explore this four-square-mile island, and it's worth it to see the heavenly beaches emerging from tranquil waters below. Even the natural sea formations here encourage you to unwind, with waves gurgling and frothing over the rocks to create Bubbly Pool, a natural jacuzzi. Jost Van Dyke has a reputation as the off-the-radar island getaway of choice for celebrities like Keith Richards. A lot of that comes down to the calypso charm of its rustic beach bars - especially the legendary Foxy's Bar, which is run by island legend Foxy Callwood. Rum-drenched cocktails and icy buckets of beach beers await - sure to get you into the island’s party spirit in no time.

Day 5 Jan 20, 2027 Virgin Gorda (BVI) 08:00 – 22:00 14.0 hrs ashore Local lore has it that the unusual shape of this little bit of paradise reminded Christopher Columbus of a reclining, voluptuous woman, so he named it Virgin Gorda, the "Fat Virgin." She is suitably adorned with dramatic heights that plunge down from Gorda Peak to the sparkling turquoise waters far below. This is a good place to explore in a jeep, swim with dolphins, or hike the rugged trails throughout the island. Virgin Gorda is most famous for The Baths, where giant granite boulders are strewn across the beach and in the water, creating pools, caves, and grottos – a sort of natural water park. Virgin Gorda (BVI) port guide Search cruises visiting Virgin Gorda (BVI)

Virgin Gorda (BVI) photo — Day 5 Jan 20, 2027 Virgin Gorda (BVI) 08:00 – 22:00 14.0 hrs ashore Local lore has it that the unusual shape of this little bit of paradise reminded Christopher Columbus of a reclining, voluptuous woman, so he named it Virgin Gorda, the "Fat Virgin." She is suitably adorned with dramatic heights that plunge down from Gorda Peak to the sparkling turquoise waters far below. This is a good place to explore in a jeep, swim with dolphins, or hike the rugged trails throughout the island. Virgin Gorda is most famous for The Baths, where giant granite boulders are strewn across the beach and in the water, creating pools, caves, and grottos – a sort of natural water park. Virgin Gorda (BVI) port guide Search cruises visiting Virgin Gorda (BVI)

Day 6 Jan 21, 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.

Day 7 Jan 22, 2027 Falmouth Harbour,Antigua 08:00 – 17:00 9.0 hrs ashore With 365 beaches to choose from, it's said that Antigua has a sandy escape for every day of the year. The sheltered twin bays of English Harbour hold an ever-alluring appeal and draw a beauty-seeking flotilla of yachts to drop anchor in their calm waters. Strap on scuba gear, crunch through paths of dense jungle, or soar up above to volcanic peaks in a helicopter - the choice is yours. Whether you seek adventure, or simply want to take it easy with a paperback and the song of the waves – a beautiful island of sun, sea, and sand lies before you. As the name implies, there's an unrestrained British Colonial influence here, and Horatio Nelson's name is imprinted deep into Falmouth's story. Walk in his footsteps at Nelson's Dockyards - the gorgeously restored, working Georgian dockyard. The colonial spirit is an evocative throwback to this important 17th-century Royal Navy base. Museums tell the story of the British exploits in the West Indies, and the life of Nelson - who lived here for three years. Clarence House is also close by, and the 200-year-old residence continues to draw visits from British royals to this day. This being Antigua, there's no shortage of jaw-dropping beaches and bathing opportunities. Take to pearly-white sands or explore the Pillars of Hercules – a set of smooth, rounded columns of rock that plunge dramatically into the waters below. Pigeon Point Beach is a ravishing amalgam of blues and pristine white sands, where turtles and stingrays glide through patches of coral reefs. Enjoy the best views of the naturally coddled bays of English Harbour by rising to Shirley Heights. Sunset is thrilling from this elevated vantage point, as reds and pinks spill across the skies.

Day 8 Jan 23, 2027 Philipsburg, Sint Maarten 06:00 – 07:00 1.0 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.

Pricing

Lowest fare we've tracked over the observed 85-day span: $3,199 · range $3,199–$3,599

Current prices

Per person · 2 guests · incl. taxes & fees

Inside

Not available

Oceanview

from $3,395

$485 / night

Fare rows

Stateroom

Cabin grade

Available

from $3,395

$485 / night

per person · incl. taxes

Deluxe Stateroom

Cabin grade

Available

from $3,605

$515 / night

per person · incl. taxes

Stateroom

Cabin grade

Available

from $3,710

$530 / night

per person · incl. taxes

Deluxe Stateroom

Cabin grade

Available

from $3,955

$565 / night

per person · incl. taxes

Balcony

Not available

Suite

from $4,235

$605 / night

Fare rows

Deluxe Stateroom

Cabin grade

Available

from $4,235

$605 / night

per person · incl. taxes

Suite

Cabin grade

Available

from $6,300

$900 / night

per person · incl. taxes

Officers’ Suite

Cabin grade

Available

from $8,050

$1,150 / night

per person · incl. taxes

Prices verified Jun 23, 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

Show all 8 cabin grades

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

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Beach Fun & Sun: A Remote Caribbean Getaway - Philipsburg, St. Maarten to Philipsburg, St. Maarten

Itinerary

Pricing

Current prices

Inside

Oceanview

Balcony

Suite

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Ship

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