Itinerary

Day 1 Nov 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 Philipsburg, Sint Maarten port guide Search cruises visiting Philipsburg, Sint Maarten

Philipsburg, Sint Maarten photo — Day 1 Nov 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 Philipsburg, Sint Maarten port guide Search cruises visiting Philipsburg, Sint Maarten

Day 2 Nov 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. Gustavia, Saint Barthelemy

Day 3 Nov 22, 2027 St John's, Antigua 08:00 – 22:00 14.0 hrs ashore “One beach a day,” Antigua’s motto, refers to the island’s 365 beautiful beaches that are famous, secret or even set in volcanic craters. There’s a beach for every lifestyle, for those who are social and ones who seek solitude. When you arrive on an MSC Caribbean and Antilles cruise in the port of St. John’s, the capital and commercial centre of Antigua and Barbuda, embrace the city’s colourfully vi-brant houses dating to its British colonial period, along with the evocative white baroque towers of St. John's Cathedral, and the Fort James and Barrington fortresses. The laid-back cosmopolitan city, with its distinctly British flair, is renowned for its shopping at luxury boutiques and high-end shopping malls. Beyond the city, book an MSC excursion to the historic Nelson's Dockyard in English Harbour, dedicated to Admiral Horatio Nelson, who was stationed in the West Indies be-tween 1784 and 1787. The shipyard, a UNESCO World Heritage Site, is the largest of Antigua’s National Parks and still remains a working dockyard for numerous yachts and ships. Beautifully restored, its Georgian buildings in wood and stone date to the late 18th and early 19th centuries. Between April and the beginning of May, the Dockyard is the venue for some of the most important sailing regattas in the world, such as Antigua Sailing Week. The excursion continues on to visit the landmark ruins at Shirley Heights of-fering breath-taking vistas of English Harbour. If an excursion in nature appeals to you, head to Stingray City to swim with friendly southern stingrays in crystal-clear water. Or discover Antigua's lush rainforest from a bird's-eye perspective as you navigate through the treetops on a guided canopy tour that will have you walking over a suspension bridge and traversing zip lines over a spectacular gorge. St John's, Antigua St John's, Antigua port guide Search cruises visiting St John's, Antigua

St John's, Antigua photo — Day 3 Nov 22, 2027 St John's, Antigua 08:00 – 22:00 14.0 hrs ashore “One beach a day,” Antigua’s motto, refers to the island’s 365 beautiful beaches that are famous, secret or even set in volcanic craters. There’s a beach for every lifestyle, for those who are social and ones who seek solitude. When you arrive on an MSC Caribbean and Antilles cruise in the port of St. John’s, the capital and commercial centre of Antigua and Barbuda, embrace the city’s colourfully vi-brant houses dating to its British colonial period, along with the evocative white baroque towers of St. John's Cathedral, and the Fort James and Barrington fortresses. The laid-back cosmopolitan city, with its distinctly British flair, is renowned for its shopping at luxury boutiques and high-end shopping malls. Beyond the city, book an MSC excursion to the historic Nelson's Dockyard in English Harbour, dedicated to Admiral Horatio Nelson, who was stationed in the West Indies be-tween 1784 and 1787. The shipyard, a UNESCO World Heritage Site, is the largest of Antigua’s National Parks and still remains a working dockyard for numerous yachts and ships. Beautifully restored, its Georgian buildings in wood and stone date to the late 18th and early 19th centuries. Between April and the beginning of May, the Dockyard is the venue for some of the most important sailing regattas in the world, such as Antigua Sailing Week. The excursion continues on to visit the landmark ruins at Shirley Heights of-fering breath-taking vistas of English Harbour. If an excursion in nature appeals to you, head to Stingray City to swim with friendly southern stingrays in crystal-clear water. Or discover Antigua's lush rainforest from a bird's-eye perspective as you navigate through the treetops on a guided canopy tour that will have you walking over a suspension bridge and traversing zip lines over a spectacular gorge. St John's, Antigua St John's, Antigua port guide Search cruises visiting St John's, Antigua

Day 4 Nov 23, 2027 Deshaies 07:00 – 17:00 10.0 hrs ashore The port of Deshaies has a magnificent setting on the north-west coast of Basse-Terre Island, the western half of Guadeloupe. Nestling in the crook of a pretty bay on the Caribbean Sea, the village of wooden Creole-style houses extends along the foot of hillsides covered in tropical rainforest. Beyond the bay, the former property of famous French comedian Coluche is now a magnificent botanical garden where you can wander among West Indian trees and flowering plants and spot exotic birds. A little farther to the north is Grande Anse beach, one of most beautiful on the island. Deshaies Deshaies port guide Search cruises visiting Deshaies

Deshaies photo — Day 4 Nov 23, 2027 Deshaies 07:00 – 17:00 10.0 hrs ashore The port of Deshaies has a magnificent setting on the north-west coast of Basse-Terre Island, the western half of Guadeloupe. Nestling in the crook of a pretty bay on the Caribbean Sea, the village of wooden Creole-style houses extends along the foot of hillsides covered in tropical rainforest. Beyond the bay, the former property of famous French comedian Coluche is now a magnificent botanical garden where you can wander among West Indian trees and flowering plants and spot exotic birds. A little farther to the north is Grande Anse beach, one of most beautiful on the island. Deshaies Deshaies port guide Search cruises visiting Deshaies

Day 5 Nov 24, 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 Road Bay port guide Search cruises visiting Road Bay

Road Bay photo — Day 5 Nov 24, 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 Road Bay port guide Search cruises visiting Road Bay

Day 6 Nov 25, 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. Jost Van Dyke

Day 7 Nov 26, 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. Jost Van Dyke

Day 8 Nov 27, 2027 Virgin Gorda (BVI) 08:00 – 17:00 9.0 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) Virgin Gorda (BVI) port guide Search cruises visiting Virgin Gorda (BVI)

Virgin Gorda (BVI) photo — Day 8 Nov 27, 2027 Virgin Gorda (BVI) 08:00 – 17:00 9.0 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) Virgin Gorda (BVI) port guide Search cruises visiting Virgin Gorda (BVI)

Pricing

Lowest fare we've tracked over the observed 139-day span: $2,640 · range $2,640–$3,440

Lower than 86% of peers This week-long sailing's from-price per night is lower than 86% of comparable sailings.

same cruise line and duration · from-price per night · as of Aug 25, 2026 · Broader cohort: same cruise line and duration, compared by from-price per night.

Current prices

Per person · 2 guests · incl. taxes & fees

Inside

Not available

Oceanview

from $3,080

$385 / night

Fare rows

Stateroom

Cabin grade

Available

from $3,080

$385 / night

per person · incl. taxes & fees

Deluxe Stateroom

Cabin grade

Available

from $3,320

$415 / night

per person · incl. taxes & fees

Stateroom

Cabin grade

Available

from $3,440

$430 / night

per person · incl. taxes & fees

Deluxe Stateroom

Cabin grade

Available

from $3,720

$465 / night

per person · incl. taxes & fees

Balcony

Not available

Suite

from $4,040

$505 / night

Fare rows

Deluxe Stateroom

Cabin grade

Available

from $4,040

$505 / night

per person · incl. taxes & fees

Suite

Cabin grade

Available

from $6,040

$755 / night

per person · incl. taxes & fees

Officers’ Suite

Cabin grade

Available

from $8,040

$1,005 / night

per person · incl. taxes & fees

Bridge Suite

Cabin grade

Available

from $10,040

$1,255 / night

per person · incl. taxes & fees

Prices verified Aug 24, 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

Lowest fares with no residency, age, or service requirement — verify eligibility at booking. How our pricing works

Price history

30 days

We've tracked this sailing's fares every day for the past 141 days. Here's what each cabin type has cost.

Price history by cabin type
Cabin	Current	Lowest	Highest
Oceanview	$3,080	$2,640 · Jun 11	$3,440 · Jul 22
Suite	$4,040	$3,600 · Jun 11	$4,400 · Jul 22

Lowest and highest fares we've recorded for each cabin type · verified 19 hours ago.

○ = last seen (sold out or delisted). · Verified 19 hours ago.

Lowest fares with no residency, age, or service requirement — verify eligibility at booking. How our pricing works

Cabin grades

Lines step when the price changed; a gap means sold out or no public fare that day. Plot up to 6 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 Wind Surf ship guide Search cruises on Wind Surf

Similar cruises

Compare similar cruises

A Journey of Caribbean Adventure & Shimmering Tropical Harmony

EXPLORA III · Caribbean · 7 nights

from $3,680

$525 / night

per person · incl. taxes & fees

Oct 25, 2026

7 Night Southern Caribbean Cruise

Rhapsody of the Seas · Caribbean · 7 nights

from $1,198

$171 / night

per person · incl. taxes & fees

Sep 5, 2026

7 Night Southern Caribbean Cruise

Rhapsody of the Seas · Caribbean · 7 nights

from $834

$119 / night

per person · incl. taxes & fees

Sep 12, 2026

Eastern Caribbean with Puerto Rico

Regal Princess · Caribbean · 7 nights

from $911

$130 / night

per person · incl. taxes & fees

Sep 12, 2026

7 Nt Tortola, St. Maarten & Puerto Plata

Celebrity Beyond · Caribbean · 7 nights

from $848

$121 / night

per person · incl. taxes & fees

Sep 27, 2026

Eastern Caribbean with Puerto Rico

Regal Princess · Caribbean · 7 nights

from $705

$100 / night

per person · incl. taxes & fees

Sep 26, 2026

Browse all cruises in search →