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Philipsburg, Sint Maarten

14 nights · Caribbean

14-night Caribbean cruise from Philipsburg, Sint Maarten on Wind Surf

The Star Collector: Caribbean Explorations is a 14-night Caribbean cruise aboard Wind Surf, operated by Windstar Cruises. Departing Philipsburg, Sint Maarten on February 27, 2028, the voyage visits 12 ports including Falmouth Harbour,Antigua, Road Bay, Soper's Hole, Tortola, British. Fares start from $4,228 per person.

Length
14 nights
Departs
Feb 27, 2028
Returns
Mar 12, 2028
Ports of call
12

Voyage code SU20280227-14D

from $4,228 pp

via CruiseDirect

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Why this route stands out

A closer look at the journey

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.

Road Bay

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.

Virgin Gorda (BVI)

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.

Price tracking

Today’s fare, in context

Price history

30 days
Fare details

Fare details

Per person · taxes & fees included
Current fares
Verified 3 days ago
Oceanview
$4,228
Suite
$5,572
Tracked range
156 days
Price history by cabin type
CabinCurrentLowestHighest
Oceanview $4,228 $4,172 on Jul 25 $5,303 on May 10
Suite $5,572 $5,516 on Jul 25 $6,743 on May 10
Cabin grades
8 total
StateroomOceanview · A
Deluxe StateroomOceanview · AX
StateroomOceanview · B
Deluxe StateroomOceanview · BX
Bridge SuiteSuite · BRS
Officers’ SuiteSuite · OS
SuiteSuite · STE
Deluxe StateroomSuite · TX

○ = last seen (sold out or delisted). · Verified 3 days ago.

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Current prices

Per person · 2 guests · incl. taxes & fees

Inside

Not available

Oceanview

from $4,228

$302 / night

Fare rows

Stateroom

Cabin grade

Available

from $4,228

$302 / night

per person · incl. taxes & fees

Deluxe Stateroom

Cabin grade

Available

from $4,536

$324 / night

per person · incl. taxes & fees

Stateroom

Cabin grade

Available

from $4,704

$336 / night

per person · incl. taxes & fees

Deluxe Stateroom

Cabin grade

Available

from $5,096

$364 / night

per person · incl. taxes & fees

Balcony

Not available

Suite

from $5,572

$398 / night

Fare rows

Deluxe Stateroom

Cabin grade

Available

from $5,572

$398 / night

per person · incl. taxes & fees

Suite

Cabin grade

Available

from $8,876

$634 / night

per person · incl. taxes & fees

Officers’ Suite

Cabin grade

Available

from $11,676

$834 / 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

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The journey

14 nights, in order

Follow the entire sailing from its first day to its last, with the route and schedule in one view.

Philipsburg, Sint Maarten

Day 1 Feb 27, 2028

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…

Explore Philipsburg, Sint Maarten

Day by day

The full itinerary

16 scheduled calls
Wind Surf

Your ship

Wind Surf

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.

4★ 14,745 GT 342 Passengers Built 1989
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from $4,228 pp

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