VINCENT VACATIONS
7 NIGHTS | WINDSTAR | WIND SURF

7-Night Classic Caribbean Cruise

Aboard Wind Surf (Windstar) | Departing St Maarten (Philipsburg) to St Maarten (Philipsburg) | 1 Available Departures from $3,132

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7 NightsDuration
WindstarCruise LineWind SurfCruise ShipSt Maarten (Philipsburg)Embarkation PortCaribbean EasternRegion
$3,132Starting Fare
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Upcoming Sailings & Stateroom Fares (1)

Departure DateReturn DateInsideOceanviewBalconySuitePerks & Action
Dec 26, 2026
Sailing #1610554
Jan 02, 2027Call for Exclusive Rate$3,132Call for Exclusive Rate$3,972
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PORT-BY-PORT TIMELINE

Day-by-Day Cruise Itinerary

Classic Caribbean Route Map
Day 1

PHILIPSBURG, ST MAARTEN (SXPHI)

Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole

Day 2

GUSTAVIA, ST BARTHELEMY (BLGUS)

Affectionately known as St. Barts, the Caribbean's most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island's signature ti punch as kite surfers fly by.

Day 3

CHARLESTOWN (KNCHA)

This capital of Nevis with its narrow streets and brightly painted Victorian and Georgian stone buildings is full of colonial history. Alexander Hamilton lived here as a child and you can see the ruins of the Hamilton Estate. Lovely Pinney's Beach is nearby and a group of volunteers work at night ta

Day 4

ROSEAU, DOMINICA (DMRSU)

Get ready for a full day with plenty to do. Snorkel alongside brilliant parrot fish in the bubbly waters of Champagne Beach. Take a break to enjoy more than 150 species of plants and brilliant red-necked Jaco parrots at the botanical gardens. If you're up for an optional hike, don't miss Boiling Lak

Day 5

MAYREAU (VCMA6)

Mayreau is the smallest inhabited island of St. Vincent and the Grenadines, covering just about 1.5 square miles with a population of only a few hundred people. Tucked between Union Island and the Tobago Cays in the southern Grenadines, it's known for its laid-back, off-the-grid charm—there are no a

Day 6

LES SAINTES, GUADELOUPE (GPLSS)

This is the Caribbean as you've always imagined it, with yacht-filled harbors set against volcanic mountains and endless stretches of palm-fringed beach. The underwater world here attracted the likes of Jacques Cousteau, but even novice snorkelers will enjoy exploring these impossibly blue waters.

Day 7

BASSETERRE, ST KITTS (KNBAS)

With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean's small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.

Day 8

PHILIPSBURG, ST MAARTEN (SXPHI)

Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole

COMPLIMENTARY EXTRAS

Available Promotions & Onboard Credits

Reduced Deposit

One or more fares on this sailing includes a reduced deposit promotion.