Classic Caribbean
From the lush volcanic landscapes of Nevis Peak to the captivating charm of Les Saintes; hidden coves and secret beaches to exotic markets and lively cafés, you’ll discover the bes...
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Ports of Call & Itinerary
7-night voyage departing Philipsburg.
Printable Itinerary (PDF)Route Map
Classic Caribbean
7 ports plotted · click a marker for details
Day 1
Philipsburg , Sint Maarten (Dutch part)
Sunday, 09/01/2028
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 restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.
Day 3
Roseau , Dominica
Tuesday, 11/01/2028
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 Lake and the Valley of Desolation at Dominica's Morne Trois Pitons National Park, a UNESCO World Heritage Site.
Day 4
Mayreau Island , Saint Vincent and the Grenadines
Wednesday, 12/01/2028
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 airports, no banks, and only one small village (Old Wall) perched on a hillside.
Day 5
Terre-de-Haut , Guadeloupe
Thursday, 13/01/2028
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 6
Basseterre, Saint Kitts , Saint Kitts and Nevis
Friday, 14/01/2028
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 7
Gustavia , Saint Barthélemy
Saturday, 15/01/2028
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 8
Philipsburg , Sint Maarten (Dutch part)
Sunday, 16/01/2028
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 restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.
Room Type & Prices
All prices per person based on double occupancy. Solo traveller prices — single occupancy. Contact our cruise experts for the latest availability and best fares.
Category B
188 sqft · Up to 2 guests
Category BX Deluxe
188 sqft · Up to 2 guests
Category A
188 sqft · Up to 2 guests
Category AX Deluxe
188 sqft · Up to 2 guests
Category TX Deluxe
188 sqft · Up to 2 guests
Suite
376 sqft · Up to 3 guests
Broadmoor Suite/Sea Island Suite
495 sqft · Up to 3 guests
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Your Ship
Wind Surf
Windstar's Flagship Sailing Yacht
As part of our Wind Class, our 342-guest Wind Surf offers a sailing experience like no other — one with real working sails.