Windstar Caribbean

Windstar Cruises | Classic Caribbean: St. Maarten Roundtrip

Immerse yourself in the history of Charlestown, capital of Nevis, and Roseau, capital of the Caribbean Island nation of Dominica. Other ports of call include Pigeon Island, Les Saintes on Guadeloupe, Gustavia, and Basseterre.

Cruise Information: Classic Caribbean: St. Maarten to St. Maarten

Windstar Surf in St Lucia

X Windstar St. Maarten Rount trip Map

Cruise Itinerary: St. Maarten to St. Maarten

Cruise Day Cruise Port Description
Day 1: St. Maarten | Depart 7pm - at sea Embark on a delightful cruise and take a first wonderous step onto your yacht and unwind in a private suite.
Day 2: Charlestown, Nevis | Arrive 8am; Depart 5pm This capital of Nevis with its narrow streets and brightly painted Victorian and Georgian stone buildings is full of colonial history. Lovely Pinney’s Beach is nearby, with delightful sea turtles found along the beaches. Walk the main street and explore the Museum of Nevis History, St. Thomas Lowland Church, and the Nevisian Heritage Village.
Day 3: Roseau, Dominica | Arrive 8am; Depart 5pm Snorkel alongside brilliant parrot fish in the bubbly waters of Champagne Beach. Take a break and enjoy more than 150 species of plants and brilliant red-necked Jaco parrots at the botanical gardens. Explore the Boiling Lake and the Valley of Desolation at Dominica’s Morne Trois Pitons National Park, a UNESCO World Heritage Site.
Day 4: Pigeon Island | Arrive 8am; Depart 5pm The UNESCO World Heritage Site Pitons with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.
Day 5: Les Saintes, Guadeloupe | Arrive 8am; Depart 5pm 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 pristine blue waters.
Day 6: Gustavia, St. Barthélemy | Arrive 8am; Depart 10pm 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, shop for designer fashions, or sip the island’s signature “ti punch” as kite surfers fly by.
Day 7: Basseterre, St. Kitts | Arrive 8am; Depart 9pm 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: St. Maarten | Arrive 6am 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 several local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.
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