Beach Fun & Sun: A Remote Caribbean Getaway - Philipsburg, St. Maarten to Philipsburg, St. Maarten from Philipsburg, Sint Maarten, 19 Dec 2026 (7 nights)


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Cruise summary
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Your itinerary
Port descriptions and imagery are shown where available for each day or port.
Philipsburg is the capital of Sint Maarten, the Dutch side of the Caribbean island Saint Martin. Beachfront bars line the boardwalk along Great Bay. Voorstraat, or Front Street, has duty-free shops and casinos. The St. Maarten Zoo is home to parrots, monkeys and a playground. Sint Maarten Museum displays artifacts from the indigenous Arawak people. The ruins of 17th-century Fort Amsterdam stand on a nearby peninsula.
Gustavia is the main town and capital of the island of Saint Barthélemy. Originally called Le Carénage, it was renamed in honor of King Gustav III of Sweden.
Surrounded by many abandoned sugar mills, the small village of Falmouth is protected in a large horseshoe-shaped bay. Falmouth was the first settlement on Antigua set up by the British. Today Falmouth is a quiet village surrounded by old sugar plantations and mills with the main historic building of interest being St Paul's Church. The main center of activity in Falmouth Harbour is on the eastern side of the large horse-shoe bay where the shops, restaurants and marina are located.
Soper's Hole Marina is arguably one of the most picturesque anchorage in the British Virgin Islands.
Inviting beaches and tiny shops selling local treasures welcome you to this quiet island haven. Don't miss dining with your feet in the sand at Foxy's on the beach-a perfect lunch stop!
Inviting beaches and tiny shops selling local treasures welcome you to this quiet island haven. Don't miss dining with your feet in the sand at Foxy's on the beach-a perfect lunch stop!
The most chic resorts of the British Virgin Isles are located on Virgin Gorda, an eight-square-mile island divided nearly in two, with settlements at each end. The south of the island is best known for the curious assembly of house- sized rocks called “the Baths,” which are jumbled together to form huge underground pools and caverns. The beach at the Baths is large, wide, and sandy – perfect for sunning and swimming.
Philipsburg is the capital of Sint Maarten, the Dutch side of the Caribbean island Saint Martin. Beachfront bars line the boardwalk along Great Bay. Voorstraat, or Front Street, has duty-free shops and casinos. The St. Maarten Zoo is home to parrots, monkeys and a playground. Sint Maarten Museum displays artifacts from the indigenous Arawak people. The ruins of 17th-century Fort Amsterdam stand on a nearby peninsula.
What's included
Fare overview
This sailing is shown as a cruise-only guide fare with Windstar Cruises. The fare is linked to the ship, itinerary and cabin category you choose. Drinks packages, gratuities, Wi-Fi, flights, transfers and shore experiences are only treated as included where they are confirmed before booking.

Sailing aboard
Wind Surf
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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.
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