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Caribbean cruises to Philipsburg, Tortola, and St. Barts


St. Maarten to St. Maarten - 7 Days
Philipsburg, Falmouth Harbor, Soper's Hole, Jost Van Dyke, Virgin Gorda, Gustavia, Philipsburg
Experience the Caribbean’s private yachting scene during this voyage. Explore the quaint island charm of Soper’s Hole. At Jost Van Dyke, discover inviting beaches, charming shops and the famous Foxy’s as you overnight in the harbor. Sail to Virgin Gorda, with its assembly of house-sized rocks called “The Baths.” Savor the high life on St. Barts, with its 5-star restaurants, luxury resorts and boutiques.

Windstar Private Event
Prickly Pear Beach: Island Beach Party
You're invited to a private beach party – complete with sun, sand, entertainment, activities – and incredible food and drink.

During this event, for invited Windstar guests only, you'll be transported to lovely Prickly Pear Beach – an uninhabited nature refuge in the British Virgin Islands with a beautiful white sand beach and turquoise water.

You're on a spectacular secluded beach, so you can enjoy swimming in the warm Caribbean waters. Go water skiing or kayaking. If you're an avid snorkeler, don't miss this opportunity to see brilliantly colored tropical fish in crystal clear waters.

Feeling a little lazy? Grab a mat and just float. Otherwise, you can take part in our Windstar Beach Volleyball Tournament. Impress your friends with your eye for horseshoes, your skills on a large chess board, or your way with a bocce ball.

Lunch is fresh grilled local seafood plus amazing side dishes that will make your taste buds hum. Once sated, you'll return to your yacht with sweet memories of a day well spent. Ahhh. Another perfect day in paradise as a Windstar guest.
  • YEAR: 
  • 2014
  • 2015
  • Yachtsman’s Caribbean GO
800.258.7245