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Caribbean


Candy-colored cocktails sipped in seaside watering holes. Carefree days followed by calypso-flavored nights. These are the siren songs that lure anyone with a yacht and a yearning to escape to the incomparable Caribbean Islands. Whether you’re sailing through turquoise waters, lazing on powdery white beaches, the glamorous harbors and unknown coves of this area remain a hidden treasure.

Introducing Island Experience 
Introducing our new Island Experiences in the Caribbean – part of the complimentary Private Event program launching around the world in 2015. These experiences seek to treat guests to the feeling of having their “own private island” for the day, with each Windstar Caribbean itinerary including an Island Experience Private Event. All Island Experience Private Events will offer fun in the sun beach and sport activities such as snorkeling, bocce ball, and volleyball with the chance to face the Captain and officers in a tournament. Indulge in the full beach barbeque with dishes including lobster and shrimp mac cheese, “surfs up” tequila lobster tacos, Cajun jambalaya, a full burger bar, and more. 

Philipsburg to Philipsburg - 7 Days

From the stunning drama of the Pitons to the captivating charm of Les Saintes. From hidden coves and secret beaches to exotic markets and lively cafĂ©s. Here’s the best of the Caribbean in one single voyage. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.

Complimentary Private Event • St. Lucia:Island Experience

Bridgetown to Bridgetown - 7 Days

This is the Caribbean of days gone by – deep blue waters, quiet coves, and tropical islands dotted with powdery beaches and lush green hillsides. Sail from the rugged natural beauty of St. Lucia to little-known isles that are off the tourist radar. From colorful Bequia and Mayreau in St. Vincent & the Grenadines to the open-air markets of exotic St. George’s, you’ll discover a part of the Caribbean that remains authentic and unspoiled. This is everything that makes the Caribbean synonymous with paradise.

Complimentary Private Event • Mayreau: Island Experience

Philipsburg to Philipsburg - 7 Days

Let us take you into hidden coves and tiny harbors no one else can reach as you fully experience the Caribbean’s private yachting scene. Explore the quaint island charm of Soper’s Hole and the inviting beaches of Jost Van Dyke 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.

Complimentary Private Event • Prickly Pear Beach: Island Experience

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