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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 cruising through turquoise waters or 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 launched around the world. 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 shrimp mac-n-cheese, “surfs up” tequila tacos, Cajun jambalaya, a full burger bar, and more. 

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

Bridgetown to Oranjestad - 7 Days

This is the Caribbean for those with a taste for something a bit more exotic. Colonial influences are still going strong here, from the “Little England” island of Barbados to still-very-Dutch Aruba, Bonaire, and Curaçao. Days ashore promise unexpected discoveries – a donkey sanctuary on Bonaire, underground rivers and caves in Barbados, a chocolate factory on Grenada, an artist colony on Curaçao. Beaches seem to shrug off the challenge of more northerly islands as they establish a standard of beauty all their own, swept by steady gust-free trade winds that make learning to windsurf a breeze. And between each eventful island, there is time to savor your surroundings – both on shore and on the decks of your elegant yacht.

Complimentary Private Event • Curacao: An Antillean Evening

Philipsburg to Colón - 7 Days

Begin your cruise where many leave off, at the extreme southern fringe of the Caribbean. Find hidden treasure in the historic Old Town of Cartagena and the emerald jungles of Panama. Immerse yourself in crystalline waters known for world-class diving and windsurfing. Explore charming pastel-colored towns. And enjoy a relaxed ambiance that perfectly compliments the yacht-style elegance of your Windstar ship.

Oranjestad to Puerto Caldera - 14 Days

So many vacations in one. Go diving in the marvelous ABC Islands, both Dutch and delightful. Make an epic passage through the Panama Canal. Penetrate the jungles of Colombia and Costa Rica in search of giant Blue Morpho butterflies, Resplendent Quetzals, and native cultures that live much as their ancestors did.

Complimentary Private Events • Isla de Coiba: Island Experience

San Juan to Bridgetown - 7 Days

Spend pampered days and nights in the secret hideaways of the Caribbean, kayaking off the Watersports Platform, walking on uncrowded beaches, and admiring sunsets reserved just for you. Linger on smaller islands where sea turtles nest and smiles are genuine. Learn how to say “amazing place” in Creole. Let nature and the Windstar staff fulfill every dream you’ve ever had about paradise.

Complimentary Private Event • St. Lucian Potpourri

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 cafés. 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

San Juan to San Juan - 10 Days

By departing from magical San Juan instead of from Florida, your Caribbean vacation begins earlier, on day one. And with ten days instead of the usual seven, you have time to take the full measure of this most iconic part of the Caribbean. Everywhere you look is another cover shot image. Dazzling white sand turns the shallows mesmerizing shades of peacock and mermaid, weathered fortresses point canons at long-vanished schooners, natural pools warm gently under the mid-day sun. On your private yacht, you’re equally at home in exclusive harbors and anchored off barefoot beaches, so you can see it all. Snorkel or dive on vibrant coral reefs. Follow your siren inland to rainforest adventures or duty-free boutiques. Thank your lucky Star Legend for bringing you here.

Complimentary Private Event • Prickly Pear Beach: 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

San Juan to San Juan - 7 Days

Begin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. Then explore Puerto Rico’s best-kept secret: the island of Culebra. It’s a natural paradise, home to one of the oldest bird sanctuaries in the United States and to Playa Flamenco, rated the third-best beach in the world. As you continue on this bewitching cruise through the Virgin Islands, no two days are alike. One day, you’re shopping chic French boutiques for the latest fashions from Paris. On another, snorkeling a secluded cove known only to lucky yachtsmen – like you. Skip more common and commercial ports like St. Thomas and Philipsburg in favor of less-visited destinations like Marigot and Montserrat. Bypass the major cruise terminals in favor of exclusive marinas and anchorages. And as guests on larger cruise ships take an excursion from Tortola to reach tiny Jost Van Dyke, your elegant yacht is already there.   

Complimentary Private Event • Prickly Pear Beach: Island Experience

Colón to Oranjestad - 7 Days

Discover the “deep south” of the Caribbean, beyond the mainstream cruises. The Dutch ABC islands acclaimed for their crystalline waters and world-class beaches, diving, and snorkeling. Seldom-visited mainland ports with a lively Caribbean vibe. And towns founded on Spanish gold that retain their colonial charm all these centuries later. It’s a voyage of discovery you won’t want to miss.

Complimentary Private Event • Curacao: An Antillean Evening

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