Caribbean Cruises


Hidden Harbors. Private Beaches.
Island-Hopping in Private Yacht Style.


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.


 

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. Discover the best of this region with one single Caribbean cruise. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.

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 and relax on this Caribbean cruise.

Bridgetown to Bridgetown - 8 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. On this Caribbean cruise you will 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 Destination Discovery 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 on this Caribbean voyage. And as guests on larger cruise ships take an excursion from Tortola to reach tiny Jost Van Dyke, your elegant yacht is already there.   

Philipsburg to Bridgetown - 7 Days

Experience the perfect mix of traditional Caribbean charms and the delightfully unexpected. Stroll the seaside promenades of Antigua’s historic Nelson’s Dockyard and colorful St. George’s, Grenada — known as the most beautiful harbor in the Caribbean. Walk barefoot on crescent beaches in every shade of pink, white and charcoal. Meet proud Carib Indians and Montserrat’s famously friendly residents. Discover sea horses and trumpet fish dodging geothermal bubbles in Dominica, and an eerie underwater sculpture park in Grenada. Wake each morning thinking nothing could top the previous day on this Caribbean cruise, until it does.

San Juan to San Juan - 10 Days

By departing from magical San Juan instead of from Florida, your Caribbean cruise 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 Philipsburg - 7 Days

Rest your eyes on scenes straight out of your favorite pirate movies as Star Breeze explores the Leeward and Windward Islands. Watch the dramatic twin Pitons grow as you approach St. Lucia. Explore the natural pools and smooth granite boulders of Virgin Gorda’s The Baths. Jump from the Watersports Platform into the warm azure waters off St. Bart’s. Explore weathered stone fortresses, Victorian gingerbread houses, Creole cafés, and all the amenities of your lovely yacht on this Caribbean cruise.

Bridgetown to Colón - 7 Days

Travel deep into the Southern Caribbean to Aruba and beyond, to less-visited islands and the treasures of the Spanish Main. Days at sea are thoughtfully interspersed with days in charming Southern Caribbean favorites. Go horseback riding on a white-sand beach in Aruba. Ride a horse-drawn carriage through Cartagena's Old City past bougainvillea-covered balconies and open-air barbershops. Return to your Windstar yacht for a deck barbecue with a view that puts gold bullion to shame.

*Please note that the November 25, 2017 voyage includes an extra day at sea in place of a stop at Bequia, St. Vincent & the Grenadines.

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