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.


 

St. Maarten to St. Maarten - 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.

St. Maarten to St. Maarten - 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.

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 Caribbean 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 in favor of less-visited destinations like Montserrat. Bypass the major cruise terminals in favor of exclusive marinas and anchorages on this Caribbean cruise. And as guests on larger cruise ships take an excursion from Tortola to reach tiny Jost Van Dyke, your elegant yacht is already there.   

St. Maarten 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

Colón to St. Maarten - 7 Days

If you love sailing, this is your voyage, as the tall white sails of your Wind Star yacht and warm trade winds create a truly relaxing luxury Caribbean cruise. Your sailing yacht is yours to do as you please. Unwind on deck in the intoxicating freedom of sailing every day. Drop by the Bridge to plot your course on the navigation charts. Try an inspired wine pairing in AmphorA. Arrive in Antigua rested, relaxed, and ready for rainforest or snorkeling adventures, then conclude your voyage in Dutch St. Maarten where France is just a short borderless drive away.

Bridgetown to St. Maarten - 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 on this Caribbean cruise.

*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.

Bridgetown to Bridgetown - 14 Days

Enjoy two weeks indulging in the yachting lifestyle as you explore new ports each day throughout the delectable Leeward and Windward Islands from either Barbados or St. Maarten. Visit more enticing places with no repeat ports over the course of your voyage, and stay late into the evenings allowing for in-depth adventures. Point the bow to yachting favorites like Pigeon Island, St. George’s, and Bequia. Go places that appear on very few Caribbean cruise itineraries like the modern-day Pompeii of Montserrat. Enjoy Windstar's exclusive Signature Beach Barbecue at Prickly Pear Beach on Virgin Gorda, where mangroves and hiking trails augment the pristine beaches of this National Park.

Bridgetown to Puerto Caldera - 14 Days

Escape the crowds and island traffic congestion as you rediscover the old charm of the Caribbean’s lesser-known locales in this delightfully intimate cruise through Southern Caribbean Islands, Columbia, Panama and Costa Rica. As your cruise progresses, the charming remote white beaches and quaint village markets give way to tropical jungles, the Panama Canal and the Pacific Ocean. As you turn north up the coast, you’ll visit Panama’s breathtakingly beautiful Isla Parida, and Costa Rica’s mist-shrouded cloudforest near the ecotourism epicenter of Quepos.

St. Maarten to St. Maarten - 14 Days

Skip the usual Caribbean cruise stops and discover the small harbors, overlooked havens and most remote secrets among the Leeward Islands. Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Barbuda, Soper’s Hole in Tortola, Gustavia in St. Barthémy, St. Lucia’s Pigeon Island and much more.

St. Maarten to Colón - 14 Days

You earned this. Stretch out in the sunshine, savor your citrus-topped liquid refreshment and listen as the trade winds gently whisper through the palm fronds above your head. In addition to relaxing on legendary white sand beaches and sampling far too many frozen concoctions to count, you’ll hop down to the southernmost and warmest waters on this Caribbean cruise, stopping off in sun-drenched Aruba and exploring the untouched natural splendors in Columbia and Panama.

Lisbon to St. Maarten - 21 Days

Today’s hurried pace and air travel prevalence overshadow the romantic and easy pace of crossing the Atlantic by luxury yacht. Rekindle the romance of a classic ocean voyage and follow the trade routes of seafarers and adventurers bound for the New World on this transatlantic cruise from historic Lisbon, Portugal to tropical St. Maarten. Once you arrive in the Caribbean, your Windstar captain sets a course among the southern island havens and highlights, with stops at the best beaches in the world.

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