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.


 

Bridgetown to Bridgetown - 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.

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. 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 on this bewitching Caribbean cruise where 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.   

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.

Bridgetown 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 the botanical park in Deshaies, 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 10 days instead of the usual 7, you have time to take the full measure of this most iconic parts 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 ship, 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 Pride for bringing you here.

Colón to Bridgetown - 7 Days

If you love sailing, this is your voyage, as the tall white sails of your Wind Star ship and warm trade winds create a truly relaxing luxury Caribbean cruise. Your sailing ship 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 Bequia rested, relaxed and ready for a hike up Mount Pleasant. Conclude your voyage in charming Bridgetown, with its UNESCO sites and magical Harrison's Cave.

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. 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.

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 Puerto Caldera - 18 Days

Enjoy three extraordinary vacations in one: A Caribbean beach escape, a historic Panama Canal transit, and a Costa Rican rainforest adventure. Watch Wind Star’s billowing white sails unfurl as you sail between small-ship exclusives like Bequia and Mayreau. Join the parade of ships entering the Panama Canal, with plenty of room on deck and quick access between vantage points. Step off a Zodiac onto a private beach fragrant with roasting barbecue and bursting with possibilities. And discover Costa Rica’s incredible biodiversity as you hike deep into the rainforest with thick humus muffling your footsteps and undiscovered species tantalizingly close.

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, Colombia, 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.

Lisbon to St. Maarten - 20 Days

Days of bliss crossing the Atlantic are followed by the carefree spirit of the Caribbean. You can look forward to doing what you want when you want all under the care of your ship’s attentive crew. Order room service for breakfast in bed or find a quiet corner to curl up with your book and drift to sleep with the rocking of the ship. Arrive in St. John’s refreshed and energized to introduce yourself to each unique port of call. You’ll want to keep a journal to savor your memories of pristine beaches, sparkling clear waters, friendly people and charming towns like Gustavia and Les Saintes enough to beckon you back another time.

Bridgetown to Bridgetown - 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. Barthélemy, St. Lucia’s Pigeon Island and much more.

Ditch the rushed cacophony of everyday life for a more relaxed tempo that leaves you in Lisbon feeling rested and refreshed. This 3-week cruise through the Caribbean and across the Atlantic is the perfect means of reconnecting with friends and loved ones during relaxing sea days and unforgettable shore excursions. Take a scenic drive to Harrison’s Cave near Bridgetown.  Snorkel the clear waters around St. George’s or Bequia, and watch the dramatic twin Pitons grow as you approach St. Lucia. When you arrive well rested in Lisbon, you’ll be ready to wander Moorish castles, sample rich red port wines and take in the busy seagoing sites along Portugal’s historic Tagus River.

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 Colombia and Panama.

Find the best of the worlds of relaxation, discovery and travel. Let yourself unwind on the transatlantic days at sea, reading, taking advantage of the WindSpa and Fitness Center amenities, making new friends and feasting on new culinary delights and personal favorites. Arrive in Barbados refreshed and ready to discover the wonders the Caribbean Islands invite you to experience. Find the UNESCO sites of Historic Bridgetown and the Garrison, full of historical significance. Let the nutmeg aroma fill your senses as you wander the spice markets of Grenada, Discover the graceful flamingos on the beaches of Bonaire and pick your favorite carved door in Aruba. Come on a journey of do as you please when you please and create authentic and unforgettable experiences along the way.

The easiest way to forget your work obligations and daily routines is an epic 21-day transatlantic vacation that begins with Spanish architecture and white Caribbean sands and eventually lands in Lisbon, Portugal. Intermingle days at sea with Southern Caribbean favorites like the flamingoes and divi-divi tress of Aruba, the Spanish flair of Cartagena and the spectacular view from Bequia’s Mount Pleasant. After crossing the Atlantic, charter a tour of Lisbon and a ride up one of the city’s famous yellow funiculars to the sweeping views in Bairro Alto, high above the Portuguese city. This unforgettable crossing is a perfect way to arrive refreshed and ready for Europe.

San Juan to San Juan - 14 Days

Whether you’re passionate about swimming among rarely seen undersea wildlife or the intricate cultures and intertwined European histories of the Windward Islands, this 2-week cruise offers the best combinations of charm, island heritage and natural beauty. Shop unique designer apparel in St. Barts, where you’ll discover a fashionable confluence of high-end brands normally associated with places like Madison Avenue, but displayed in an ambiance that’s anything but intimidating. Stare in wonder at the glow from miniscule bioluminescent organisms stirred by your kayak paddle during a tour of the Fajardo Bio Bay nature reserve near San Juan. Master the art of cooking with distinct spices like nutmeg, cloves, and allspice in authentic Caribbean cuisine while taking direction from a highly-skilled native chef in Philipsburg. This Caribbean getaway is the perfect duration for lovers of island life and those who want to spend more time exploring the Windward Islands overlooked by other cruise lines.

Bridgetown to Oranjestad - 7 Days

Blue waters, gentle trade winds and warm sunny days are natural hallmarks of Southern Caribbean cruises, but this memorable journey offers a delicious range of options for vacationers seeking a rich variety of activities. Snorkel among rays, batfish and sea turtles in the clear waters off Bequia or dive deeper with air tanks among coral reefs and vibrant parrotfish off the remote jungle shores of Bonaire. When you work up an appetite, satiate your sweet tooth with a delicious tour of the Diamond Chocolate Factory in Grenada, where you’ll also learn about the cultivation of essential spices like cocoa, vanilla and nutmeg. Or take advantage of one of the many in-port cafés serving up regional dishes like rice and peas, slow-roasted Pernil and spicy jerk chicken. Whether you’re looking for warmer beach destinations closer to the equator or a refreshing change-up from the popular Windward Island Caribbean ports, this weeklong Windstar getaway exceeds expectations with immersive excursions, exceptional meals and personalized service that goes beyond what you’ll find on other cruise lines.

Oranjestad to Puerto Caldera - 11 Days

Experience one of the seven wonders of the modern world and one of the most important accomplishments in human civilization during this memorable, 11-day cruise of Central America featuring a complete transit of the Panama Canal in broad daylight. As you transit 48 miles of the busiest and most historic waterway in the world, an onboard guide will point out both natural and man-made wonders along the Panama Canal, covering the history of the early overland routes, initial attempts by the French and the eventual success by Americans, and ongoing enhancements and maintenance. On the Pacific side you’ll learn about unique rainforest wildlife and biodiversity from expert local naturalists in remote, pristine reserves like Isla Parida, Panama and Manuel Antonio National Park, Costa Rica. This cruise through first-world wonders and primeval splendors offers the freedom to see and experience far more under the sun.

San Juan to San Juan - 7 Days

Revel in seven days of surf, sand and sunsets during this leisurely cruise up and down the Caribbean’s Windward Islands. It’s a perfect vacation getaway for anyone craving a quick escape from life’s everyday obligations. Swim among sea turtles and glide above dazzling coral reefs with a highly skilled diving guide off the coast of Les Saintes’ volcanic shoreline. Stroll the weather-beaten parapets of the citadel of El Morro near San Juan, Puerto Rico and run your fingers along the stone scars left by Dutch invasions and American bombardments. Then clip into a zip line and hang on as moss-covered limbs and colorful wild birds rush by your head as you glide through St. Lucia’s rainforest canopy. Vacation time is always well spent among the Windward Islands, but nothing makes it more perfect than the personalized attention and unique excursion opportunities offered by Windstar.

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