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.

Bridgetown to San Juan - 7 Days

Trade your down-filled comforter for a bright beach towel during this weeklong cruise up the Windward and Leeward Islands from Bridgetown, Barbados to San Juan, Puerto Rico. Whether you’re eager for new adventures or simply want a relaxing beach and a rum punch, this journey melts winter doldrums. Ride an electric tram deep into underground chambers near Bridgetown and discover waterfalls, bubbling streams, towering stalagmites and daunting stalactites. Observe endangered Hawksbill sea turtles as they are rehabilitated at the Old Hegg Turtle Sanctuary in Bequia. Sample sweet green figs or fried plantains in a St. Lucia open market, or savor pork hocks among the small cafés in the port capital of Castries. Paddle a glass-bottom, two-person kayak through the turquoise shallows surrounding the remote archipelago of Les Saintes in Guadeloupe. Discover the convenience and visual clarity of Snuba snorkeling among vibrant gobies, squirrelfishes and surgeonfishes off South Friars Beach in Basseterre. Shop for unique handcrafted rings, bracelets and necklaces, summer-ready beachwear, or simply sip an iced coffee in Gustavia on St. Barts. Before your week wraps up, you’ll land at Virgin Gorda, where you can relax at nearby bays and beaches, or elevate your heartrate with an invigorating hike up to the scenic summit of Virgin Gorda Peak. At the end of your week you’ll land at San Juan, the capital of Puerto Rico. Shop Old San Juan, explore the elegant and historic La Fortaleza governor’s house or take in the local artistic works and historic artifacts at several museums.

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.

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.

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.

San Juan to Bridgetown - 7 Days

Uncurl your frozen toes as you escape the winter doldrums during this week-long cruise featuring sundrenched beaches and steamy tropical rainforests along the Lesser Antilles Islands in the Caribbean. Set sail from the colorful Colonial Era homes and shops in San Juan, Puerto Rico, then roam like the untethered horses across the tiny island of Vieques, wandering barefoot on beige sandy beaches, or delving deep into the shady, tropical recesses of the Vieques National Wildlife Refuge. Gleaming white sands, sparkling turquoise waters and Philipsburg’s vibrant pastel buildings offer respite from the starker winter hues up north this time of year, but if you’re seeking culinary adventures, the delicious saltfish fritters, meat-filled pastries and potent and refreshing fruity Le Planteur punch will certainly compete for your attention. Learn about the future plans for Montserrat’s newly-developed capital in Little Bay, or visit the ghostly past among the dusty ruins of the Buried City, where former homes remain entombed in volcanic ash. Glide among geothermal bubbles and schools of flitting angelfish, blue tang, yellow goatfish, and blue-striped grunts just off the sloping shores of Roseau’s Champagne Beach. Soar into the treetops in an open-air gondola ride, taking in Pigeon Island’s rare avian and arboreal wonders high above a rainforest reserve. Master SCUBA diving in the company of expert divers or venture inland and sample delicious organic gourmet chocolate at a cocoa processing facility near St. Georges in Grenada. Your adventure concludes in Bridgetown, Barbados, where you can reflect upon memories and deeper thoughts in the quiet shadows of explore the Gothic-inspired, St. John’s Church, or find the perfect surf conditions during a drive up the scenic Gold Coast.

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.

New York City to San Juan - 11 Days

This 11-day, southbound journey crosses 23 degrees of latitude to tropical islands where the average temperature difference between winter and summer can be less than 10 Fahrenheit degrees. Not long after Manhattan’s glowing skyline slips beyond the horizon, you arrive at the northernmost point in your journey: Newport, Rhode Island. It’s home to Vanderbilt mansions and warm and creamy lobster bisque, hundreds of sailboats, and the International Tennis Hall of Fame. From here you turn south and be the first cruise ship to transit the thriving Chesapeake & Delaware Canal. Take your own walk around the angular, pocked walls of Fort McHenry, a pentagonal-shaped fortification that inspired Francis Scott Key’s The Star Spangled Banner. Float past the immense Naval Station Norfolk in Virginia, the largest naval base in the world, and walk the storied battleship deck of the USS Wisconsin. Warmer breezes rise as you approach Bimini’s blue waters, a favorite fishing haunt and drinking destination for writer Ernest Hemingway. Swim along a quiet beach near Samana in the Dominican Republic, or search for rare birds and animals along the mangroves in Los Haitises National Park. Your final destination is just a day away among San Juan’s vibrantly painted buildings and the brooding, weathered walls of Castillo San Felipe del Morro. Nearby you’ll find sandy beaches and lively cantinas to help you completely forget about the encroaching winter months ahead.

Oranjestad to Bridgetown - 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. And between each eventful island, there is time to savor your surroundings – both on shore and on the decks of your elegant ship.

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.

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.

Colón to San Juan - 7 Days

History buffs, beach bums and xenophiles will all find something to celebrate on this unique itinerary to Central America and the Caribbean. Discover the barely inhabited tropical islands and friendly Guna Yala villagers of the San Blas Islands. Step back in time to the days of the Spanish Empire as you visit five of the oldest cities in the Americas. Explore forts pockmarked by time and cannon balls. Encounter pirate lore as you dive the wreck of Captain Kidd’s ship off Island Catalina. And relive it all over mofongo and rum in Old San Juan.

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.

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 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.

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 captivating charm of Les Saintes.  Take the scenic drive to Harrison’s Cave in Bridgetown. Discover weathered stone fortresses, Victorian gingerbread, Creole cafés, and all the amenities of your lovely ship. 

Bridgetown to St. Maarten - 8 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.

Vancouver to San Juan - 39 Days

Take the full measure of the Americas as you explore North America’s vibrant West Coast, Central America’s man-made and natural wonders, and South America’s colonial and pre-Columbian legacy. Dine and sip your way down the U.S. West Coast, treating your palate to fine wines, flavorful microbrews and tastebud-thrilling Baja Med cuisine. Discover amazing nature sanctuaries from Jacques Cousteau’s favorite Sea of Cortez to Costa Rica’s wildlife-rich jungles. Cross the Panama Canal as only a small ship can, with the great gates looming up above. And investigate everything from Mayan ruins to colonial capitals, breathtaking beaches to remote Indian villages.

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.

Bask among the Caribbean’s favorite beaches and attractions before relaxing on a transatlantic crossing so you’re rested and ready for European excursions. Throttle up as tropical greenery and natural beauty sweep past your ATV near Monterrat’s Foxes Bay. Float down a refreshing river on a tube near Roseau, Dominica. Dive among coral, crab, cowfish and clown wrasse in a pristine marine reserve with professional guides near Casteries, St. Lucia. Lift a paddle blade as you explore St. George’s unclouded coastal waters in a clear-bottomed kayaking adventure. Stroll the halls of Pagerie Habitation near Martinique’s Anse Mitan, the former childhood plantation of Empress Josephine before she left for France and married Napoleon. Board a private sailboat bound for a remote bay for secluded swimming and snorkeling paired outside of Les Saintes, Guadeloupe. With so many excursions available, this cruise is a perfect way to transition into the relaxing days during your crossing to Lisbon, Portugal.

Bridgetown to Bridgetown - 14 Days

Enjoy two weeks indulging in the yachting lifestyle as you explore new ports each day throughout the delectable Caribbean Islands from Barbados. Visit more enticing places 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 two of  Windstar's exclusive Signature Beach Parties and two Signature Onboard Barbecues.

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.

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 Les Saintes, Anse Mitan, 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.

San Juan to San Juan - 14 Days

Indulge your passion for nature as you seek out unique wildlife among the more than 170 bird species in the Vieques National Wildlife Refuge, or glide high into the trees in an open-air gondola above a Pigeon Island rainforest reserve on St. Lucia. Take SCUBA lessons in St. George’s, then swim with sea turtles and schools of gleaming fish, or snorkel through a myriad of ascending geothermal bubbles off Champagne Beach in Dominica. Browse one-of-a-kind handmade jewelry, local artwork and unique island apparel in the brightly-painted shops of Old San Juan, Puerto Rico. Take in trendy boutiques and find that perfect silk top or summer dress in Gustavia, St. Barts. Sip tangy, rum-infused fruit cocktails among the effervescent nightlife of countless cantinas or find your own secluded corner of a quiet beach for extended moments of reflection. No matter how you decide to explore, every moment of this memorable Antilles adventure is time well spent.

Montreal to San Juan - 23 Days

The sugary, cinnamon sweetness of a doughy beavertail pastry overwhelms your taste buds as you stroll along the cobblestones throughout Old Montreal’s Parisian-themed shops, cafes and brasseries. Relax on a scenic horse-drawn carriage ride or savor buttery-rich lobster among Bar Harbor’s brightly painted boutiques and galleries. Amble along New York’s Central Park serpentine paths, or take in the skyline from a departing Staten Island Ferry bound for the Statue of Liberty. Sample regional wines from Long Island, Finger Lakes, and Hudson River Valley in a Manhattan wine shop. Brush the gray armor plating of USS Wisconsin’s imposing 16-inch guns on Virginia’s Elizabeth River, or admire more than 450 fragrant rose flowers at the Norfolk Botanical Garden. Then relax and break out your shorts and light cotton shirts for the sea days leading up to the warm beaches and mangrove mysteries in Bimini and Samaná. Your journey culminates in San Juan’s Old City, within walking distance of El Morro’s scarred fortress walls. Wander the storied streets where traders plied their wares or made idle chatter about the tobacco trade and worrisome pirates. Order a potent rum drink at a raucous neighborhood pub or request a fruit cocktail from a quiet, sundrenched table overlooking the harbor. It’s a perfect way to cap the unforgettable experiences on this extensive Atlantic Seaboard odyssey.

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.

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.

Oranjestad to St. Maarten - 14 Days

There is no better remedy for winter blues and early spring fever than this 14-day cruise throughout the Caribbean’s best southern ports and beaches. Ride horses in the Aruba surf. Sip cactus liqueur at a one-of-a-kind Bonaire distillery. Explore the Hato Caves on Curaçao, which were former 200,000-year-old coral reefs long before the island’s earliest human inhabitants transformed them into primitive homes. Dive among vibrant schools of fish off Grenada at Boss Reef or Purple Rain Reef, or take a SCUBA lesson in St. George’s warm waters. Sail off in a catamaran to a Tobago shopping getaway at the village of Scarborough. Golf 18 holes on the green fairways of Cap Estate near Castries, the only golf course on St. Lucia. Paddle a clear-bottom kayak on a guided tour through the scenic waters off Les Saintes in Guadeloupe. Throttle up on 4-wheel ATVs through cane fields and country dirt roads near St. Kitts. Swim with tame dolphins not far from Virgin Gorda. This remarkable Caribbean cruise concludes in Philipsburg, St. Maarten, where you can tour former America’s Cup sailboats, browse city art galleries and studios, or sit back at a cool café and sample spicy, smoky island creole cuisine like jambalaya, or pair a chilled fruity rum cocktail with warm memories of new friends.

St. Maarten to St. Maarten - 10 Days

Ten days in small ports, countless opportunities for sunny Caribbean cruise memories among blue waters, beckoning beaches and delicious dishes. View the pyroclastic powers of the Soufriere Hills Volcano among the gray abandoned ruins of Plymouth, Montserrat’s former capital. Snorkel among millions of volcanic bubbles and dozens of tropical fish near the shores of Champagne Beach in Roseau. Dive among dolphins near Martinique’s tiny port of Anse Mitan. Swim or kayak among Atlantic blue tang, green sea turtles and spotted eagle rays in the azure waters off Guadeloupe’s calm coastlines of Les Saintes. Seek out perfectly shaped seashells or shop for island haute couture beneath the red, terracotta-tiled roofs of trendy Gustavia on St. Barthélemy. After 10 delightful days your cruise concludes among Philipsburg’s pastel-painted shops, cafés and colorful history. Rum and cool corners are plentiful, so you and loved ones can relax and recount your treasure trove of new vacation memories.

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