Caribbean Cruises

Hidden Harbors. Private Beaches.
Island-Hopping in Windstar 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.

Cozumel to St. Maarten - 11 Days

Cruise through the Greater Antilles discovering magical places that fell off the map and tiny gems that were never on it in the first place. Skip the crowds of Montego Bay and Ocho Rios and head instead for the silver screen beauty of Port Antonio, “discovered” by Errol Flynn and then long forgotten. Enjoy the retro-Caribbean vibe of Grand Cayman and the undersea wonderland of La Romana. Sink into the sand on perfect white beaches, dive to pirate shipwrecks, swim beneath waterfalls wrapped in jungle and fall in love with a Caribbean you didn’t know still existed.

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

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 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 ship is already there.

St. Maarten to St. Maarten - 6 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 island charm of Road Town 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.

St. Maarten to St. Maarten - 11 Days

Set a course for warm island adventures packed with inland excursions and underwater explorations during this 11-day cruise that conveniently begins and concludes in Philipsburg, St. Maarten. Jump in an open-air 4x4 and ride to Ti Tou Gorge on Dominica, one of the few volcanic crater lakes in the Caribbean. Snorkel or SCUBA dive among schools of reef fish and sea turtles off the coast of Bequia. Learn how nutmeg and chocolate were harvested and processed a century ago before sampling highly rated “Jouvay” chocolate near St. George’s on Grenada. Delve into the shadowy caverns of Harrison’s Cave and explore colossal chambers, underground waterfalls and towering stalagmites. Ride a fast speedboat from Les Saintes and relax on the warm remote shores of Pain de Sucre Beach. Sip tropical drinks as you relax on rattan furniture during a scenic ride along an old narrow-gauge railway that transported sugar cane to Bassetèrre mills on St. Kitts decades ago.

San Juan to Miami - 10 Days

Bask in the sun, glide with sea turtles and sample spicy-hot Caribbean cuisine and unforgettable seafood dishes during this 10--day Caribbean cruise with memorable stops in Puerto Rico, the British Virgin Islands, St. Barthélemy, St. Maarten, Dominican Republic, Turks and Caicos, and Key West, Florida. Cast off from Virgin Gorda on a sleek catamaran bound for a remote marine park reef rich in mesmerizing schools of vibrant tropical fish. Seek out green sea turtles and other sea life from glass windows in a semi-submersible vessel off the coast of St. Barthélemy. Browse the brightly painted, Old World colonial shops and sample delicious Caribbean seafood cuisine along the scenic and lively boardwalk at Soper’s Hole on Tortola, and the largest Margaritaville in the Caribbean at Grand Turk. Linger ashore long after sunset during an overnight stay in Key West, Florida, where you can spend an afternoon wandering the vacation homes of Ernest Hemingway and President Harry S. Truman before dining and dancing at casual beachside nightclubs or hanging out bathed in the orange neon glow of Sloppy Joe’s Bar.

Bridgetown to Bridgetown - 7 Days

Discover the warmth of scenic island splendors paired with delicious Caribbean cuisine during this 7-day cruise from Barbados to Dominica, Montserrat, St. Barthélemy, Antiqua, Guadeloupe, and St. Lucia. Swim or snorkel surrounded by brightly colored tropical fish off the shores of Roseau, or stay inland and amble amid Dominica’s most stunning and fragrant flowers at several placid botanical gardens. Meander between historic colonial houses in Nelson’s Dockyard east of Falmouth Harbour, or trek along nearby trails to higher vistas above Antiqua, where British frigates and sloops anchored below centuries ago. Stroll the cobbled streets of Les Saintes, then snack on spongy and sweet tourment d’amour pastries within sight of pastel-hued Saintoise wood fishing boats bobbing in the palm-lined harbor. Glide in an open-air gondola among vibrant tropical birds nestled amid Pigeon Island’s shady rainforest canopy as a naturalist offers insights about the unique characteristics of St. Lucia’s Caribbean oceanic forests.

Bridgetown to Oranjestad - 7 Days

Those who love watersports, snorkeling and diving will be on Cloud 9 on this cruise through the Windward and ABC islands. Swim with vibrant fish and friendly sea turtles as you visit ports in Tobago Cays Marine Park, in Bonaire National Marine Park, and in the proposed Speyside Marine Protected Area. Paddleboard right from the Watersports Platform as we visit smaller ports and less-visited bays away from the crowds. And when you’ve had your fill of ocean action (if you ever do), head to shore and explore colorful Dutch colonial harbors, sugar-white beaches and mouthwatering island cuisines.

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 St. Maarten - 10 Days

Explore the Leeward Islands of the Caribbean from panoramic summit views to sunny seashores and beneath azure waves during this 10-day cruise. Swim with gentle Antiqua stingrays near Falmouth Harbour. Take in expansive views of Martinique from the summit of Fort de France and admire colorful flowers in the quiet shade of small port Anse Mitan’s botanical garden. Learn how to crush local cocoa nibs into liquefied chocolate during a delicious chocolatier class in Castries on St. Lucia. Sail on a swift catamaran beyond Soper’s Hole and across turquoise waters to Norman Island, a lush and sandy setting that inspired Robert Lewis Stevenson’s classic Treasure Island. Extend your British Virgin Island shore explorations to include succulent lobster, grilled tuna and sweet rum cocktails during overnight port stays in Jost Van Dyke and Virgin Gorda. Remain comfortably dry while viewing colorful reef fish and coral during a semi-submersible cruise near Gustavia.

San Juan to San Juan - 4 Days

A perfect vacation solution for busy schedules, this 4-day cruise visits some of the most famous island stops in the Caribbean, including St. Barthélemy, Jost Van Dyke, Virgin Gorda, and San Juan, Puerto Rico. Stroll the shadowy, crenelated ramparts of Fort San Felipe del Morro or sip fiery golden rum at a distillery near San Juan’s thriving harbor. Dine on fresh-caught swordfish and grilled mahi-mahi at a beachside cafe or sample authentic French Creole dishes at a family-owned bistro. Sail on a catamaran from St. Barthélemy to the Marine Park at Colombier Bay and snorkel amid vibrant schools of reef fish, or dive deep with professional SCUBA guides off the coast of the British Virgin Island. Swim and play with friendly dolphins at Road Town near Jost Van Dyke. Wander the intricate, surf-carved passages in The Baths, steep granite boulders strewn among Virgin Gorda’s clear tidal pools and white sands.

Miami to Colón - 10 Days

Combine Caribbean fun with Central American culture on this remarkable 10-day cruise that stretches from Florida to the landmarks and lesser-known small ports along the coastlines of Mexico, Belize, Honduras, Columbia, Costa Rica, and Panama. It’s a balanced blend of exciting activities and cultural experiences offering enlightening insights. Uncover little-known facts about Key West’s famous resident writers, including Robert Frost, Tennessee Williams, and Ernest Hemingway, or sail to the Dry Tortugas National Park on a fast catamaran for an afternoon of snorkeling among vibrant coral reefs, skeletal shipwrecks, and old nautical artifacts. Swim between stalagmites during a guided exploration of Rio Secreto, an underground river system, or take in the view from the top of an ancient Mayan pyramid at the prominent Cobá archaeological site. Clutch a comfy floatation device as you float down Belize’s Cave Branch River and into the shadowy recesses of ancient Mayan caves. Take a trip to a working Honduran farm in Campamento and sample a farm-to-table meal with a local Honduran family. Hike to a rainforest waterfall for a refreshing swim near Trujillo. Scan the treetops and dense undergrowth in Cahuita National Park for sloths, coatis, and iguanas. Snorkel and sunbathe off Red Frog Beach near the small port of Bocas del Toro in Panama, or board a boat for a short voyage to Bird Island where you can observe colorful tropical birds and coastal marine life. This exceptional journey ends near the Old Quarter of Colon, where you can shop for Panamanian souvenirs or make a trip to Embera Quera, an indigenous community living off the grid along the leafy banks of Gatun Lake on the Panama Canal.

Bridgetown to Colón - 11 Days

Venture from Colombia to the quiet solitude of the Caribbean’s southern islands during this 11-day cruise. Explore a restored Spanish colonial house and master the art of professional Colombian coffee tasting during a delicious tour near Cartagena’s Old City. Ride mountain bikes along centuries-old Aruban donkey trails near Oranjestad. Feed ostriches, cradle massive ostrich eggs, or trace your fingers along ancient coral walls inside the Hato Caves near Willemstad on Curaçao. Search for pelicans, blue herons and pink flamingos among the mangroves in Lac Bay National Park near Kralendijk on Bonaire. Dive among schools of reef fish in turquoise waters off the coast of Grenada or dine on local Creole shellfish with plantain-rich mangú, spicy rice and island lager in St. George’s. Sail away to remote, white-sand beaches or shop among locals in Union Island’s authentic fruit market near Bequia on St. Vincent & the Grenadines.

St. Maarten to Colón - 10 Days

Pastel Dutch colonial towns, long-legged pink flamingos, turquoise grottoes… everywhere you turn the colors of the Caribbean catch your eye. Watch cliff divers leap into sapphire waters from St. Bart’s pink seashell beach, Anse de Grands Galets. Snorkel with blue tangs, iridescent parrotfish and butterfly fish over the reefs of Bonaire. Ride a horse and carriage past bougainvillea-covered balconies in Cartagena. Each new port is a fresh canvas for your memories.

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 cannons 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.

Oranjestad to Colón - 9 Days

Bougainvillea-covered balconies, jungles teeming with wildlife ... there’s more treasure here than the Spanish ever dreamed of. Step back in time to Spain’s colonial heyday in Cartagena and Santa Marta, where museums glitter with pre-Colombian gold and jewelers display fresh-from-the-mine emeralds. Join the birds in the rainforest canopy and caimans in thick mangroves. Dine alfresco beneath a colony of stars and toast the perfect antidote to winter.

St. Maarten to Bridgetown - 7 Days

Enjoy the perfect mix of must-see Caribbean towns and harbors off the beaten path as you cruise and sail the royal beauties of the Lesser Antilles islands. Explore colonial history in pastel waterfronts, weathered forts and former sugar plantations. See the Caribbean at its most wild and beautiful on Dominica, St. Lucia and St. Kitts. Join the jetsetters on St. Barts, and make a rare visit to Montserrat, the “Pompeii of the Caribbean.” And everywhere you go, find delicious white beaches that turn rose and orange under Caribbean sunsets.

New York City to San Juan - 11 Days

Venture from the cosmopolitan Big Apple to warm Bermuda beaches and the picturesque Caribbean shorelines of Grenada, St. Barts, St. Kitts, and the British Virgin Islands during this 11-day cruise. Kayak amid gliding sea turtles and radiant tropical fish, explore pastel-hued Bermuda shops, and dine on traditional codfish dishes, spiny lobster and seared tuna steaks during an overnight stay in Hamilton. Sample aromatic nutmeg and rich chocolates on a flavorful Grenada spice factory tour. Measure your progress on a St. George’s foodie and history walking with frosty Piña Coladas, citrusy painkillers, and varied rum punches during your overnight port stay. Shop for one-of-a-kind jewelry or distinctly classic island casual wear at St. Bart boutiques in Gustavia. Sunbathe and snorkel near the golden sands and green hills defining iconic South Friars Bay near Basseterre. Dance, dine and savor the company of good friends and attentive crew at Windstar’s exclusive Signature beach party on Virgin Gorda.

Combine a relaxing, two-week transatlantic crossing with six wondrously warm days among bright Caribbean beaches, dense rainforests, colorful reefs and a generous supply of delectable tropical cocktails. Swim with dolphins at Prospect Reef’s natural lagoon near Soper’s Hole. Pilot your own two-person rigid inflatable boat along the scenic Sir Francis Drake Waterway near Jost Van Dyke. Stay out late shopping among Virgin Gorda’s beachside stalls, wander Mustique’s exclusive and uncrowded sandy shores, or swim and snorkel offshore among vibrant fish and coral prior to relaxing with sweet, rum punch cocktails. Sail a catamaran from Gustavia to the colorful reefs teeming with gorgeous tropical fish and gracefully gliding sea turtles. Summon your courage to zipline and transit teetering suspension bridges during a race across the Open Course Canopy Challenge high among gnarled branches, tropical birds and lush rainforest leaves near Falmouth Harbor.

Escape the ordinary during this 14-day adventure that spans the Lesser Antilles islands and ventures into uncrowded cays and uncongested ports accessible exclusively to small ship cruising. Spin and swirl in the gentle currents of a rainforest river as you take a tubing adventure near Roseau on Dominica. Skim Antiqua’s azure waves and soar above famed reefs, hotels, and beaches during a helicopter tour from Falmouth Harbor. Search for wild horses amid the remote hills of Cas En Bas during a St. Lucia hike. Inhale the heady fragrances of countless tropical flowers at a scenic botanical garden near Anse Mitan on Martinique. Grab your snorkel mask and set sail from Mayreau on St. Vincent to the remote beaches of Mopion, an uncrowded stretch of white-sand beach and vibrant reef surrounding a cay that many herald as “the Caribbean’s smallest island,”—a perfect secluded haven for swimming amid curious tropical fish.

St. Maarten to St. Maarten - 17 Days

Escape on an extraordinary cruise rich in decadent island adventures throughout the Caribbean’s Leeward Island chain. Visit Hamilton House, a modest stone building and birthplace of Alexander Hamilton, and stroll the lush grounds of Nesbit Plantation, the beachside estate of Fanny Nesbit, who would meet and marry the future naval hero, British Admiral Horatio Nelson on Nevis Island. Go with the flow on a river tubing adventure in refreshing tropical river currents near Roseau. Soak in the rusticness of Les Saintes before exploring the glamour of St. Kitts and St. Barts.  Sail along Martinique’s scenic north coast on a fast-moving catamaran, or ride inland by Jeep to sample rum at a distillery near Anse Mitan. Delve into the cool caverns of Harrison’s Cave in Barbados, surrounded by subterranean streams and waterfalls. Master the delicious art of crushing cocoa beans and making chocolate in Castries or Pigeon Island on St. Lucia. Sample tropical punches during overnight stays in both Jost Van Dyke and Virgin Gorda.

St. Maarten to Bridgetown - 21 Days

Embrace extraordinary experiences exclusive to small ship cruising during this three-week exploration of the Caribbean’s Lesser Antilles island chain. Swim with dolphins during an extended overnight stay in Jost Van Dyke in the British Virgin Islands. Savor African, European, and Indian ingredients and influences in popular Caribbean dishes as you sample spicy regional cuisine in the Fairview Great House on St. Kitts. Tour the Montserrat Volcano Observatory and learn how plant and animal life recover after volcanic eruptions, then see firsthand at the Montserrat National Trust Amerindian Gardens near Little Bay. Float above colorful coral reefs in clear-bottom kayaks as you glide through the pristine blue waters of Les Saintes on Guadeloupe. Hang onto halyards and winch handles as you master sailing a 40-foot racing yacht on scenic Rodney’s Bay near Pigeon Island on St. Lucia. Wander the 18th century grounds of the childhood home of Empress Josephine, Napoleon’s future wife, as you uncover historic French colonial life on Martinique.

St. Maarten to Bridgetown - 14 Days

Discover less-traveled roads and concealed refuges throughout the Caribbean on this 14-day cruise that blends iconic destinations and little-known shorelines like a favorite beachside cocktail. Search for green sea turtles and watch iridescent fish flit among sunken freighter wreckage from the dry side of a porthole in a Gustavia-based, semi-submersible. Sail past St. Kitts uncrowded southeast shores before slipping silently beneath the surface to snorkel among exotic fish and colorful coral. Savor sweet, shredded coconut cakes washed down with local sun rum amid Fort Napoleon’s cool shadows above Les Saintes, Guadeloupe. Meet local artists at St. Lucia’s Rodney Bay Village and rediscover your creative brushstrokes in an island scenery painting class. Raise the sails on a catamaran outbound from Mayreau to quiet Saline Bay for uncrowded hours of swimming and sunbathing. Relax in the Balthazar River’s swirling currents as you float in tubes through a shady tropical forest on Grenada.

Combine a classic Atlantic Ocean crossing with unforgettable visits to Caribbean small ports, Lisbon’s Gothic landmarks and the gateway to the Panama Canal during this far-ranging, 25-day cruise between Central America and Portugal. Gaze out from the crenelated battlements of Lisbon’s Belém Tower, a Tagus River fortification that greeted returning Portuguese seafarers for centuries. Curl up with a favorite book while planning a week’s worth of massages and indulgent spa treatments during your Atlantic crossing. Swim, snorkel or SCUBA among vibrant aquatic wildlife at the Bonaire National Marine Park. Taste the shredded beef, cumin-infused richness of Colón’s Ropa Vieja, a unique and popular breakfast and dinner meal throughout this busy Panama Canal seaport.

Bridgetown to Oranjestad - 14 Days

Begin in Barbados with a visit to the fairyland magic of Harrison’s Cave before setting sail for the French-Caribbean splendor of Martinique, where Empress Josephine spent her childhood. In St. Lucia enjoy shopping in the bustling capital of Castries, scenic Morne Fortune, and an overnight on Pigeon Island with plenty of beach time and a chance to visit the majestic volcanic Pitons. Follow your nose through the aromatic open-air markets of beautiful St. George’s on the “Isle of Spice.” Enjoy the exclusive Signature Beach Party on Mayreau and walk up Mount Pleasant to witness the amazing view from Fort Hamilton on Bequia. Swim with sea turtles in Tobago Cays Marine Park and listen for the conch beckoning fishing boats home. In Soufriere, feel the heart and soul of St. Lucia when you stroll by street vendors and hike to secluded waterfalls. Bonaire begs you to bring binoculars for bird watching — from flamingos to native parakeets to Amazon parrots. Savor the pastel colors of Old Town Willemstad and explore the limestone formations and ancient petroglyphs of Hato Caves. Complete your voyage in Aruba where you can relax and take in some of the Caribbean’s best beaches or play dominoes with locals.

Begin in Colón by exploring the engineering wonder of the Panama Canal. In Bocas del Toro, soak up the laidback atmosphere and colorful clapboard houses before heading to Isla San Andres to swim with puffer fish and sea turtles at the UNESCO Biosphere Reserve. Snorkel and kayak with dolphins in the ocean playground of Roatan, and sample baleadas and pastilles with delicious Honduran coffee. Visit the howler monkey sanctuary in Belize City and explore the ancient Mayan ruins of Chacchoben on Costa Maya. Discover Cozumel’s Chankanaab, an eco-park with underwater caverns home to dolphins, manatees, and sea turtles.Experience Grand Cayman’s energetic art scene, with over 250 practicing artists. Explore Cayman Brac’s island-long bluff with caves, secluded beaches, and lush forests, and reach for the incredible Reach Falls from Port Antonio, Jamaica. Visit the Caribbean’s oldest city and largest botanical garden in Santo Domingo In Virgin Gorda, swim in the underground pools known as “The Baths,” and complete your journey with Dutch treats and French delicacies in the “Cuisine Capital of the Caribbean,” St. Maarten.

St. Maarten to St. Maarten - 13 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.

St. Maarten to St. Maarten - 18 Days

White sands, rum cocktails and glorious tropical sunsets await you during this 18-day exploration of the Caribbean’s most iconic destinations with overnights in Jost Van Dyke and Virgin Gorda. Swim and snorkel amid colorful reef fish and tiny bubbles rising from a sea floor volcanic vent during an off-shore snorkeling adventure to Champagne Reef near Roseau, Dominica. Browse unique shops and relax on sandy beaches on Mustique, an exclusive island near Bequia. Bask in the warm sun while gazing at bright fish swimming beneath your clear-bottom kayak in Les Saintes in Guadeloupe. Perfect your French cooking skills in the kitchen of a respected restaurant overlooking Grand Case on Anguilla. Discover how perfumes are made and create your own special essence near Philipsburg on St. Maarten. Swim with friendly dolphins in a natural lagoon near Soper’s Hole in Tortola. Take the helm of a two-person rigid inflatable boat and explore the bays and inlets of the Sir Francis Drake Waterway near Jost Van Dyke.

Dive right into adventure in the underwater caverns of Cozumel’s Chankanaab eco-park — home to dolphins, manatees, and sea turtles. Then set sail for Isla Mujeres to wander the Mayan Temple of El Meco and Hacienda Mundaca ruins. On Grand Cayman, experience Stingray City, where you can feed and touch these mystical creatures. Explore Cayman Brac’s island-long bluff with caves, secluded beaches, and lush forests, and visit the marine life of Reach Falls from Port Antonio, Jamaica. Stroll the Caribbean’s oldest city and largest botanical garden in Santo Domingo, and discover white-sand beaches ringed by coral reefs on Isla Catalina. In Virgin Gorda, swim in the underground “Baths,” and sample Dutch and French culture in St. Maarten. Barbuda brings its signature pink sand while Roseau offers snorkeling in the bubbly waters of Champagne Beach. On Pigeon Island take in the Pitons volcanic peaks and discover the distinctive French charm of Les Saintes with an underwater world that’s attracted the likes of Jacques Cousteau. Visit Brimstone Hill Fortress National Park in lovely Basseterre and the chic island of St. Barts (look for celebrities). Return to St. Maarten, the Cuisine Capital of the Caribbean, for one last treat before you say au revoir.

St. Maarten to St. Maarten - 56 Days

Explore the depth and breadth of the Caribbean on this 56-day odyssey, from tiny yachtsmen’s favorites to glitzy celebrity getaways, historic colonial towns to the incredible jungles of wildlife. Go cave tubing in Belize and diving in Bonaire. Snorkel with friendly sea turtles and rays in waters as clear as glass. Climb the battlements of colonial forts and the arrowhead peak of Gros Piton in St. Lucia. It’s the ultimate cruise, circling the Caribbean discovering the brilliant colors, textures and fascinating history found here.

St. Maarten to Bridgetown - 14 Days

Little ports, remote reaches and sincere island pleasures exclusive to small-ship cruising beckon during this two-week exploration of the Caribbean’s Windward and Leeward Islands. Take the wheel of a 4x4 buggy and follow dirt roads along the rural outskirts of Falmouth Harbour on Antigua. Sail from Gustavia to remote Colombier Bay and swim or sunbathe among anchored mega yachts prior to elegant snacks and cocktails. Stroll amid brightly painted shops and beach boutiques along the palm-lined shores of Soper’s Hole in Tortola, or relax and sip sweet, rum-flavored cocktails at a waterfront café. Sit back in airy rattan furniture as you ride a refurbished railcar along a century-old narrow-gauge railway on St. Kitts. Take an ATV tour along deserted roads and abandoned villages near Foxes Bay and hear memories of life before the Montserrat Volcano eruption. Scan the horizon for breaching whales as your catamaran captain and crew sail into former whaling waters off Dominica.

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.

Depart from New York and cruise along the East Coast prior to exploring Bermuda and the Caribbean’s Leeward Islands in detail during this 21-day escape. Snorkel above Bermuda’s most popular shipwrecks—a Confederate paddle wheeler and a four-masted sailing ship—near Hamilton, then dine on juicy swordfish, decadent lobster and seared tuna steaks prior to overnight stays there and in St. George’s. Sail a swift catamaran along the scenic leeward side of St. Barts near Gustavia. Roll past rural cane fields and rustic country farms during a guided ATV outing near Basseterre on St. Kitts. Dance, dine and celebrate at a Windstar Signature Beach Party with friends and crew at Virgin Gorda. Kayak from tangled mangroves to the vast expanse of open blue sea on a guided exploration of Puerto Rico’s Vieques coastline. Soar among colorful rainforest birds and verdant tropical trees during a canopy zipline adventure on Pigeon Island or take a leisurely-paced seaside painting class at St. Lucia’s picturesque Rodney Bay Village.

Start off with a splash in Aruba at some of the Caribbean’s best beaches. Then it’s off to Colombia for romantic Santa Marta’s museums full of pre-Colombian gold and Cartagena’s 400-year-old walls with stories to tell. Relax at sea en route to Bocas del Toro and soak up the laidback atmosphere full of colorful clapboard houses. Hop over to Costa Rica’s Puerto Moin to sample cashews and access amazing national parks. Once in Colón, head to the jungle to meet Embera Indians or take an aerial tram ride through the rainforest canopy.  On Isla San Andres, swim with puffer fish and sea turtles at the UNESCO Biosphere Reserve. Enjoy a day at sea before snorkeling, kayaking or swimming with dolphins in the ocean playground of Roatan and don’t forget to sample baleadas and pastilles with delicious Honduran coffee. In Belize City, visit the howler monkey sanctuary then travel north to Costa Maya to explore the ancient Mayan ruins of Chacchoben. Appreciate the 600-mile-long Mesoamerican reef one more time in Cozumel by adventuring into Chankanaab, an eco-park with underwater caverns home to dolphins, manatees and sea turtles.

Volcanic peaks, remote reefs, verdant rainforests and colorfully painted Caribbean ports abound throughout this remarkable 18-day cruise with stops in the Caribbean, Colombia, Panama and Costa Rica. Dive or snorkel amid schools of bright colored reef fish near small port Bequia on St. Vincent & the Grenadines. Stroll worn, cobbled streets in the historic Punda Quarter of Willemstad and shop for fresh fruit and handmade trinkets at the nearby floating market. Ride a horse-drawn carriage through the narrow lanes streets of Cartagena’s walled Old Town, rolling past regal colonial mansions built when Spanish galleons protected Colombia’s coastline. Experience a fully guided daylight transit of the Panama Canal, and uncover the deadly obstacles faced by French and American engineers prior to its 1914 completion. Trek beneath the shady overgrowth of centuries-old trees while scanning the high canopy for reclusive monkeys, brightly colored tropical birds and slow-moving sloths in Costa Rica’s Manuel Antonio National Park.

From mesmerizing steel-drum bands to unforgettable spicy chicken smoked and grilled in recycled oil drums, this 18-day tropical adventure offers extraordinary experiences in Costa Rica, Panama, Columbia and the Caribbean. Wander among Willemstad’s colorful, gabled store façades and narrow streets. Snorkel or SCUBA amid Bonaire National Park’s dizzying and colorful schools of fish. Sample endless variations of St. Maarten’s mouthwatering marinated ribs. Take in the entire Panama Canal during a narrated daylight transit. Depending on which direction you travel, this exceptional cruise can add a land tour to either conclude or begin your adventure among fragrant rare orchids concealed in the leafy shade of 300-year-old trees in Costa Rica’s Monteverde Cloudforest.

Puerto Caldera to Bridgetown - 28 Days

Lush rainforests, centuries-old colonial fortifications and bright-sand beaches await throughout this extensive 28-day Caribbean exploration that visits ports in Costa Rica, Colombia and both the Windward and Leeward islands. Ride horseback beneath a verdant rainforest canopy or test your fishing skills in a deep sea fishing region known for tuna, sailfish and mahi-mahi off the coast of Costa Rica. Hike among thousand-year-old teak and mahogany trees on Isla Parida in Panama. Experience the energy of the thriving Panama Canal during a complete daylight transit. Explore the reinforced chambers and shadowy stone corridors of the Fort of San Felipe de Barajas near Cartagena in Columbia. See the Aruban countryside and visit prominent landmarks like the Alta Vista Chapel during a guided mountain bike tour. Watch from the railing aboard an authentic Siamese junk as you sail to a remote, uninhabited island and snorkel amid friendly reef fish along Ebo’s Reef outer edge near Kralendijk. And embrace the spirit of small ship ports like Isla Parida, Puerto Jimenez, Quepos, Mayreau, and Deshaies.

Your journey begins in a Bridgetown, a city with Jolly Ole England flavor and two UNESCO sites before an opportunity to swim with sea turtles in Tobago Cays Marine Park. Save your appetite for the exclusive Signature Beach Party on Mayreau and feel the heart and soul of St. Lucia in Soufriere as you wander the vendor-filled streets. Savor a day at sea before bird watching for flamingos and parrots in Bonaire. Delight in the pastel colors of UNESCO site Old Town Willemstad and explore the limestone formations and petroglyphs of Hato Caves. In Aruba, laze on some of the Caribbean’s best beaches or interact with the locals while they play dominos. Romantic Santa Marta boasts coastal mountain beauty and museums full of pre-Colombian gold and jewelry while the 400-year-old walls of Cartagena invite reflections on conquistadors and plundering pirates. Relax at sea en route to the multicultural, multicolored town of Bocas del Toro, Panama where Columbus visited in 1502. Hop over to Costa Rica’s Puerto Moin to access amazing national parks, pristine beaches, and surf. Once in Colón, head to the jungle to meet Embera Indians or take an aerial tram ride through the rainforest canopy.

Bridgetown to Bridgetown - 10 Days

Indulge your senses during a scenic and delicious 10-day Caribbean cruise between the Windward and Leeward islands. Stir up genuine Creole cuisine under the guidance of a local chef and sip fiery rum at a distillery near Anse Mitan on Martinque. Sail on a catamaran and watch for whales or swim with sea turtles in the blue coastal waters off of Guadeloupe. Pedal on a leisurely bike tour of the verdant Rockland Estate Park and meander through a restored colonial plantation near Philipsburg on St. Maarten. Discover Snuba snorkeling near the golden sands of South Friars beach near Basseterre on St. Kitts. Shoot for par amid the manicured tropical ambiance of the Cedar Valley Golf Course near Falmouth Harbour. Take the helm of a 17-foot speed boat and discover views of the Pitons and St. Lucia’s picturesque west coastline prior to mingling among locals in the fishing village of Canaries.

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