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 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
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.
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. George's in Grenada. Your adventure concludes in Bridgetown, Barbados, where you can reflect upon memories and deeper thoughts in the quiet shadows of 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 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.
Colón to St. Maarten - 11 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.
Lisbon to St. Maarten - 19 Days
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.
Bridgetown to Bridgetown - 14 Days
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 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.
San Juan to Athens - 52 Days
Venture from Caribbean beaches, spicy jerk chicken, and rum cocktails to Riviera shoreline fortresses, Moroccan cumin-infused lamb, and robust Italian Sicilian red wines during this epic 52-day cruise that explores the West Indies before crossing the Atlantic to the Azores, Portugal, Spain, Morocco, France, Monaco, Italy, Malta, and Greece. Snorkel among picturesque reefs and vibrant tropical fish in the hidden island gems of the Caribbean including Guadeloupe and the British Virgin Islands, then relax and rest up with multiple spa visits and intriguing lecturers as you sail from San Juan, Puerto Rico to the tropical small port of Horta in the Azores Islands. Taste the important differences among Spanish sherries and fine wines at Cádiz wineries. Browse for trinkets and inhale the aromas of countless spices in a Moroccan market in Tangier. Test your luck at tables inside an opulent casino in Monte Carlo. Wander the ruins of the Roman Forum and the monuments inside the Vatican City in Rome. This exceptional and memorable journey embraces Greek island hopping and concludes in Piraeus, with the storied Acropolis and the Greek Parthenon temple high above Athens.
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.
Colón to Lisbon - 26 Days
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.
Colón to St. Maarten - 19 Days
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 - 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.
San Juan to Lisbon - 20 Days
Combine Caribbean cocktails, steel drum rhythms, and white sandy beaches with Portuguese port wines, fado folk songs and lofty Baroque architecture during this 21-day transatlantic cruise from Puerto Rico to Portugal. Begin with an unforgettable circuit of Caribbean destinations, including Les Saintes, Bequia, and St. Georges, before embarking from San Juan, Puerto Rico and crossing the Atlantic to the Azores and Portugal. Shop among stylish boutiques in Philipsburg, St. Maarten. Dive or snorkel among turtles and vibrant tropical fish off Bequia’s tropical coastlines. You’ll circle back to Old San Juan before relaxing spa days, delicious meals and shared moments throughout a transatlantic crossing to the Azores. Explore Horta’s Old World architecture or Capelinhos’ volcanic slopes. This memorable crossing concludes in Lisbon, the Portuguese capital, where you can dine on Caldeirada, grilled sardines, stuffed crab, and other amazing seafood meals accompanied by the strumming and singing of talented fado performers.
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.
Cozumel to St. Maarten - 18 Days
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 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.
Oranjestad to Cozumel - 17 Days
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.
Puerto Caldera to St. Maarten - 18 Days
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.
Bridgetown to Colón - 16 Days
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.