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Classic Caribbean

Rates & Dates:

Trip Length: 8 Days/ 7 Nights

Prices from: $4,999 pp/do*

Ships: Wind Surf

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ClassicCarib

Discover Windstar’s landmark Caribbean cruise. In this single experience you’ll find the flavors, cultures, and colors of the Caribbean’s distinct and diverse heritage combine to delight all your senses. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivreunique to the Caribbean life. It’s a yachting delight – and our foremost Caribbean voyage. Even better, the world’s most amazing water park is as close as the aft of your yacht. Our private Watersports Platform transforms Wind Surf into an aquamarine playground – with everything you need for tropical water fun ready and waiting for you.

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Day 1: Philipsburg, St. Maarten: It’s been some 300 years since the Dutch and French established a truce on tiny St. Maarten, dividing the island into two delightfully distinct yet amicable parts. So amicable, in fact, that you can cross back and forth freely from one side to the other. Philipsburg is the vivacious capital of the Dutch half. Along Front Street, the citrus-colored buildings are home to gourmet restaurants, lively casinos and some of the best duty-free shopping in the world. Pause for a taste of the local guavaberry rum, listen to street musicians play on the broad boardwalk or head to the French-side village of Grand Case for conch fritters and quaint Creole architecture.

Day 2: Barbuda, Barbuda: This picturesque island is what most cruisers are looking for but won’t find, because most cruise ships don’t stop here. (They can’t.) Life here is sleepy, laid-back, unspoiled — pick your adjective. There are a few ruins from plantation days, but mostly the entertainment is of the do-it-yourself variety: watching plumes of white spray splash up from the reef, collecting conch shells, or if you’re feeling ambitious, a trip to the Frigate Bird Sanctuary to watch the giant-winged avians harass other seabirds for their catches like the man o’ wars they’re nicknamed for. The only thing that can be really called grand (aside from the island’s beauty) is the 20-mile stretch of pink sand beach that greets us when we arrive.

Day 3: Roseau, Dominica: Dominica’s unspoiled, Eden-like environs haven’t gone unnoticed by Hollywood, and it’s performed admirably as the setting for more than one famous pirate movie . The real treasure here, though, is nature itself. While it’s one of the largest islands in the Caribbean, “The Nature Island” has one of the smallest populations, but an abundance of rivers, waterfalls, hot springs, mountains, and black and white sand beaches. Plus, nearly 300 miles of hiking trails to explore it all. The parade of flora and fauna might begin before we even reach port, since Dominica is also known as the Whale Watching Capital of the Caribbean. Compact Roseau, the capital, has escaped the development found on other Caribbean islands. Its streets brim with tidy Victorian homes and bustling markets, with nary a big-box store or hotel chain in sight.

Day 4: Pigeon Island, St. Lucia: The dramatic approach to St. Lucia, with its iconic twin Pitons rising from the sea, hints at the wonders ahead. The rain forest is home to giant primeval ferns, wild orchids, and birds of paradise, while flamboyantly colored birds like the indigenous St. Lucia parrot fly overhead. Along the coast, you’ll find the remains of old fortresses, warm and welcoming villages, and open-air markets brimming with locally made batik fabrics and woven hats. Offshore is a treasure trove of pristine coral reefs, peacock fish, parrotfish, and other species. We’ll dock at Rodney Bay Village rather than the more developed cruise ship port of Castries, giving you the choice of whether to head for civilization or focus on a blissful escape from it.

Day 5: Les Saintes, F.W.I.: There are only two inhabited islands in this tiny archipelago south of Guadeloupe, and they’re yours to explore as we anchor just off Terre-de-Haut in one of the most beautiful bays in the world. (Larger ships dock at Pointe-a-Pitre, Guadeloupe’s main city, and must take a ferry to Les Saintes.) It’s impossible to get lost in Terre-de-Haut, which has only one street, but there are still plenty of ways to spend your day in this vintage bit of the old Caribbean. Pick up some fresh and fragrant baguettes for a picnic on the beach. Visit with the fair-skinned Saintoise, said to have descended from Breton corsairs (pirates) and known for their skill at fishing and sailing. Climb to Fort Napoleon for incredible harbor views and a look at the exotic gardens in the fort’s former ramparts.

Day 6: Basseterre, St. Kitts: St. Kitts was once the richest British colony in the Caribbean thanks to the world’s appetite for sugar. The industry finally shut down in 2005, but the island is still a sweet place to spend time with its Victorian gingerbread architecture and intriguing mix of history and natural splendor. More than a quarter of the land is designated as a National Park, complete with rainforest and a smoldering volcano, but it’s Brimstone Hill Fortress that sets the island apart from other former colonies. It was called the Gibraltar of the West Indies for its ability to withstand 18th-century attacks, and even comes with its own brand of ape–the pet green vervet monkeys released by the French when the British gained control.

Day 6: Charlestown, Nevis: This 36-square-mile island lies near the top of the Lesser Antilles archipelago, about 200 miles south of Puerto Rico, and just west of Antigua. This island jewel is approximately 7 miles long and 5 miles wide, with natural vegetation that is unparalleled. Green and serene, Nevis is truly one of the remaining unspoiled places and proudly carries the name, “Queen of the Caribees.” From the top of the 3,232-foot Nevis Peak to the depths of the clear waters offshore, there is a world of flora and fauna to be explored. In the hills, the comical green vervet monkeys chatter and scamper; in the sea, the whales cruise by. Stroll around and see the architecture of eras gone by: churches, windmills, and refurbished Great Houses. Its 10,000 residents are friendly and helpful, ready to make new friends and welcome back regular visitors. The genuine charm and hospitality radiate into the unspoken: “Welcome, Be my guest, and Do come again.”

Day 7: Gustavia, St. Barthelemy: When the rich and famous head to the Caribbean, like as not they head to St. Barts. Not a bad outcome for an island the French originally sold off as being too hilly, rocky, small, and dry to be profitable. Others did see potential here though—first French buccaneers and later Sweden, which turned it into a profitable free port during the colonial wars of the 18th century. France eventually bought the island back, but the free port status remains, making this a great place to shop for everything from the latest French fashions to island crafts. Have lunch at the infamous “Cheeseburger in Paradise” made famous by Jimmy Buffet. Watch for celebrities along the Rue de la République. Stand at the rail as we depart under the stars by sail power alone, without even starting the engines.

Day 8: Philipsburg, St. Maarten: It’s been some 300 years since the Dutch and French established a truce on tiny St. Maarten, dividing the island into two delightfully distinct yet amicable parts. So amicable, in fact, that you can cross back and forth freely from one side to the other. Philipsburg is the vivacious capital of the Dutch half. Along Front Street, the citrus-colored buildings are home to gourmet restaurants, lively casinos and some of the best duty-free shopping in the world. Pause for a taste of the local guavaberry rum, listen to street musicians play on the broad boardwalk or head to the French-side village of Grand Case for conch fritters and quaint Creole architecture.

Photo Credit: Windstar Cruises