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Sailors place the Grenadines, with its 32 breathtakingly beautiful islands and islets, among the world’s best places for boating. For help getting out on the water, turn to Horizon Yacht Charters, which rents monohulls and catamarans (either bareboat or crewed) out of Blue Lagoon Marina on St. Vincent. Enjoy a multi-day or week-long sail around the Grenadines, or opt for the one-way charter and sail south through the Grenadines all the way to Grenada, where Horizon has another facility.

From this 900-foot-high viewing platform—equipped with a telescope, map, and signage—you have a panoramic view of the majestic Mesopotamia Valley (“Mespo”), home to St. Vincent’s fruit, vegetable, and spice crops. A sea of green expands in every direction, bordered by the blue Caribbean far to the south and the mist-shrouded Grand Bonhomme Mountain to the north. It’s the perfect spot to soak up St. Vincent’s rich natural beauty—and to catch a cool breeze.

One look at this hilltop fort, perched over the Port of Kingstown, and you know the British built it to fight the locals rather than to meet any threats coming by sea—all the cannons face the island’s rugged interior, where the Caribs lived. Inside the fort, you’ll find a series of murals depicting the bloody Carib wars. Kids will love exploring the old buildings, and everyone will enjoy the views.

Between 1812 and 1815, the British ordered the construction of 300-foot-long Jasper Rock Tunnel (more commonly known as Black Point Tunnel) to provide better access from the cane field to the sugar factory to the ships for export. Slaves were responsible for the actual building, manually cutting through the mountain with shovels, picks, and sledgehammers. Now part of the Black Point Historic and Recreation Park, the tunnel also served as the site for several scenes in the first Pirates of the Caribbean movie.

The waters surrounding Bequia beckon scuba divers with everything from brilliant sponges, colorful fish, and deep-water corals to shallow reefs, sheer walls, caverns, holes, and wrecks. While the area is home to 30 or so easily accessible diving sites, you should head to the designated marine park, which occupies seven miles along Bequia’s leeward coast. Family-run outfitter Dive Bequia (located on Belmont Walkway in Port Elizabeth) offers three dive trips to the park each day, along with instruction, certification, and rental gear. Divers must be at least 8 years old, but snorkelers of all ages are welcome as well.

Three blocks inland from the waterfront, on Frenches St., the Craftmen’s Centre sells locally made, reasonably priced crafts: intricate grass mats in sizes ranging from place mats to full floor mats, colorful batik cloth, handmade West Indian dolls, hand-painted calabashes, and more. Cash only! (P.S. The grass mats roll or fold into a neat bundle to carry home.)

Whether you come for a drink, an appetizer, or a full meal at Flow Wine Bar and Kitchen in downtown Kingstown, you won’t be disappointed. The atmosphere is cool, with flickering candles and soft music, and the kitchen serves a wide range of small plates, entrees, flatbreads, sandwiches, and pastas, all perfect for pairing with the extensive wine selection. When you’re finished here, try sister spots Flowt Beach Bar at the Blue Lagoon Hotel & Marina (for cocktails and grilled fare), or Bungalow on the Villa Beach boardwalk (for pizza).

Locals consider La Soufrière—St. Vincent’s massive active volcano that last erupted in 1979—the “queen of climbs.” Approachable from either the leeward or windward coast, the hike to the 4,000-foot summit is a serious, all-day excursion. You’ll need stamina and sturdy shoes—and a knowledgeable guide from the National Parks Authority—to safely reach the top, but once there you’ll enjoy breathtaking views of the surrounding landscape and sea. Keep your eyes peeled for a rare sighting of the St. Vincent parrot on the way back down.

If you were to picture the perfect Caribbean beach, it would probably look something like Salt Whistle Bay on Mayreau. Here, clear, turquoise waters lap at 2.5 miles of sparkling white sand, while palm trees, seagrape plants, and flowering bushes provide shady spots for lounging. At one end, you can walk the few yards of land that separate the Caribbean and Atlantic sides of the island. The only catch is that you’ll need a boat to reach the beach, so rent your own or book a day sail to Mayreau.

Among several sea and land excursions, locally owned Fantasea Tours offers full-day whale- and dolphin-watching trips along St. Vincent’s leeward coast. You can expect to see pilot whales, orcas, and several species of dolphins year-round, but the best time to spot them is December through April. Huge sperm whales and humpbacks stop by seasonally, usually from October through January. Regardless of when you go, you can look forward to an exciting, comfortable tour. Fantasea’s staff is extremely knowledgeable, and its boats and equipment meet the highest safety standards.

In the Caribbean’s Windward Islands, a string of some 600 islands and islets dot the sea between St. Lucia and Grenada. It’s a paradise for yachters, where you can drop anchor off an uninhabited island and live out your Robinson Crusoe fantasies. A handful of these islands are home to resorts, including the private Palm Island, first leased to an American couple in 1966 for $1 per year. They established the ten-room Palm Island Beach Club, which over the years has grown—though there are still only a total of 43 guest rooms on this single-resort island.

For an introduction to the Rastafarian culture and lifestyle, head to OJ’s Ital Cart in Basseterre. The brightly painted food truck takes a pure approach to its menu, offering vegetarian fare that’s fresh, natural, and from the earth. Ingredients are grown without chemical pesticides or fertilizers, and even the salt used to flavor dishes is iodine-free. While lines often wrap around the block at lunchtime, the vibe is always fast and fun. When you’re seeking something healthy, join the crowds for pastas, sautéed soya, fresh local juices, and more.

An archipelago within an archipelago is already an astonishing fact to grasp, but Îles des Saintes, made up of nine islets, only two of them inhabited, is full of yet more surprises. Hop on a daily ferry ride south from Trois-Rivieres in Basse-Terre to these gorgeous offshore islands around a stunning aquamarine bay dotted with sailboats and hugged by coral reefs. Also known as Les Saintes, these islands combine a traditional Caribbean setting of secluded beaches, forts, and towering palm trees with a chic French village lifestyle. The streets here are free of cars, the winding roads to be explored by electric scooter or on foot. Hike to Fort Napoleon for a breathtaking panoramic view over Les Saintes Bay, explore the surrounding waters by catamaran, go diving off the bluffs, sample some of Guadeloupe’s best French and Creole fusion restaurants, and shop the boutiques for French fashions and local jewelry.

Dating to 1521, the Cathedral of San Juan Bautista isn’t just one of the oldest buildings in San Juan—it’s the second-oldest cathedral in all of the Americas. Go inside to see the tomb of Spanish explorer Ponce de León, who founded the first settlement on Puerto Rico and in 1509 was named the island’s first governor. The remains of St. Pio, a Roman martyr, can also be seen in the cathedral—the saint’s mummy has been displayed here in a glass box since 1862.

Scattered with Victorian mansions, St. Paul’s tree-lined Summit Ave. is one of the most beautiful residential streets in the Midwest, with famous former residents including author F. Scott Fitzgerald and early railroad entrepreneur James J. Hill. Guided tours are offered from the James J. Hill House Wed–Sun, but it is also a worthwhile independent stroll. Make sure to start or end at the gorgeous St. Paul Cathedral, overlooking downtown St. Paul.