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The Yannis catamaran departs from Palm Island Resort (but will pick up passengers at nearby Union Island as well) for a full day of sailing, swimming, and snorkeling at the beautiful Tobago Cays and Mayreau’s magnificent Salt Whistle Bay Beach. A buffet lunch, beverages, and snorkeling gear are all included, making this one of the easiest ways to see some of the most breathtaking locations in the Grenadines.

A 100-foot schooner based in Bequia, The Friendship Rose takes passengers on daylong cruises to Tobago Cays for snorkeling and swimming with sea turtles, or Mustique for beaching, bar hopping, and relaxing. Excursions include breakfast, lunch, afternoon tea, and drinks throughout the day, including beer, fruit punch, and soft drinks. Whether you opt for the marine park or the private island, the entire family is sure to enjoy the experience.

Store Bay, just outside Scarborough, is one of Tobago’s most popular beaches. Reserve some time after your swim for a visit to the dozens of bright and cheery craft shops and food stalls that make up the Store Bay Beach Facility. Need souvenirs? Browse for island crafts like batik, sandals, jewelry and items carved from wood and coconut shells.

Just to the north of Galley Bay Resort, you’ll find one of my favorite beaches on the island and maybe even the entire Caribbean: Deep Bay. The ruins of Fort Barrington keep watch over this incredible, crescent-shaped slice of paradise, just adding to the beauty of its turquoise, flat waters. Swimming here is like splashing in the largest, most pristine, natural pool you’ve ever imagined. As an added bonus, there’s a hundred-year-old sunken wreck, a barque from Trinidad named the Andes, out in the middle of the bay. It’s an easy swim from shore and accessible to snorkelers. Beaches really don’t get much better than this... anywhere.

A long jetty with a thatch-roofed shelter at the far end is the signature motif of Pigeon Point Heritage Park. This is Tobago’s favorite swimming beach, a classic scene of golden sands bordered by coconut palms. The well-maintained 125-acre park is also a hub year round for island events, from dragon-boat races and culinary feasts to jazz and other music festivals. Colorful glass-bottomed boats pick up visitors here for tours over the ample reef system. And there’s shopping, too: Look for island-made ceramics, batik and beachwear.

In the 1770s, at a time when islands were changing hands dozens of times, both the French and the British gave Tobago something every island needed—forts overlooking bays. Today, the cannons at Fort King George, constructed by the English, still point out to sea. Visitors enjoy the site, high on a hill over Scarborough, for its marvelous views. The restored stone structure that was once a barracks now houses the Tobago Museum, with exhibits of military relics, maps and pre-Columbian artifacts.

For a break from Port-of-Spain’s congestion, a 15-minute drive up curvy roads outside the city leads to Mount St. Benedict Monastery, with its fine hilltop views over the plains, the coast and the Northern Range. Just over a century old, the enormous yellow monastery (also known as The Abbey of Our Lady of Exile) sits on a large swath of land whose hikeable woods are filled with birds. The monks sell their popular homemade yogurt while the guesthouse serves traditional afternoon tea.

Maracas Bay is known as much for “bake ‘n’ shark” as for its fine waves. Hungry beachgoers line up at shacks to devour deep-fried fish (rarely shark) that is packed into fried dough sandwiches and served with a plethora of spices and pepper, tamarind, garlic and oyster sauce.

Named for the beach it sits on and famous for its views, Moonstone Grill is set at the junction of Little River and the Pacific, with a patio and large windows overlooking both. Given its full bar and specialty cocktails, many visitors like simply to enjoy a drink and take in the sunset. That’s a shame, because the food is good, too. The menu consists of local appetizers, seasonal seafood plates, and top-notch steaks. It’s not cheap, and you’ll want to make a reservation: Word has gotten out about this high-end, low-key Humboldt classic.

Just seven hectares (17 acres) in size, the Botanical Gardens in Scarborough pack a tropical punch. They were founded in the 19th century on a former sugar plantation, with views of the town and bay. Visitors will see orchids and bromeliads, royal poinciana and silk-cotton trees, a huge saman tree with spreading branches and an allée of stately palms. Keep an eye out for the island’s colorful blue-crowned motmot bird flitting about the grounds.

For more than two decades, Tobago’s own Ted Arthur has been turning out his own line of high-quality leather goods and accessories—sandals, satchels, handbags and jewelry. His work is influenced by the tropics, and often adorned with palm trees, leaves and hibiscus flowers. Past customers have included the Obamas and Richard Branson as well as musical celebrities Chaka Khan and India Arie. Visit his shop on Scarborough’s Milford Road Esplanade to pick up a finely crafted memento of Tobago.

If the romance of a vineyard sounds appealing, several wineries offer you the chance to dine among the vines. Locals choose the Vega Manchón Winery (pictured here), where former Rosewood chef Carlos Segura pairs entrées with the vineyard’s wines. Restaurante de la Santísima Trinidad, nestled within the grounds of its namesake vineyard, is open only on weekends but can provide a relaxing daylong respite, especially if combined with the winery’s other diversions like polo matches (and polo lessons for all levels of expertise), yoga, or massages. For best romantic results, follow the recipe of poet Omar Khayyam, “A jug of wine, a loaf of bread, and thou….”

Wine aficionados set their sights on the Guanajuato Wine Route, now perhaps second only in Mexico to the trails in Baja California’s long-established Valle de Guadalupe. While wineries have existed in this region for several decades, San Miguel only recently received official designation as a wine route, thanks to wineries like Vega Manchón (owner Ricardo hails from Mexico City); Bodega Dos Búhos, where art by Peter Leventhal mesmerizes visitors almost as much as the wine; or Vinícola Toyán. Newcomer labels like Santísima Trinidad have joined the old-timers in hosting vendimia events every weekend in August, with Santísima adding extra attractions like polo games and olive-oil demonstrations. No going Sideways for oenophiles here; they will head home with a new wine destination secret—and a bottle or two.

The canal’s descent back to sea level begins at the Pedro Miguel Lock, whose single step is almost quaint in comparison what’s happening in the canal’s other two sets of locks. Yet, so vitally important is it that Presidents Theodore Roosevelt and William H. Taft both stopped to inspect excavations and address workers here. The lock is so narrow that you could almost reach out and touch the “mules,” the toylike silver locomotives that guide the ships.

Mandarin Oriental’s first Caribbean resort has all the amenities you’d expect from the luxury brand—with the price tag to match. Nestled within lush greenery overlooking the white sands of Godahl Beach, the 26 suites and villas, which sit on the grounds of a 1,200-acre estate on the island of Canouan, are elegantly appointed with modern furnishings, marble baths, and rosy accents befitting the hotel’s name. Here, though, it’s all about the public spaces, including a Jim Fazio–designed golf course overlooking sparkling blue waters, a hilltop spa specializing in island-themed treatments, and four elegant restaurants serving every kind of cuisine, from pan-Asian to Italian. At Turtles, a cocktail lounge straight out of the Hamptons, opt for the Pepper Bliss, made with rum, bell pepper syrup, and pineapple juice.