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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.

What’s a roti? The simple answer is the ultimate comfort meal of curry wrapped in a thin dough—borrowed from India and perfected in Trinidad and Tobago. You have to understand — making roti is not an easy task. Like many other traditional Caribbean foods, it takes a lot of time and effort to make something this comfortingly delicious… And perhaps those hours of anticipation actually added a little something to the flavors when you finally got the finished, hot roti in between your hands. It starts with the “skin” or roti (officially, only the skin is called roti, but in the Caribbean, we apply the name to the whole package). This is where a roti becomes a success, or literally falls apart. Any time you buy a roti, this is always the thing most people comment on. “Skin’s too thin.” “Skin’s too thick.” “Skin’s too dry.” Etc. The roti skin has to be just right, or the whole thing will fail. My favorite type of skin is dhalpuri which is just what you’ll find at Roti King — now just ask them to fill it with goat, chicken, or shrimp and you in business!

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.

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.

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.

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.

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.

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.

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.

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.

This week on Travel Tales by Afar, writer Santi Elijah Holley shares his 400-mile hitchhiking journey through Oregon—a leap of faith that tested whether a young Black man could find belonging in one of America’s whitest states.

In this week’s episode of Unpacked by AFAR, senior news editor Michelle Baran explores how we can travel safely, smartly, and compassionately in a climate-changing world.