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Situated off the eastern shore of Long Island, The Chequit is old school in an elegant way. The hotel occupies a big white building, surrounded by grassy lawns, impeccably maintained hedgerows, and towering deciduous trees, and features bright, homey rooms, complete with large windows that let in plenty of natural light. While all the rooms have been refurbished, those in the main house retain much of their original architecture, lending them a certain vintage charm. The Chequit operates on a bed-and-breakfast model, and guests can either take their morning meal in the lobby or opt to have a lighter option sent straight to their room. While the target audience here is weekenders seeking an escape from New York City, the hotel is also a popular spot for weddings and retreats, with two meeting rooms and full catering services available from on-site Red Maple Restaurant.

Lefkada is the only Greek island accessible by land, but it doesn’t mean it sees a lot of tourism. On the other hand, it’s hard to believe it ISN’T one of the most highly sought after destinations: Egremni Beach is one of the best beaches in Europe, and the island is home to important sights like the Nydri medieval castle of Agia Mavra. Lefkada is also famous for its kitesurfing community. If you’re a kitesurfer, you’ll want to check it out. And if you’re not, maybe it’s time to try something new?

Backed by the green of mountains flecked by red rooftops, Lorient Beach is an unspoiled stretch of white sand and beautiful blue water. Favored by locals, fishermen, and visitors, this north coast beach has excellent surfing at one end and calm water for swimming, snorkeling, and stand-up paddle boarding at the other end. The nearby village of Lorient, the site of the island’s first French settlement, is rich in culture. Here visitors are drawn to the 19th century Catholic church, historic bell tower, and Ligne Saint Barth—a famous luxury soap, shampoo, and perfume manufacturer.

In swank St. Barth’s, it’s hard to imagine that it’s only the Gucci-clad glitterati that live here. In an effort to see for myself, I rented a jeep and on a quiet Sunday morning drove around the island. I stopped at L’Orient Beach where my question was answered. Families played in the turquoise sea, suntanned, surfed, ate sandwiches while leaning against the colorful surf shack. It was the antithesis of the rosé-fueled scene at Nikki Beach on the other side of the island. I sat and watched for an hour, trying to take photos, but slipped away, feeling very much the interloper.

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.

Within the St. Vincent Botanical Gardens in Kingstown, visitors will find a very nice gift shop, featuring everything from local artwork, handmade pottery, and crafts to books about the island, toys for kids, authentic souvenirs, and snacks and cold drinks. The gift shop is decorated with plants, of course, as well as carnival costumes that reflect the island culture.

You’ll be hard pressed to find anything other than postcard-perfect scenery in the Exumas, and if you’re ambitious and up early enough, there’s a good chance that you can have Horseshoe Bay in Saddle Cay all to yourself for a few hours. A trip to a private Bahamian island isn’t out of reach for the intrepid traveler, as plenty of outfitters offer affordable tours, overnight adventures, and sightseeing cruises to these gorgeous islands.

Stillwater is a longtime favorite in Launceston for its location on the Tamar River in a lovingly restored 1830s flour mill. Original beams, polished timber floors, and water views set the scene for seasonal dishes such as whiskey-cured Huon salmon; slow-roasted Flinders Island rack of lamb (flavored like ocean salt from the sea-swept grasses the lamb eat); and Cape Grim steak (which hails from the capital of clean air). The same owners run Black Cow Bistro a few blocks up the road, which is doing more incredible things with Cape Grim cuts. Save room for the sweet basil panna cotta with strawberries and breadcrumbs. You can hike it off at Cradle Mountain tomorrow.

Kona coffee is famous around the world as one of Hawaii’s best known products. The relatively small coffee growing area on the Big Island of Hawaii produces only a small fraction of the world’s coffee beans. The limited production makes Hawaii Island’s caffeinated product like liquid gold for Kona coffee lovers. Among the hundreds of coffee farms on the Big Island, Country Samurai Coffee Company operates a lush and green outfit on the Kona slopes and still grows their coffee trees in a natural and traditional method that enables them to grow tall—up to 18 feet. Harvesting requires ladders and can be time-consuming, but the trees are able to develop a larger root system, pull in more nutrients from the volcanic soil, and produce more coffee berries. To try these distinctly grown beans, visit the family owned Country Samurai Coffee shop in Kailua-Kona. The shop sells several other items including chocolate covered coffee beans and macadamia nuts and Hawaiian teas.

On the main road through Grace Bay, this is where locals and return visitors go for the best fresh sushi in town. And while it does amazing sushi and sashimi, including some innovative rolls all ordered off iPad menus, I was really impressed with the seafood ramen noodle soup bowl. The environs are sophisticated and noise level not too loud. A great romantic dinner choice.

There are many reasons to stay at Stargazer, but my personal favorite is the great snorkeling located less than a five minute swim from this gated property’s deserted half-mile stretch of sugar sand and fossil covered beach. The lights of Grace Bay Beach, just a 10-minute drive from this six-bedroom villa, provide a twinkling backdrop when floating in the trio of infinity pools at night. But Stargazer feels wonderfully remote thanks to its secluded residential locale, and privacy of 2.4 gated acres of colorful gardens and indigenous trees. The six bedrooms are located in three buildings, including the impressive 15,000-square-foot main house set up for entertaining.

There may not be much to this tiny island in the French Polynesia but it’s big on history if you have any interest in Paul Gauguin and Jacques Brel. If you are looking for a secluded spot with little amenities, this is a perfect spot in paradise.

The first luxury lodge to come to Chile’s second biggest island, Tierra Chiloé opened in 2012 and became a member of the Tierra hotel group in 2014. Designed by Chilean architect Patricio Browne, the hotel looks like a boat on stilts and was inspired by the homes of local fishermen, which take the same form and are known as palafitos. The exterior is made from picturesque larch wood shingles—a building technique that’s very typical on Chiloé and is seen on the famous UNESCO World Heritage churches that dot the islands.

Inside, guests find more wood. The hotel’s wood walls and ceilings are made from indigenous species . The decorations are locally inspired with plenty of handicrafts such as wicker baskets, handwoven rugs, and wooden carvings. The focal point is the meadow and Reloncaví Sound below, where the hotel’s boat is harbored. Large windows line the building on both floors and provide excellent views. Guests can relax in a small spa, a winetasting room, or a book-filled upstairs studio upstairs. The living room with fireplace makes a perfect spot for an end-of-day pisco sour.

Esperanza is located on the southern side of Vieques island with a laid-back vibe reminiscent of Key West. This small town has an main street that runs parallel to the ocean called “El Malecón” that is dotted with friendly guest houses, funky bars and even gourmet restaurants. It makes a great base for exploring the island’s treasures: it’s walking distance to Playa Esperanza and Sun Bay and only a 10-20 minute drive to the secluded beaches in the wildlife refuge.

Hit Seven Mile Beach, a beautiful and—as the name would suggest—long stretch of shoreline to see why it’s one of the Cayman Islands’ most fabled features. Facing out to sea, you’d be forgiven for thinking you were beholding a life-size Rothko installation, with bands of the palest aqua, the richest cobalt and every gradation of blue-green in between. Also keep an eye out for the schools of fish that sprint along the water parallel to the shore.