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Rurutu, located in the remote Austral Archipelago, is a magical land of migrating whales, abundant vegetation, limestone caves, and smiling faces. Accessed via Air Tahiti flights from Papeete five times per week, the car-free island is like no place else in French Polynesia. Comprised of a massive chunk of coral that was lifted up to form it, Rurutu has otherworldly topography – think sheer cliffs of pocked coral and giant caverns filled with ferns and stalactites. It is home to unique coral snorkeling, white-sand beaches, sacred marae, and fabulous biking (the island is very hilly). A continuous reef rings Rurutu (so there’s no lagoon), but despite the open ocean fronting it there are more beaches on Rurutu than most French Polynesia islands. The sand is also a bright white here and made from ground, bleached coral. Besides lounging on the beach, you can look for whales along the shores from roadside observation stations between July and October. Note, unlike the rest of French Polynesia, the Australs get really chilly between May and November and are best avoided during this time. From December to April you’ll find warmer temps, but it still isn’t hot enough for air-conditioning most of the year.

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.

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.

Among vacationers who’ve been coming to Grand Cayman forever, there’s a whole faction that essentially camps out at Rum Point all day every day, and you’ll understand why as soon as you see the place. Tucked away, super low-key, and graced with a ridiculously photogenic pier—its perfectly weathered planks cutting a striking figure against the tranquil, turquoise surroundings—this beach is the ultimate spot for settling into a lounger or hammock between water-sports outings. Rum Point’s namesake booze—which used to wash ashore by the barrel, according to legend—is available in all manner of cocktails here, of course. But order at least one mudslide at its spiritual birthplace: the beach’s beloved Wreck Bar.

Living in Hawaii, I find it’s not hard to appreciate macadamia nuts. After moving to the Islands, I did not waste any time determining my favorite kind of chocolate-covered mac, Mauna Loa. As with many other companies, mac nut orchards dot the Big Island, which has a great growing environment for the unusual nuts. The Mauna Loa Macadamia Nut Company operates a visitors’ center on the Big Island along with their orchards and processing plant. A tour of the area includes a farm to final product education and, of course, free samples for your enjoyment. I always keep several boxes on hand to give to my house guests to welcome them to Hawaii, but mac nuts are also a great gift for tourists to bring back home.

From the first time I set foot on the island of Ambergris Caye, Caramba became my favorite restaurant in San Pedro. And that’s not changed, even ten years later. Rene Reyes, Sr. and his wife Patty have done a remarkable job with the restaurant. Every season brings something new and exciting – whether it be décor changes, menu enhancements or even new cocktail creations. The Reyes’ sons Jonathan and Renesito are now involved in day-to-day operations, keeping Caramba one of the long-standing family-owned and operated businesses on the island. Personal recommendations include Conch Fritters (seasonal), Sopa de Lima, Fish Tacos, Pibil Pork Sub and the Coconut Shrimp. Any of the seafood dishes are spectacular – go for the Maya or Tour Guide cooking options. Be sure to try one of bartender Charlie’s cocktails, like the Strawberry Beerita, King Margarita, or a special mojito. Not a drinker? Caramba has some of the best fruit smoothies on the island. Closed Wednesdays. Check Foursquare for current specials.

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.

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.

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.

For many travelers to Greece, there’s a conundrum: Do you concentrate on the mainland—Athens, Delphi—or do you spend your time cruising the islands—from fashionable Mykonos to holy Patmos? With Grand Circle Cruise Line, you don’t have to make that decision. The first week of the 15-day Treasures of the Aegean: Greek Island Cruise, Athens & Istanbul itinerary includes the monasteries of Meteora, perched atop rock formations; the town of Kalambaka, Thessaly, where you’ll discover a Byzantine tradition when you stop at an icon-painting workshop and meet one of the artisans; and the majestic ancient sanctuary of Delphi. Then you depart on a cruise to the Aegean’s most beautiful islands aboard a 50-passenger small ship. You’ll call at ports including Amorgos, Delos, and Naxos, where you’ll sit down for an island dinner with some of its residents. While you’ll be following the routes of ancient heroes, Grand Circle assures that travelers also experience modern-day life in the country from those who live, work, and play here. Exclusive Discovery Series events take you deeper, show you more, and give you an unfiltered look into daily life whether you’re dining with a Greek family during a Home-Hosted Dinner, or participating in a cooking class in the mountain village of Arachova.

For those who aspire to travel as trendsetters in Jamaica, it helps to know that Port Antonio, way out on the eastern end of the island, is the destination to head for. And the address to shelter at is the Trident Hotel, whose 13 waterfront villas would not look out of place on South Beach. Nor would the crowd that hangs around its infinity pool or in its restaurant, Mike’s Supper Club, where local musicians and the occasional celeb sit down to knock out tunes on the 1917 Ferrari-red grand piano. The Trident Castle, a kind of fantasy annex, is a former private residence whose grand rooms, sea-view terraces, and dollhouse-size chapel make it ideal for destination weddings. A hard road to get there? Not for guests who avail themselves of the helicopter pad.

If you’re looking for tropical tranquillity, bypass Maui’s buzzy resort enclaves and head away from the coast to the island’s laid-back Upcountry, where you’ll find Lumeria. At the 24-room wellness retreat, visitors can start the day with a guided sunrise meditation, then strengthen their yoga practice, learn to hula or surf, and go snorkeling off the North Shore. Spa treatments include Hawaiian massage and acupuncture as well as nontraditional therapies like crystal healing and shaman-led journeys. The schedule is flexible, so you’ll have plenty of time to learn about Hawaii’s paniolo (cowboy) culture or just take in the ocean views from your private lanai. Guest rooms feature art by local Maui artists, four-poster beds topped with organic linens, and stone-tile showers stocked with Aveda products, while the Wooden Crate restaurant prepares farm-to-table meals with nearly 200 types of fruits and vegetables that grow on the property.