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Casa Morada’s dressed-down modern coastal style reflects a love of the ocean, island plant life, and luxurious comforts. The 16-suite boutique hotel—once a 1950s roadside motel—underwent an extensive renovation in the early 2000s that transformed it into one of the Key’s sexiest spots. The Raymond Jungles–designed gardens are lush, the outdoors showers and jacuzzis are impossibly romantic, and the resort’s private island features a freshwater pool. If you can rouse yourself for anything other than relaxing by the water, try your hand at a game of bocce, snorkle around the only living coral reef in North America, go on a sunset sail, or charter a boat tour with local resident Captain Bill to visit the Mangrove Islands or Three Sisters Bird Rookery. Pro Tip: Morning yoga classes are offered every Wednesday, Saturday, and Sunday at 9, but guests can book a private session anytime.

The Southernmost Point buoy, at the corner of Whitehead Street and South Street, marks not only the spot for the southernmost point of the continental United States but also the distance (90 miles) to the next country, Cuba. The buoy, installed by the city in 1983, is visited by thousands of people each day. (Before the buoy, a small sign stood at the spot alongside a line of seashells for purchase.) Taking a photo in front of the buoy is imperative for a first visit to Key West, so bring a tripod, or ask a stranger to snap a few shots. Buskers play music, and street vendors sell food and goofy souvenirs and slash open coconuts to drink.

Coney Island’s history dates back to the 1800’s, when it was envisioned as a working man’s paradise. For pocket change, you could enjoy rides and hot dogs. While you’ll need a little more than pocket change now, this venture outside Manhattan has a true charm, and can connect with most anyone’s inner child. Over the summer you’ll find packed beaches, Friday night fireworks, and the famous Nathan’s hot dog eating contest on July 4. But if you’re coming from Midtown or the Upper East/West Sides, be sure to take an express train or you’ll be in for a ride not quite as amusing as the Cyclone.

The government said the cliffs of Calcata, a medieval hill town 30 miles north of Rome, where crumbling and the residents would have to abandon the village for a new one a half mile away. They were right. Sort of. There was a government policy, created during the Fascist era, that stated any village that was so decrepit it was dangerous, the government would destroy it and build a new town nearby. The residents of this cramped hill town, tired of the poor living conditions, took advantage of this law. By the 1960s, the new town, Calcata Nuova, was ready and the old residents slowly moved. At the same time, hippies and artists discovered this slowly abandoned village and bought up the houses, knowing the village was to be condemned. They eventually had the law reversed, saving the village, and went on to fix up Calcata. Today home prices have soared and it’s become one of the most beautiful (and bizarre) places in Italy.

Wymara Resort Turks & Caicos (formerly the Gansevoort aims to be as much a scene as it is a hotel. Of course, with tots wandering through the lobby with sand buckets, it isn’t quite the party you might have in South Beach or NYC. But then, trendy urbanites don’t have this—the white-sand beach of Grace Bay, or an infinity pool with wood-deck islands that can be reserved for sunbathing, private dining, or just making everyone else feel less important. The 91 rooms are designer chic, with an open floor plan and plenty of space to stretch out. Also available for booking are seven luxury oceanfront villas, located on an elevated hillside overlooking the bay and Turtle Tail. Each features four to five bedrooms as well as two private pools, expansive indoor-outdoor living areas, sunken outdoor lounge areas with firepits, and over-the-water swimming platforms with direct ocean access. Stelle, the Mediterranean-influenced restaurant, has a DJ who spins on Friday nights. And Exhale Spa counterbalances the chill party vibe with sunset yoga in an outdoor pavilion.

The moment you walk into Buba’s, you feel like family. It’s easy to understand why when you consider that surrounding this blink-and-you’ll-miss-it hillside restaurant are Buba’s house, Buba’s sister’s house, and Buba’s Brother’s house across the street. Buba’s own two daughters, nephews, cousins, and other miscellaneous family either host, help in the kitchen, play dj, man the bar, or simply greet visitors from their porches with welcoming, West Indian waves. This homegrown approach extends beyond hospitality to deliciously impact the food as well. Nearly every fruit, vegetable, and herb used in the dishes at Buba’s are all grown on the sloping overgrown gardens surrounding the restaurant. The result is a quintessential island restaurant with no real set menu. Instead, expect the freshest ingredients of the day lovingly coaxed into a collection of authentic Caribbean fare like rice and peas, stew chicken, steamed veggies, salad, and more.

The first in Fiji to introduce overwater bures (traditional huts made of wood and straw), adults-only Likuliku Lagoon Resort continues to set the standard for romantic luxury. At the all-inclusive property on Malolo Island, about 15 miles west of Viti Levu, couples who spring for one of those accommodations enjoy sun-bathed views over a sparkling marine reserve from the teak deck or oversized soaking tub; at night, fish are drawn to lights under the hut and are visible through glass panels inset in the floor.

Back on the beach and closer to the restaurant and two bars (one located on a small island in the lagoon), there are 35 beachfront bures, including 18 split-level deluxe bungalows that feature private plunge pools and secluded courtyards with outdoor showers. Activities like snorkeling, stand-up paddleboarding, kayaking, and sailing are complimentary; more adventurous types might also request arrangements for diving and fishing trips, island-hopping tours, sunset cruises, and visits to a local village.

On a hilltop perch overlooking 8,000 acres of grounds designed by famed landscape architect Frederick Law Olmsted, the Inn on Biltmore Estate’s 210 rooms and suites evoke traditional 19th-century manor houses, with dark mahogany beds and desks, billowing window treatments, and comfortable overstuffed chairs; book a room with a balcony to breathe fresh mountain air while appreciating views of rolling hills—or simply take in the vista from the hotel’s veranda. The formal dining room showcases seasonal specialties using estate-raised cattle and lamb, vegetables from the on-site garden, and wine from the property’s own winery, where you can participate in a free tasting, then ride back in a complimentary shuttle. If you’re looking for something more casual, the lobby lounge and library bar offer salads and sandwiches—and no dress code. But the main attraction is the 250-room Biltmore château, the Gilded Age mansion George Vanderbilt built here in the late 1800s, and its 16th-century tapestries, Renoir and Sargent originals, and 65 fireplaces.

One of the best spots to relax in Miami is Bayfront Park, 32 acres of lush grounds that include the Klipsch Amphitheater and the Tina Hills Pavilion. The Fourth of July fireworks and the New Year’s Eve countdown are just two of the community events that occur here throughout the year. From the beach you can watch dolphins jump and play while luxury yachts pass through Biscayne Bay, and you’ll also have great views of the cruise ships and marina. Take the renovated baywalk, shaded by oak and palm trees, past the rock garden and waterfall and several benches. Fitness classes are offered in the park during the week.

(Note: Google insists this is Kamuela, it is Kohala) The lava coast of Kohala on the Big Island is dramatic. Waves dash against the black rocks relentlessly until eons from now they will be sand. True, there are fewer white-sand beaches per square foot of land on the Big Island than others in the Hawaiian chain, but the island is huge. Beaches here often hold secrets, are the sources of legends, and are part of the circle of life for creatures indigenous to Hawaii. There have been lava flows since the ahapua’a land divisions were formed, but from the very tops of the mountains running to the sea, most beaches remain intact. One of my favorites is in a little inlets fronting the Mauna Lani Bay Hotel on Makaiwa Bay called Keiki Beach. Not for much swimming, it is a sandy-bottomed dipper’s delight or, as the name states, a place for children (keiki) to play in. A tree for shade, sand, tide pools to explore, a canoe house (hale) covering a koa canoe nearby, and a friendly turtle (honu) who feeds here are all part of what could be a perfect day. There is surf off the point in winter and snorkeling in other seasons. You might even want to rinse off and have lunch at the Mauna Lani pool restaurant. Parking is a good 15 minute walk via a trail. Follow signs to public parking off Mauna Lani Drive, bring water and beach gear, and get there early. Of course you could stay at the Mauna Lani Hotel and Bungalows too. http://www.maunalani.com/

After Carcassonne in southwest France, Visby lays claim to the most important and best-preserved medieval city walls in all of Europe. The town’s citizens began building the original six-meter-high (20-foot) fortified walls in the 13th century, and they eventually grew to over 11 meters (36 feet). Today, the wall still stretches for 3.4 kilometers (2.1 miles). Walk in its shadow and explore the 36 intact medieval towers as well as numerous gateways. The North Gate offers the most impressive view of the wall, providing a sense of its enormous scale. St. Mary’s Cathedral, a few blocks inland, also dates to the 13th century.

Since its opening along a dazzling stretch of sand known as Cabbage Beach in 1962, The Ocean Club on Paradise Island has been the preferred stay of old-money patriarchs and traditionalists. Though much at the serenely posh resort has remained unchanged, the 105-room property has been modernized to meet today’s standards with spa-sized marble bathrooms, sweeping WiFi, and a restaurant run by star chef Jean-Georges Vongerichten. But it’s the feeling of a privileged, unhurried yesterday that continues to draw an appreciative upper-crust crowd. An on-site tennis pro provides tips for improving your backhand, Versailles-inspired gardens complete with a 12th-century Augustinian cloister offer moments of quiet contemplation, and rounds of golf end with martinis at the resort’s bar. These details, plus knowing that a personal butler and afternoon champagne and strawberries are included in the price, keep guests returning year after year.

Located on seven-mile-long Estero Island, Fort Myers Beach is precisely the sugar-sand playground you come to Florida’s Gulf Coast to enjoy. Named among the best in America, the beach is long and wide, making it perfect for a stroll or bike ride—especially at low tide. Vendors here sell everything from umbrella and chair rentals to parasailing adventures and eco tours. There are also accommodations, including hotels, inns, and small, family-run motels to fit nearly every budget.

Momogoose had to be one of the first food trucks around. Founded in 1989 by MIT alums, it’s only natural they would take a scientific approach to cooking. Their barbecued tofu is just the way I like it: chewy, moist and very meatlike with a sauce that’s equal parts sweet and sour. When I’d finished, I realized that the dish had made a convert out of the carnivore in me. I also love the fact that they have a “Meal for Meal” initiative providing nourishment to the global poor through the World Food Program.

Located on the edge of the Adams-Morgan neighborhood, this saloon features library-style shelves of over 1,400 varieties of whiskey from floor to ceiling. Single Malt and Blended Scotch, Irish, Canadian, Belgian, Japanese, Indian, Welsh, and American (bourbon and rye) flavors are provided in one or two ounce pours. If whiskey isn’t your drink of choice, craft beers and cocktails are available as well. Aside from the main bar, it features a whiskey cellar, a tiki bar, and an open-air roof terrace for drinks and cigars while witnessing the revelry below on 18th Street.