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Old San Juan offers historically and culturally significant experiences including a walk through 500-year-old forts, visits to UNESCO sites, historic churches, museums, the second oldest cathedral in the Americas and Ponce de Leon’s mansion. Cobblestone streets and pastel buildings are perfect for exploration during the day and variety of restaurants and shops make for a complementary evening.

When tragedy strikes—like the Paris terrorist attacks or the Parkland mass shooting—Nalu’s South Shore Grill creates mile-long leis from local ti leaves for those affected. Representatives then present the leis to the victims personally, while offering chants for healing. Oftentimes, the restaurant also creates the leis to celebrate accomplishments, like the return of the Hawaiian canoe Hōkūleʻa after its three-year, round-the-world voyage. Aside from being a beacon of humanitarian light, Nalu’s is a favorite for local dishes like poke bowls, island-style beef short ribs, and loco moco (a ground beef patty served over brown rice and topped with eggs, homemade gravy, and black lava salt). If you want to give back, order the roasted beet and goat cheese salad and 50 percent of the purchase price will go to charity.

This enchanting corner of Costa Rica, blessed with a superb climate, provides visitors with a chance to experience an ideal rural setting. If you’d like some action with your relaxation, you’re well positioned to hit local sights like Poás Volcano, as well as try camping, horseback riding, and trout fishing. Fraijanes Lagoon, set amid grasslands, forests, and strawberry fields, is particularly idyllic. There’s another attraction you may not associate with a rural setting: Good restaurants abound. Get up early to enjoy the sunrise and a cup of delicious coffee alongside warm bread and natilla, the local sour cream.

The Pestana Hotel Group has a knack for turning historical properties into luxe hotels; the Pousada de Lisboa is no exception. Situated on Lisbon’s grandest square, the Praça do Comércio, the 90-room property inhabits the elegant former home of the Ministry of Internal Administration. Furnishings combine clean, modern lines with ornate wall moulding and a neutral color scheme dominated by pale greens and whites. Choose one of the mezzanine rooms for views of São Jorge Castle; the high-ceilinged Suite Praça do Comércio offers sweeping vistas of the square and River Tagus from two large windows. The hotel’s RIB Beef & Wine restaurant caters to the expense account crowd, specializing in premium cuts of meat aged for 14, 28, or 60 days and served with a regional touch: Lodosa piquillo peppers. There’s also an indoor pool lined with loungers, and a spa offering a full range of treatments, including a body scrub inspired by the scents of Madeira and the Algarve.

This 12-cottage luxury hotel, 3,100 feet up in the Blue Mountains, is Jamaica without the beaches. It is the Jamaica of misty mornings, cool, cuddle-worthy evenings, and a musical heritage recognized worldwide. First as a private estate belonging to music producer Chris Blackwell and then as part of his Island Outpost collection of hotels, Strawberry Hill has been a creative refuge for performers including Bob Marley, the Rolling Stones, and Willy Nelson. After Hurricane Gilbert destroyed the estate’s great house in 1988, Blackwell commissioned Jamaican architect Ann Hodges, who specializes in historic reconstructions, to build the cottages, a restaurant, and a pool, which were opened in 1994. Yet despite the rock and roll history, and the hanging with like-minded souls up in the mountain mists, what guests seem to remember most is the far-below views of Kingston, especially at night, when the lights glow and sparkle from what must certainly be another world.

While the Liberty Hotel may have deep roots in Boston lore, it’s not for the reasons you think. For more than 100 years the hotel existed as the Charles Street Jail, an in-city penitentiary that housed (in)famous inmates like James Michael Curley, Malcolm X, and Sacco and Vanzetti. Its inspired transformation came in 2007, but the owners maintained some of the jail’s vestiges, from the exercise yard to several jail cells, while turning the building into a 298-room luxury hotel. Richly appointed rooms offer sweeping views of the city skyline and the Charles River.

The hotel houses five distinct restaurant and bar venues, all of which attract large swaths of locals, especially on the weekends. Located at the foot of Beacon Hill, the hotel is steps away from the boutique and antique stores along Charles Street and also sits next to the picturesque Charles River Esplanade.

From the subtle lighting in the lobby to the seven-story central atrium featuring works by contemporary Russian artist Ekaterina Ganchukova, First Hotel Grims Grenka has a chic, edgy vibe that contrasts nicely with the neighborhood’s Old World surroundings. Themed after each of the four seasons, the accommodations are modern and minimalist in design, with large platform beds, Bang & Olufsen TVs, and single-button mood control lighting, as well as bathrooms with mirrored walls and waterfall showers; larger deluxe rooms have broad-cushioned couches and more than enough space to entertain for those here on business, and some rooms have smart beds that allow you to adjust the firmness to your preference. Outward-facing rooms offer lighted catwalks with views of the surrounding city, while inner-facing rooms have windows overlooking the glass-ceilinged atrium and lobby bar. Don’t miss the updated Nordic cuisine (think salmon pastrami and potato and truffle soup) at Madu restaurant, followed by drinks (during warmer months) at the open-air rooftop lounge.

The name makes it sound like the driest place in Christendom, but the SAT, as it’s known by locals, is at the forefront of coolth. This giant building on Boulevard Saint-Laurent near Rue Sainte-Catherine is dedicated to electronic culture and entertainment, which means it hosts some of the best art events, dance parties and music performances in town. The top level of its four storeys includes the famous Satosphere, a dome structure that allows for mind-blowing, immersive 360-degree visual projections. Events include presentations and master classes in addition to dance nights by the likes of Borgore, Brodinski and MYD. Don’t forget to stop by the in-house restaurant, the FoodLab, which is constantly pushing the gastronomical envelope. Photo: Sébastien Roy

In the Akihabara neighborhood, giant anime billboards, towering Sega arcades, and electronics shops dominate the streets. The area’s denkiya, or electric appliance stores, boast an unparalleled selection of gadgets for gear geeks. The giant among them is Yodobashi-Akiba, an electronics megastore located directly east of Akihabara Station. Yodobashi-Akiba has nine levels of appliances, electronic toys, sports gadgets, and travel items. Check out 700,000 yen (about $7000 USD) Leicas as well as the many non-electronic offerings: lightweight kimonos known as yukata, anime figurines, bicycles, and books. The first and eighth floors offer sustenance and a break from shopping, with restaurants serving up ramen, tonkatsu (fried pork cutlet), soba, and sushi at any hour from the popular Tokyo chain Sushi Zanmai. The ninth floor is devoted to golf and baseball, complete with a driving range and batting center.

My idea of a good time is getting lost in the woods all so I can spend a few days finding my way home, but I can’t deny the allure of glamping – especially when it comes packaged up in the form of the Kings Canyon Wilderness Lodge, the Northern Territory’s answer to rustic chic. The luxury eco-cabins – fully heated and air conditioned – are wonderful, but there’s little reason to tuck yourself away inside when you can sip Aussie wine by the fire, or enjoy a gourmet meal under starry skies (or in the lodge restaurant on chilly winter nights). The last thing I expected to tuck into in the Outback was a spicy prawn curry, but I shouldn’t have been surprised – the Northern Territory has plenty of tricks up her sleeve.

Stylish, secluded Likya Gardens is a hideaway amid the cliffs of Kalkan, a humble old fishing town on Turkey’s Turquoise Coast. Each of the seven suites has its own pool and a patio set on stilts, offering views of a crystal-blue bay and brightly colored fishing boats. Guests can sun on nearby beaches such as Patara or Kaputaş, or enjoy the privacy of the hotel’s beach club, where Moroccan-style cabanas are tricked out with minibars, laptops, and Wi-Fi. Personal butlers can deliver breakfast and book tables at the town’s rooftop restaurants; they’ll even arrange day trips to the Hidden Canyon, with its Indiana Jones–style swinging bridge. From $450. This appeared in the June/July 2014 issue.

If there’s a hub of the hubbub in Kennebunkport, it’s Dock Square, a colorful jumble of onetime fishing shacks that now house galleries, stores, and restaurants. Prowl through the shops to find unusual clothing, distinctive souvenirs, fine art, crafts, taffy and fudge, pottery, canvas bags, specialty foods, presents for pets, and, of course, the usual trinkets and T-shirts. Most of these spots are built on wharves over the tidal Kennebunk River, and it’s worth climbing to second-floor ones, such as Good Earth, for the water—or mudflat—views. The bridge connecting Dock Square to Kennebunk’s Lower Village offers another good vantage point, and the Clam Shack is one of the area’s best places to indulge in fried clams or a lobster roll.

The sprawling contemporary museum, MASS MoCA, is responsible for bringing North Adams to life, and offers some of the most cutting edge art around. Xu Bing’s Tobacco Project {above} is made from over half a million cigarettes arranged to mimic a tiger skin rug. It makes a thought provoking statement on the global tobacco trade, luxury and colonialism, and is typical of the installations you will see there. The complex also hosts a variety of musical events including dance and films. Luckily Split, the in house restaurant has coffee, treats and tasty lunches.

If you’ve been pacing up and down the passages of the Grand Bazaar contemplating that perfect purchase, chances are you’ll need refueling eventually. Hidden on a backstreet just outside gate 16 of the Grand Bazaar is the cozy and charming Keyf-i Mekan Cafe and Restaurant. “Keyfi” means “merriment,” but in Turkey keyfi is also a way of life, one that’s full of pleasure. So expect the small menu featuring delicious Turkish-style home-cooked food to fulfill both these meanings. The food will surely fill the belly and energize you to take those bazaar vendors head on! Choose from the menu of mezes, or meat dishes or peek at the mouthwatering “specials of the day” on the counter. The cafe is open every day, except Sunday when the rest of the bazaar is closed too.

One of the delights of Valparaíso is exploring the colorful hillsides that ramble down towards the sea. Take the century-old funicular elevators Ascensor Concepción (Turri) or El Peral near the main plaza, constructed between 1883 and 1911. Once high into the hills of Cerro Concepción & Alegre, explore the meandering alleyways and cobblestone streets on foot. There are boutiques, cafés, mom-and-pop shops, old school bakeries, bars, restaurants, art galleries, and church bells tolling. It often feels more like a small village than a city. Climb up and down the many staircases often lined with bright graffiti. In the distance, the bay gleams in sunlight and the busy port never tires. At dusk, the lights twinkle like fairylight. Grab a table at a spot like Café Turri for a view of the sunset and a cocktail.