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For a small, cozy space, Osteria delle Belle Donne serves a very large bistecca fiorentina. This tiny restaurant, with stone walls and warm wood accents, is tucked on a narrow street between the Duomo and the train station. Beyond giant cuts of steak, other tasty highlights of Florentine cuisine are served here: fettuccine with wild-boar ragù, white beans, and seafood dishes. In the cooler months, traditional ribollita (a tomato-based vegetable stew thickened with bread) and budino marrone (chestnut pudding) appear on the menu. The wine list is Tuscan, too, so it’s easy to find pairings for the rustic meals.

Old San Juan may look, at first glance, like a few other charming cities built during the height of Spanish colonialism—Havana or Santo Domingo, for example—but what sets it apart is the extent to which its architectural infrastructure from that era remains visible. It’s the only city that has its original colonial wall almost entirely intact, and both of its principal forts are in excellent condition, remain accessible to the public, and offer panoramic views of the Atlantic Ocean (so bring your camera). Both El Morro and Fuerte San Cristobal are run by the National Park Service; guided tours will leave you with greater knowledge about the era, as well as the forts’ construction and their role in Puerto Rican history. (There are other, smaller forts in and around the capital, next to the Caribe Hilton, and in Luís Muñoz Rivera Park, plus Fort San Juan de la Crúz in the nearby town of Cataño.)

On the west side of Arenal Volcano, this 900-acre tropical reserve was a labor of love for owner and architect Jaime Mikowski, who spent years planting acres of native plants and coaxing the land’s natural mineral springs into a river that now flows throughout the property, spilling over into dozens of waterfalls and pools that range from 72 to 105 degrees. Spacious rooms have marble floors and streamlined furnishings; splurge on a suite, which features a private terrace and a Jacuzzi tub—a little superfluous considering all the other options for soaking in warm water here, but who’s complaining? There are also five swimming pools, one with a swim-up bar and waterslide, and a spa comprising 12 bungalows with treatments that all include, you guessed it, a dip in a thermal spring-fed tub. While the property is also open to day trippers, guests of the resort have exclusive access to Shangri-La Gardens, an adults-only lounge area with pools, cabanas, and a folliage-filled bar.

This tiny island is north of Isla Mujeres and Cancun and is only 26 miles long and offers visitors in search of a “Robinson Crusoe” experience the perfect escape. Long, sweeping beaches beckon with water sports, snorkeling, sport fishing, and total R&R. A shallow lagoon gives sanctuary to thousands of flamingos, pelicans and other exotic birds and creatures, allowing visitors the perfect spot in which to commune with nature. Several good restaurants and hotels are available and tours to area attractions can be arranged by ferry and small plane. Getting around the island is via bicycle or golf cart.

Nuzzled up against the Arizona border about 100 miles west of Four Corners are some 30 square miles of the most iconic scenery in the American West. Monument Valley is one of those places that you’ll recognize as soon as you see it, even if you’ve never been there before, as dozens of movies, TV shows, and even video games have used the area as a setting. It’s made up of mesas both small and large reaching up from the valley floor, some rising as high as 1,000 feet into the sky. Part of the Navajo Reservation, the area charges a $20-per-vehicle entrance fee to drive the dirt-road loop. Once in, however, you can also enjoy a number of hikes, or hire a guide for a horseback tour.

The Rossio railway station was designed between 1886 and 1887 by Portuguese architect José Luís Monteiro. It makes connections with the village of Sintra, and the 2,600-meter tunnel was excavated under the city. It is considered one of 19th-century Portugal’s most important works of engineering. It has a beautiful Neo-Manueline façade, where two intertwined horseshoe portals stand at the entrance, a clock sits in a small turret, and the sculptural decoration is abundant. Inside you can now find a Starbucks, Lisbon Destination Hostel, and a souvenir shop.

Hungry locals cram this Willemstad lunch spot every weekday, but the lines are well worth the wait. The massive outdoor food court hosts six different kitchens serving up local fare on an open flame. You can’t go wrong no matter which stand you pick—this is the place to sample authentic Curaçao cuisine at an affordable price. Try a bowl of kadushi (candle cactus) soup, or a plate of red snapper or goat stew with funchi (polenta), and an arepa di pampuna (pumpkin pancake) for dessert. Walk it off by checking out the nearby Floating Market or Punda Museum after lunch.

The first monks of this abbey planted vineyards here back in the middle of the 11th century, and though the focus of the property has changed—it’s now privately owned, and home to a small hotel and restaurant—the winemaking tradition is still going strong, and is still based on the organic philosophy that’s been in play since day one. Guided tours and tastings are open to non–hotel guests, and include a visit to the historic cellars and the beautiful Renaissance gardens, along with a sampling of the estate-grown wines and olive oils. Cooking classes are also available, and from March to October you can enjoy a four-hour vineyard walk—including tours of the abbey and gardens, the frescoed hall, the aging cellars, and the winery, followed by a picnic lunch overlooking the Chianti hills.

This lovely state park stretches along the rugged volcanic shoreline of western Maui, three miles from Hana. It’s best explored on the 2.2-mile hike that starts at the black-sand beach and follows the dramatic coast, passing lava tubes, rock arches, blowholes, and Polynesia’s largest heiau (an ancient Hawaiian temple) along the way. Avoid standing too close to the geysers as well as the lava benches near the ocean, which can crumble easily, and watch out for high surf. If you’re looking to cool down after your trek, take the loop trail to the park’s freshwater caves, where you can explore two separate chambers (the first tends to be clearer and more inviting).

No hotel in Jamaica blends better with its surroundings than the aptly named Rockhouse, a string of villas clinging to the top of a sea cliff at the western tip of the island. Local stone, timber, and thatch are the building materials, and a harmony of design and setting is the result. The feel is rustic, but not rough (the showers might be outdoors, but the rooms are air-conditioned), and the feeling carries over to the pool, which sits on a rock platform halfway down the cliff face, from where sunbathers can don snorkel and mask and clamber down into a usually calm Caribbean. Even the restaurant hangs over the water, adding emphasis to the promise of dishes being fresh from the sea.

As does practically every hotel in Jamaica, Rockhouse has its celebrity stories, going back to the early ‘70s when Bob Marley, Bob Dylan, and the Rolling Stones added their names to the guest register. But it wasn’t until 1994, when a group of Australian owners took over, that Rockhouse began to evolve its reputation as one of the most Jamaican of Jamaican hotels. It happened in part because Rockhouse has none of the formality that some of the island’s best-known hotels, with their British colonial roots, still possess. And in part because of its active role in funding local education projects, it’s a valued, and popular, part of the community. That, and the restaurant’s homemade jerk sausage is legendary.

A few green acres of valuable Midtown Manhattan real estate affords office workers and visitors with valuable peace and space, two things that are hard to find in the surrounding streets. Bryant Park shares the block between Fifth and Sixth avenues and 41st and 42nd street with the main branch of the New York City Library (also worth a visit). The library runs an al fresco reading room along the north end of the park, and occasionally hosts readings and author events. In summer, a stage at the western edge of the vast green lawn runs a busy schedule of performances and films. In winter, the lawn becomes an ice skating rink and the site of a busy holiday market. All year round, the park is a popular destination for the bocce ball courts, ping pong tables, small carousel, food kiosks, open lawns, gravel paths, seasonal plantings, and a graceful fountain. It may be a challenge to find a seat at lunchtime, but it’s worth the wait. Take a break from your walk and enjoy some great people-watching, as well as shade and a measure of serenity in a green space bound on all sides by tall buildings.

The Berns knows how to party. A Gilded Age palace of luxury and hospitality in the center of Stockholm, the opulent building began life in 1863 as a restaurant, before transforming into a hot nightlife spot. When it was reinvented as a decadent boutique hotel filled with understatedly luxurious modern decor (there’s that signature Scandinavian style), the Berns combined those pasts, opening not only one of the city’s top restaurants—in a previous iteration, Asiatiska was Sweden’s first Chinese restaurant—but some of its coolest bars and dance clubs, one of its most sought-after concert venues, and some of its most exclusive electronic music clubs. Suffice it to say that, although the gilded, airy main bar and dining room is always lively, filled with attractive, designer-clad Swedes, the building practically buzzes come evening. Not that any of this scene disturbs the rooms upstairs, because the second most important part of a good night out is a good sleep, and the Berns doesn’t disappoint there, either.

Katara Amphitheater located in the Katara Cultural Village, also known as the Valley of Cultures, is paradise for architecture buffs and those on a tight budget as the entry is free. The architecture of the village is an innovative tribute to the old Qatari traditional architecture, with wind catchers providing a cooling system, overhanging roofs, dovecotes and courtyards. At the center of it all and overlooking the blue sea is the amphitheater, an architectural fuse of Islamic features and classical Greek theatre. The amphitheater can accommodate 5,000 people and has hosted open-air film viewings, dance shows and music concerts by renown artists like Vangelis, who was the special guest for the opening ceremony in 2011.

UNESCO got it right when it declared Quito’s historical center the world’s first Cultural Heritage site. Hidden among the baroque churches, cobbled streets, and colorful markets lies a square of endless entertainment. If you find yourself in Plaza Grande on Sunday, then cancel your plans for the rest of the day. From morning to night, this square, no bigger than two soccer pitches, chimes with traditional music, vendors peddling their wares, theatrical performances, and religious preachers. On stone benches, gray-bearded men strum the hypnotic sounds of pasillo music. Sprawling up one side of the Catedral de Quito’s steps, hundreds of locals watch a group re-enact Ecuador’s fight for independence. Up the other side, howls of laughter bellow against the 16th-century white walls as a face-painted comedian delivers his routine. Then, as the clouds above the Presidential Palace turn a deep red later in the day, suited men divulge the secrets of the Bible in front of studious locals.

The owners of Mama Rocks, two sisters from London with Kenyan heritage, decided to introduce the food truck revolution to Nairobi. Their pale pink truck, located most days outside the Alchemist bar in Westlands, has sent Kenyans wild with joy and praise for the gourmet burgers. Mama Rocks recipes infuse Western/American traditional foods with an African twist, like the Nollywood Suya Saga burger (a beef burger dressed with caramelized onions, arugula, and a honey and nut mayo blend), served with fried plantains on the side. Despite identifying as a burger truck, Mama Rocks turns out delicious salads and drinks, too. The veggie burger (a falafel patty topped with haloumi cheese) is one of the most popular items on the menu.