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Located in historic downtown Williams, Arizona, just outside of Grand Canyon National Park, Red Raven Restaurant is cozy and casual with a brick exterior painted fire-engine red. The kitchen is small but sends out gourmet comfort food to diners seated in its high-ceilinged dining room. They tuck into dishes such as portabella and zucchini fries with a balsamic reduction sauce, broiled pork medallions topped with cilantro pesto and tempura-style broccolini, and a lamb and vegetable stew made with Guinness. Seating at this husband-and-wife–owned establishment is limited, so definitely call ahead.

Cooked in an open pit over pimento wood, the jerk preparations here are all authentic and—according to most locals—the best on the island. Traditionally spiced chicken and pork, as well as a less fiery fish version, served in a tin container along with rice and peas and festival bread (akin to hush puppies). Getting your order to stay means eating while perched on wooden barrels, which certainly adds local flavor. While enjoying the delicious meal, you’ll get to observe the seemingly endless line of customers, and perhaps get a ringside view of a lively and noisy game of dominoes.

Negril’s Kool Runnings Water Park is a nice addition to a town where the beach is otherwise the main attraction. Ten varied theme slides of up to 40 feet in height—try the “Bolt lightning”—keep everyone having fun in the water. There’s even a lazy river, ideal for the smaller kids, and three restaurants. It’s a fun place for everyone. Check their website and social media pages for group specials.

Take one evening to skip the usual beach sunset. Instead, hop on a guided glass-bottom boat and ride down the Negril River. You’ll start where the river meets the sea on the edge of Seven Mile beach, and cruise down its banks. Take in the gorgeous scenery of mangroves and birds flying against a yellow sky. The ride lasts about an hour and you’ll likely be the only one there, away from the clamor of tourists.

Hyperlocalism has fueled Portland’s Old Port District revitalization, with buzzy restaurants and shops with a deep sense of place opening in recent years. The stylish Press Hotel is no exception. A publishing motif runs throughout the 110-room property, which occupies a corner building that once housed the Portland Press Herald. Custom-made wallpaper printed with old headlines adorns the corridors, and desks inspired by those found in 1920s newsrooms are in each room. Works by local artists—including a dramatic installation of vintage typewriters from the late 19th and early 20th centuries by Portland artist Erin Hutton—and woven-wall tapestries by Portland home-goods designer Angela Adams also abound. (There are even a few notable—and welcome—nods to the global luxury market, including Frette linens from Italy atop the plush beds.) The focus at the 65-seat hotel restaurant, Union, is proudly farm- and sea-to-table, with dishes like house-smoked local mussels served with celery cream.

Driving along the countryside in northern Portugal near Oporto I saw the spectacular hillside vines of the famous Douro Valley spread out in front of me for miles. The sight was breathtaking. I saw the steep hillsides with the vines on the terraces. The vines were loaded with grapes that in a couple of weeks would be ready for harvest. The vineyards were first established in the 12th century by Cistercian monks. There are numerous Cistercian monasteries in the area. UNESCO declared the Douro Valley a World Heritage Site in 2001. The Douro Valley produces the grapes for port, red, and white wines. Douro tours are available and run from a few hours to a few days. The cruises run from April to October. If you want to see the harvest picking of the grapes plan your tour for September. A drive through the Douro Valley or a cruise down the Douro River is an experience to savor. If you get to northern Portugal, look into a side trip to the Douro. You won’t be disappointed.

If you’re fascinated by the Wild West, you’ll love this fantastic museum, where culture and history come together to transport you back in time. Named in honor of late Texas governor Dolph Briscoe and his wife, Janey, the museum is located along the River Walk, inside San Antonio’s first public library. In addition to hosting exhibitions, educational programs, and special events, the Briscoe features a Wells, Fargo & Co. Nine-Passenger Western Mail Stagecoach replica and the beautiful McNutt Sculpture Garden, which brings the West to life through intricate bronze pieces.

Walt Disney World’s four remarkable theme parks are part of nearly 104 square kilometers (40 square miles) filled with entertainment. Magic Kingdom is home to the iconic Cinderella Castle and has six themed sections. At EPCOT, guests take a trip around the globe and into the future via exhibits, rides and events. Disney’s Hollywood Studios is a working film, television and radio studio lot that features attractions based on favorite Disney characters. Adventures with real animals await guests at Disney’s Animal Kingdom. The resort is approximately 90 minutes from Port Canaveral.

Built in the 1920s by a Croatian businessman, Palacio Astoreca underwent two years of refurbishment and restoration before opening its doors as a boutique hotel in 2012. The work was carried out to a meticulous degree, maintaining the original parquet floors, and adding splashes of color with art deco furniture and modern art, including one piece by Switzerland’s Frédéric Clot. The stucco-and-brick mansion rises up from the streets of Chile’s port city, Valparaíso, like a piece of red-and-white confectionary.

A statement staircase winds up to the 23 rooms, some of which have stand-alone bathtubs. And the basement level is home to a small spa with an open-air, wood-fueled hot tub set alongside a living wall. The reception level and entrance hall open out onto a terrace where lunch, tea, and cocktails are served, allowing guests prime views over the hilly city and Pacific Ocean. There are quiet corners for those seeking a solitary moment, including a library and a piano bar, which comes to life in the evenings with live music.

Baseball had nothing to do with the naming of Fenway Park: The stadium gets its moniker from the nearby Back Bay Fens, a stretch of saltwater marsh in the heart of Boston that was landscaped into a park by Frederick Law Olmsted. The Fens are among the wilder parts of the Emerald Necklace, 1,100 acres of parklands running from the Charles River to Brookline that include familiar spaces like the Boston Common and Boston Public Garden but also less-traveled (by visitors, anyway) sections like Olmsted Park, Jamaica Pond, the Arnold Arboretum, and Franklin Park. The arboretum, part of Harvard University and established in 1872, is one of Olmsted’s most unaltered terrains, with paths running up and around 261 acres of woodland interspersed with a curated collection of trees, plants, shrubs, and vines native to New England.

Tucked into the ancient, magical maze that is Old Acre, the Efendi Hotel looks out onto the city walls and the sea just beyond. Combining two Ottoman palaces, this labor of love from celebrity chef Uri Jeremias—whose nearby restaurant, Uri Buri, is practically a foodie pilgrimage site—took restorers and artisans the better part of a decade to complete under the watch of the Antiquities Authority. The layer cake of history beneath the hotel includes a 12th-century Crusader cellar, where you should head for a wine tasting, and a 400-year-old hammam, where you should book a Turkish bath. Also not to be missed at the Efendi: the 19th-century fresco commemorating the debut of Istanbul’s Orient Express station, the gorgeously preserved ceilings, and the rooftop bar (be sure to go at sunset, when your drinks will be accompanied by a chorus of Muezzin calls). Though you’ll be tempted to linger over the sublime views—and fresh dates—in your room, get out during the day and explore the surrounding alleys, mosques, synagogues, markets, tunnels, fortress, citadel, and port.

Marché aux Puces de St-Ouen, aka Clignancourt, is Europe’s largest flea market and the city’s favorite place to find a bargain. Exiting the Métro at Porte de Clignancourt, those in the know pass by the counterfeit designer-goods hawkers, avoid the parking lot with camper vans full of cheap goods, and head under the overpass to Rue des Rosiers. Groups of stalls form smaller flea markets, each with its own specialty, so shopping can feel like walking through a museum where you can actually buy things. The market called Serpette draws serious dealers looking for mid-century marvels, but shoppers who head as far as Jules Vallès market may score some true bargains. Of course, this is France, where food matters, so there are plenty of local cafés to choose from. Ma Cocotte is trendy chic, La Chope des Puces has live jazz with moules frites, and Chez Louisette draws a crowd nostalgic for French tunes with its simple steak frites.

From the porte-cochère entry at the Westin Puntacana Resort & Club, you’ll catch an inviting first glimpse of coconut palms, manicured grass, and a long swimming pool that seems to end at the sea. The view only gets better upstairs, where all 200 rooms—including 16 suites—offer swoon-worthy ocean vistas. On the hottest of days, the high-ceilinged, open-air lobby is a great place to hang with a cold one while catching the ocean breezes. When it’s cooler, have lunch by the pool or at the beachside La Palapa, and plan for dinner at the open-air Brassa. As a guest at the Westin, you also have access to Puntacana Resort & Club’s eight restaurants, two golf courses, tennis center, Six Senses Spa, aquatic center, and Grupo Puntacana Foundation activities.

A stroll of St. Kitt’s capital, whether started at Port Zante Marina or the centrally located Independence Square, is an entertaining way to learn more about the island’s past. While the French named Basseterre (it means “low land”), the British are responsible for the town’s most recognizable landmark—the green, cast-iron Berkeley Memorial Clock in the center of the Circus, where several streets intersect. Make sure to visit the area, as well as Independence Square, St. George’s Anglican Church, and the Old Treasury Building, which now serves as the National Museum of St. Kitts. Along your walk, you’ll also find duty-free shops and local boutiques, plus a lively produce market by the waterfront if you come on the weekend.

Despite the industrialized patty chain stores across Jamaica, the love for handmade patties continues in some parts of the island. Miss Sonia’s entrée-size, crusty patties are served at a small roadside restaurant across from the beach in Negril. She offers traditional fillings like beef or callaloo, as well as others like lobster and conch that she introduced at the suggestion of her numerous return visitors to Jamaica. When you get your order, be sure to shake on some of the secret spicy sauce—Miss Sonia won’t tell you what’s in it—and then dig in.