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Negril, or the “Capital of Casual” as it’s known in Jamaica, is everyone’s favorite getaway, from locals to the visitors who return year after year. The buzz of activity on Seven Mile Beach’s powdery white sands is tempered by the breathtaking, serene views of the West End’s cliffs towering over the Caribbean. Lots of bars, hotels, and restaurants line Seven Mile Beach, and local eateries and smaller boutique resorts are perched up on the cliffs. While there’s more hustle and bustle and throngs of tourists on this end of Jamaica, the region still offers many secluded spots and unique experiences.

Step inside the Eye Film Institute to discover an homage to international cinema replete with interactive displays and perched like an ivory spaceship ready for launch on the northern bank of the IJ River. The striking facility, accessible via a free ferry from the main train station, houses four movie-screening rooms, a museum shop, and an exhibit space showcasing the works of masters like Fellini and Kubrick. Topping the contemporary structure is the eye-popping Eye Bar-Restaurant, where you can wash down a plate of bitterballen with beer on tap while musing about cinematography. On sunny days, a spacious terrace beckons.

From the dusty street, the Hotel El Convento in León, Nicaragua, beckons with its stately façade and red Spanish-tiled roof. Step inside and you instantly feel at home amidst ornate period furnishings that are surely a far cry from the building’s humble beginnings as the 1639 San Francisco Convent. The elegant Restaurante El Victoriano offers an indoor-outdoor retreat centered on the hotel’s manicured, tropical courtyard—an example of the colonial hacienda style found throughout León. The restaurant is a meeting place for people from all walks of life—aged former Sandinistas who now hold positions of leadership, locals splurging on a fine meal, or foreign students from one of the city’s many Spanish language schools seeking tranquility and an excellent cup of coffee.

Long the heart of the Condesa district (even during the dark days following Mexico City’s devastating 1985 earthquake), today’s Parque México is the quintessential urban park. Well-manicured with ample seating and a recently refurbished open-air forum that plays host to groovy neighborhood events as well as perennial skateboarders, the park’s venerable trees provide shade to the area’s easy-on-the-eyes crowd of joggers, dog walkers, cute old folks, and amorous teens. Along the garden’s perimeter, some of the city’s smartest apartment houses (often in flawless art deco style) share space with cool cafés, kicky boutiques, and crowded restaurants. Few city pleasures surpass Parque México’s people-watching (and pooch-watching) over coffee or cocktails, as golden sunlight streams through branches onto lively, see-and-be-seen sidewalk venues.

The interior of the Catholic Church of the Assumption, in the heart of Soufrière town, will surprise with its decidedly Caribbean hues and French design: an ornate wood ceiling vaulted to resemble the ribs of a boat, baby blue pillars, and brightly colored stained-glass windows. Visitors are welcome to join in the Saturday evening mass at 6:30 or Sunday morning mass at 8:30, both with the sermon in English and Creole. A quick and respectful tour is also possible at other times to admire the architecture, including the partially blue-painted exterior. While there is no printed information on the church inside, it’s worth a stop.

Wish that your one-stop shopping and dining location had high-concept ice cream, ramen, and New York–style pizza? Look no further than Pine Street Market, Portland’s first modern food hall. Home to some of the city’s best-loved restaurateurs, it counts among its popular food stands Wiz Bang Bar (featuring the nation’s only high-concept soft serve from the folks at Salt & Straw), Bless Your Heart Burger (done Carolina-style, from Toro Bravo’s John Gorham), and OP Wurst (from local wurst-meisters Olympia Provisions). The 10,000-square-foot space in the renovated 1886 Carriage & Baggage Building is listed on the National Register of Historic Places and was the site of the Old Spaghetti Factory until 1981.

The stationery shop Itoya resembles a museum, with its exquisite displays and handsome collection. The main shop on Chuo Dori has 12 floors of paper, stationery, pens, planners, and a café. The annex on the backstreet has seven floors of paints, colored pencils, notebooks, and more. Itoya is a great spot to pick up gifts for friends back home. It’s easy to find—just look for the giant red paper clip in front of the building.

It’s the wine. It’s not just the small houses with baroque detailing, or the cobblestoned streets with old trams that wind their way up the Vienna Woods foothills, that make Grinzing the most popular of all of the former villages that have been absorbed into present-day Vienna. The city has by some counts more urban vineyards than anywhere else in the world, and Grinzing’s famous Heurige (wine taverns) draw big crowds. The proprietors of Zum Martin Sepp, across from the parish church, welcome visitors to their cozy courtyard and tavern rooms. Guests enjoy Austrian specialties such as the Kaiserschmarrn pancake dessert and drink house grüner veltliner and other wines, while swaying to musicians wielding the signature folk accordion and playing old Viennese drinking songs.

Among Andalucía’s well-known treasures are its white towns, with their whitewashed buildings glowing in the Spanish sunlight. Near Málaga at some 430 meters (1,400 feet) above sea level, Mijas, made up of several small hamlets, is one of the finest with a strong contingent of British expats. Shops in town sell pottery and other handicrafts, while a small folk museum is also a draw. After strolling the town, visitors will want to stop into one of the small tapas restaurants or local bars to refresh.

Located just off Main Street, the Washington School House Hotel eschews Park City’s typical rustic style for a pared-down, flea-market–chic aesthetic. Before being reimagined as a design-oriented inn in 2011, the 1889 building served as a schoolhouse for miners’ children and a dancehall for the local outpost of Veterans of Foreign Wars. Today, the interior is anything but traditional, from the whitewashed living room with 16-foot ceilings to the antique mirror and the white, lacquered antler chandelier. Outside, a heated pool sits on the hillside surrounded by aspens and boulders. There’s also a fire pit, fashioned from a steel Olympic torch from the 2002 Winter Games.

Each of the guestrooms and suites is unique, though all feature reclaimed wood floors, crystal chandeliers, and tall windows. An artful collection of European antiques and vintage paintings adds a bohemian vibe, while white marble bathrooms offer heated floors, walk-in showers, clawfoot tubs, and period fixtures. Guests can also look forward to plush hooded robes and top-notch toiletries from Molton Brown.

From the luxury Oetker Collection, Le Bristol is one of the first hotels in France to obtain Palace distinction. Occupying nearly an entire block on Rue du Faubourg Saint-Honoré near the Élysée presidential palace, this soulful property has been a gathering place for Parisians since 1925. The 190 guest rooms, which feel like private apartments, are decorated with precious fabrics, paintings, and 18th-century antiques. The on-site attractions include a spa by Le Prairie, a teak-lined pool resembling a yacht, and a courtyard garden fragrant with jasmine. For more than a decade, chef Eric Frechon has held three Michelin stars at Epicure, where menu fixtures include the macaroni stuffed with black truffle and foie gras. Frechon’s culinary dominions are a portal into French gastronomy itself: The hotel has its own chocolate factory, cheese cellar, flour mill, and boulangerie.

Old San Juan is known for its atmospheric and historic hotels, but none quite match the Gallery Inn for personality and creativity. Composed of six intertwined town houses, this endlessly fascinating hotel beckons guests to wander through its nine interior gardens and patios, and seven parlors and porticos. Dating to the mid-1700s, the oldest building, La Cueva Del Indio, is located above Old San Juan’s north walls, meaning the views out to sea are the same ones that captivated the conquistadors.

Owner Jan D’Esopo, is a well-known sculptor and her works dot the hotel’s meandering interior, which has enough comforts and homey character to avoid feeling like a museum. Equally unique are the 25 rooms, decorated with everything from silk screens and watercolors to sculptures and paintings. Some even feature elegant, four-poster beds and balconies with views of the ocean. Just don’t expect to watch TV—one, there are no TVs, and two, the views out over the old fortress walls are better than anything on Netflix.

The island’s first settlement, Holetown, on the west coast, is a favorite destination of shoppers thanks to Chattel Village. Beautiful old fretwork houses painted in a rainbow of bright colors have been turned into a collection of shops. Visitors can browse for gifts and souvenirs as they wander the landscaped grounds before enjoying a meal or drink at one of two restaurants.

Described by writer Tahir Shah as the “greatest show on Earth,” no visit to Marrakech would be complete without a visit to the famous night market on the Djemaa el Fna. Arrive before sunset and park yourself at one of the various cafés with terraces overlooking the square to watch performers set up; then venture into the fray in search of adventure. Silk-clad acrobats, wide-eyed storytellers, sly snake charmers, jangling belly dancers, and capricious monkey handlers all emerge from the darkness, ringing the edge of the food stalls with their own special brand of entertainment. When you tire of the heckling, prowl the market in search of good things to eat: bite-size morsels of grilled lamb rubbed in cumin, sardines fried in chermoula, peppery snails, and sheep’s heads for the brave. Then nudge up alongside a family of locals at the table and settle in for the feast. If you’re nervous about going it alone, you can sign up for a food tour with Canadian tour guide and all-round good egg Mandy Sinclair of Tasting Marrakech; she’ll help you find the best stalls while introducing you to the secrets and delights of traditional Moroccan street food.

Anguilla’s most social beach is full of local flavor. From visiting boats to residents who flock here for the best island-style bar-and-nightlife atmosphere—home to Johnno’s, Elvis’ Beach Bar, and the Pumphouse—there’s never a dull moment on Sandy Ground’s long, soft strand. The water here is calm, making it an ideal stretch of sand for families as well. Sandy Ground is also the site of Anguilla’s August Monday, the most important day of the summer carnival season, when the entire country seems to be in the same location to celebrate J’ouvert: some folks on the beach, some on boats blasting music. By 1 p.m., the August Monday sailboat race kicks off—the first round of qualifying for the final carnival boat race at week’s end.