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In 2011, one of Chicago’s most popular restaurants, Longman & Eagle, expanded into an inn with the creation of six rooms. The owners, two of whom run the music venue Empty Bottle, built and outfitted the whole place. Each of the rooms is different, but all are stylishly simple and feature details such as wood floors, exposed brick, original art work and site-specific installations by local artists, cassette players with mix tapes, well-curated minibars, and Aesop toiletries. For the noise averse, the hotel reminds potential guests that the rooms are located above “an occasionally raucous, whisky-fueled tavern.”

Less than an hour from Guadalajara, Lake Chapala—Mexico’s largest lake—offers a relaxing respite from the big city. Visitors can enjoy drinks or a meal at one of the many restaurants on the pier, watch the sunset from a sandy beach, or rent a boat to the Island of Scorpions for a different view. There are plenty of boutique hotels around the lake should you be interested in an overnight stay.

To get to Lake Chapala, catch a direct bus—they leave every 30 minutes from Guadalajara’s Old Bus Central. The air-conditioned ride through the mountains of Jalisco takes somewhere between 45 minutes and an hour, depending on traffic, and costs approximately US$5 for a round-trip ticket. Once you arrive at the Chapala bus station, the lake is about a 10-minute walk away on the main street.

With its leafy side streets, must-browse boutiques, and burgeoning food scene, Gueliz is quickly resembling pockets of Paris, particularly as more and more bistro-inspired places open their doors. Le Petit Cornichon is like a breath of spring with its splashy Majorelle blue and daffodil yellow color palette, floor-to-ceiling windows that look out onto the street, and animated atmosphere. Toward the end of the week, you’ll find half of Marrakech here indulging in a laid-back lunch before heading down to the beach at Essaouira for the weekend, but it’s a lovely place for a prix fixe lunch any old time and a good value to boot: two courses for $17, three for $21. Settle in to peruse an excellent wine list before tucking into dishes such as sea bass ceviche with grapefruit and pink peppercorns, tarragon chicken, and a sliver of wickedly rich chocolate tart.

Go shopping at Villagio Mall, an opulent Venetian-style shopping mall traversed by water canals and a fleet of gondolas offering rides to the shoppers. The Mall is inconspicuously partitioned into two sections: one geared to cater to middle class patrons which resembles an elegant shopping mall in the USA, and the exclusive side with high-end boutiques (Cavalli, Roles, Versace, Louis Vuitton, etc), French restaurants and designer jewelries, all under a lavish glass dome and flanked by balconies evocative of an old Italian town.

About 20 minutes from the center of Guadalajara is the tiny town of Tlaquepaque, whose name translates to “hills of clay.” Fittingly, it’s known for its beautiful pottery and other handicrafts. Wander around Independencia, a pedestrian-only street where the Mercado de Artesanías and several boutiques are concentrated. While in town, you should also pay a visit to the Regional Ceramic Museum, founded to promote indigenous ceramics from Jalisco.

Built in the 1930s as a private villa, this boutique hotel was renovated in 2012, but still makes guests feel as if they’re staying in someone’s home. Perched on a steep hillside across the bay from the Old Town, it features stone terraces, vine-covered pergolas, and colorful gardens, all of which offer breathtaking vistas of the Adriatic and Dubrovnik’s signature tiled roofs. The 13 rooms—all but one with sea views—have high ceilings and arched windows lined with white shutters to soften the afternoon sun, while modern bathrooms come stocked with plush bathrobes and decadent Bulgari amenities. When not enjoying their daily delivery of fresh fruit or cookies, guests can head to the bathing platform at the bottom of the stone stairs, the outdoor pool at the neighboring Grand Villa Argentina, or the spa at the Hotel Excelsior.

Mambo Beach Boulevard has more of the ambiance of a beach party than that of a conventional shopping mall. It features some 50 restaurants, bars and stores, including souvenir retailers and boutiques selling swimwear (as well as everything else you might need for a day in the sun). There are also water-sports operators, and your time browsing can be broken up by some time on the beach. There’s even a nightclub with a schedule of live performances that keeps the energy going into the afternoon and evening.

An archipelago within an archipelago is already an astonishing fact to grasp, but Îles des Saintes, made up of nine islets, only two of them inhabited, is full of yet more surprises. Hop on a daily ferry ride south from Trois-Rivieres in Basse-Terre to these gorgeous offshore islands around a stunning aquamarine bay dotted with sailboats and hugged by coral reefs. Also known as Les Saintes, these islands combine a traditional Caribbean setting of secluded beaches, forts, and towering palm trees with a chic French village lifestyle. The streets here are free of cars, the winding roads to be explored by electric scooter or on foot. Hike to Fort Napoleon for a breathtaking panoramic view over Les Saintes Bay, explore the surrounding waters by catamaran, go diving off the bluffs, sample some of Guadeloupe’s best French and Creole fusion restaurants, and shop the boutiques for French fashions and local jewelry.

Located in the charming neighborhood of Colonia Lafayette, Hotel Demetria is among Guadalajara’s trendiest boutique hotels. In addition to stylish rooms, a rooftop pool, and a popular restaurant, the hotel features a contemporary art gallery and bookstore on its mezzanine level. Even more impressive, however, is the fact that the steel-and-glass structure is sandwiched between two pieces of architectural history—Casa Franco and Casa Quiñones, designed by Mexican modernist masters Luis Barragán and Pedro Castellanos, respectively.

Housed on the wilder south side of Tahiti near Teahupo’o, Vanira Lodge is easily the island’s best boutique lodging option. Its idyllic location—on the mountain side of the road up a very steep driveway—offers sweeping views of the lagoon, while its bungalows feature a beautiful mix of bamboo, coral, rock, reed, and stained glass. Each room showcases a slightly different design; some have hard-carved furniture and, others, outdoor kitchens. There’s also a swimming pool, lily pond, and plenty of space to children to play, as well as an onsite restaurant, which is a relief to families since the resort is a good 15-minute walk away from Teahupo’o village and the surf beach. During the day, the staff can arrange a myriad of activities, from snorkeling trips to surf lessons. Guests also have access to bikes, although having a rental car makes getting around much easier.

This stylish mall is located between the iconic Zig-Zag towers. The proximity to the Grand Hyatt and the Ritz Carlton Doha Hotels, makes this mall a favorite with tourists staying in the area. It is smaller than Villaggio, Landmark and City Centre Mall, but do not let its smaller size fool you. It houses, among other exclusive boutiques, a massive Fifty One East department store offering spectacular couture, one-of-a-kind timepieces, exclusive jewelry, unique fragrances, beauty products, and even musical instruments. Lagoona Mall’s Fifty One East department store, true to its philosophy that only the finest attracts the best, redefines the word “pamper” by offering its shoppers VIP rooms, where they enjoy a private shopping experience. There are lots of beautiful benches all over the mall for those not in the mood for shopping but wanting to relax to the piano music played live from the Yamaha shop. The Mall hours are: Sat-Wed 10:00 am-10:00 pm Thu 10:00 am-12:00 am, and Fri 2:00 pm-12:00 am

For those who aspire to travel as trendsetters in Jamaica, it helps to know that Port Antonio, way out on the eastern end of the island, is the destination to head for. And the address to shelter at is the Trident Hotel, whose 13 waterfront villas would not look out of place on South Beach. Nor would the crowd that hangs around its infinity pool or in its restaurant, Mike’s Supper Club, where local musicians and the occasional celeb sit down to knock out tunes on the 1917 Ferrari-red grand piano. The Trident Castle, a kind of fantasy annex, is a former private residence whose grand rooms, sea-view terraces, and dollhouse-size chapel make it ideal for destination weddings. A hard road to get there? Not for guests who avail themselves of the helicopter pad.

It’s a sad fact that many swaths of Johannesburg aren’t exactly walkable, but that’s not the case at Melrose Arch, a trendy complex filled with some of the city’s hottest restaurants, galleries, and shops. Guests are in the heart of the action if they book a stay at the African Pride Melrose Arch Hotel, a slick property with 118 stylish, contemporary rooms adorned with modern African art. And now that the hotel falls under the Marriott family umbrella, guests can expect all sorts of perks and upgrades associated with the brand.

Located on the West End of Oklahoma City’s Film Row, 21c Museum Hotel—a 135-room boutique hotel, free contemporary art museum, and home of Mary Eddy’s Kitchen x Lounge—occupies the former Ford Motor Company Assembly Plant.

The ever-colorful Jaffa Flea Market, in operation for more than 100 years, inhabits a portside neighborhood of alleyways, covered walkways, and outdoor verandas. Wander the endless market streets to find restored antiques and handicrafts, Judaica and Persian tiles, as well as designer boutiques and art galleries. Even if you don’t buy a thing, it is the perfect spot to sample local fare. Once the sun sets, and the vendors head home, a food scene springs to life—a wonderland of twinkling lights with dozens of trendy restaurants, bars, and chic cafés. (The flea market is called Shuk Hapishpishim in Hebrew.)