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Every September, El Cosmico puts on an exuberant 3-day celebration of music, love, freedom, and everything else kick-ass West Texas. Bring your own tent, rent one of El Cosmico’s safari tents, book a yurt, or go extra glam with one of their decked out vintage trailers (those get booked early!). Trans-Pecos is relaxed, intimate, and hilarious. Being part of it makes for an unforgettable weekend in the Chihuahuan Desert, under those vast Texan skies. Last year only a little more than 1000 tickets were sold, and organizers plan to keep the event at about that size, as that’s a big part of what makes it is so special. There’s going to be a great line-up of music, off-beat workshops, vendors who’ll make you want to revisit your entire wardrobe, and, one of my favorites, the sandlot baseball game that is less about the actual game played, and more about the riotous half-time show, and of course the spectator outfits. Prices: 3 days music only: $200 3 days music + camping: $250 - tickets are per camper, not per tent 1 day music only: $75 - available only at the gate day-of-show

At the poolside restaurant Dar Moha, hungry travelers can dine on couscous with foie gras, lamb shank tagine with ras el hanout jus, and chakhchoukha, a caramelized apple tart spiced with saffron. Enjoy your meal at one of the candlelit tables while a musician plays the oud, a stringed instrument similar to a lute.

At this speakeasy-inspired cocktail bar near Chiesa Nuova, hipster bartenders pour and shake American classics like Manhattans, Sazeracs and Old-Fashioneds in a smoky lounge. To gain admittance, make a booking and come armed with the secret password, a clue to which can be found on the venue’s website. Once you enter, you’ll be shown to a table or barstool, handed a menu, and asked to fill out a membership card. Service can be slow and snarky, but drinks are worth the wait. Cash only.

Hyde Park is happening. Catering to the University of Chicago crowd and its visiting dignitaries, the five-year-old Sophy takes inspiration from hometown literary and musical heroes, whose artworks ornament the walls in the popular and always convivial Mesler restaurant. Taking the title of the first boutique hotel on Chicago’s South Side when it opened in 2018, the property occupies a prime spot on 53rd Street—a vibrant commercial hub lined with shops and restaurants owned and frequented by a diverse population that range from academics to local politicians to the city’s cultural influencers. Former UofC professor Barack Obama’s home (and his under-construction presidential library) are nearby.

This university for music was established in 1875 by, you guessed it, renowned Hungarian composer Franz Liszt. The building is of course primarily a school—but its lively in-house concert series, including chamber music, student ensemble performances and classical works for larger orchestras in several halls and spaces—assures a lot of public interaction with this place’s wonderful classical music tradition. This gorgeous, recently refurbished Art Nouveau building is packed with lovely tapestries and gold-leaf decoration, making it as much a feast for the eyes as it is for the ears.

Once a separate municipality, San Ángel—in the city’s south, nestled into its western foothills—is a leafy, genteel enclave whose relative isolation adds a soigné feel (for better or worse) you won’t find in neighboring Coyoacán. Ground zero for promenading is quaint Plaza San Jacinto, whose cute parish church (and beautiful cloister garden) is a sort of spiritual last stand amid the surrounding area’s high-toned consumerism. That said, the plaza’s true spirit comes alive Saturdays, at the so-called Bazar Sábado, an artisanal market that fills the area with stall after stall of handmade jewelry, textiles, crafts, and accessories, plus a great deal of art—some finer, some less so—in styles that go from hippie to haute. Strolling musicians and performers add to the carnival atmosphere.

At-home entertainers will enjoy the expansive digs at this Upper West Side property, where a number of studios and suites feature terraces and enough space to host upwards of 30 guests. Even its more modestly sized rooms evoke big-time comfort, though, thanks to luxury bedding, signature mattresses, and an array of everyday conveniences (think Keurig machines and free morning papers). There are plenty of perks to be found beyond the rooms as well, namely at the property’s three dining venues. Serafina restaurant excels at Northern Italian plates, while LOCL offers speakeasy-inspired cocktails alongside live piano sets and a library with an original fireplace. Guests will also want to check out RedFarm, where chef Joe Ng serves clever takes on Chinese fare and dim sum, such as oxtail dumplings and BBQ duck lettuce wraps.

You probably won’t head out to the Hipódromo de las Américas unless you’re a devoted horse racing fan, but if you do consider yourself a betting and racing aficionado, you’ll probably be glad you visited. Hipódromo de las Américas was established in 1943 and can accommodate 10,000 fans. The infield’s artificial turf is the largest such extension in Latin America, one of several superlatives attached to this venue. Cost is no barrier for fans, either: entry is as low as 10 pesos, depending on where you want to sit, and betting starts as low as 1 peso. Check the schedule to see if any major events are on during your visit; this venue is home to the Mexican Derby.

A compound-like hideaway on a leafy street a block from trendy South Congress Avenue, Hotel Saint Cecilia is a retro-glam love letter to the 1960s and ‘70s rock music scene, named for the patron saint of music and poetry. But that doesn’t mean that rock stars smash guitars and throw ragers here (unless they rent out all 14 rooms, of course); unlike at its nearby sister properties, Hotel San José and Austin Motel, only guests and club members are welcome at the lounge, a laid-back affair with a Parisian-café–style patio, chesterfield sofas and a fireplace indoors, and craft cocktails and gourmet small plates. Between the 1888 Victorian main house—originally inhabited by a descendent of Davy Crockett—and verdant grounds that hide private porches and a serene pool, the hotel feels more like an impossibly stylish artists’ retreat than a celebrity getaway.

Each distinctively decorated room is larger than many an apartment, and seems ripped from the pages of a fashion magazine photoshoot. Every detail has been thought through, from the refreshing Grown Alchemist body care products to the Swedish Hästens mattresses (the hotel is the only one in North America with them in all rooms) to the impressive library of LPs to borrow. Everyone’s a rock star, here.

The Caves, just west of Negril, is aptly named. While the 12 cottages and one villa sit atop honeycombed cliffs, the Blackwell Rum Bar, a private dining venue, and the massage table of the hotel’s Aveda Concept Spa are actually in underground grottos open to the sea. The setup is very Treasure Island, and the flicker of candlelight and the echo of waves off cave walls make it uniquely romantic. Each of the thatch-roofed cottages is as colorful as a paint box, and each gives a sense of being alone at the end of the land. This is one of music mogul Chris Blackwell’s Island Outpost properties, so the vibe at the Jacuzzi, sauna, or salt-water swimming pool is hip but relaxed. Although famed Seven Mile Beach begins almost where the cliffs end, the hotel itself has no beach, which is why a tradition at the Caves is to begin the day by jumping from the cliffs into the usually calm Caribbean below—or at least thinking about it.

Feel like learning to East Coast Swing, Salsa, Tango, Waltz or Kizomba while you’re in Seattle? From events to classes, to venue rentals and Footloose-inspired advocacy (repeal the ‘dance tax’ in Washington State), this is the perfect place for a creative date night. The organization is made up of three venues that include the Century Ballroom, the West Hall and the East Hall (pictured). Be sure to check online in advance for availability and times that certain types of lessons are taught, and then make a reservation. You’re in the perfect place for dinner as well, in that hip East Pine St and 10th neighborhood, but wouldn’t you know that the Century Ballroom owns a lovely dining spot on the same floor of the building where you’ll be dancing. The intimate Tin Table is a great spot for a cocktail and some food to fuel all of that movement. Have fun!

Mexico City was host of the 1968 Olympic Games, and today, a number of the venues used during the Games remain open and accessible to the public, including the Alberca Olímpica. Renovated in 2009, the complex is best known for its Olympic-size pool, which is open to the public for a fee, though it also has spaces for a variety of other sports activities, including martial arts, yoga, tennis, speed skating, and capoeira.

Bringing riders on a journey through the heart of the Grand Canyon since 1901, Grand Canyon Railway takes you from a starting point in Williams, Arizona, to the South Rim and back for a full-day excursion, complete with on-train entertainment from strolling musicians. Multiday packages include a Wild West kickoff show, narrated motor coach tours along the South Rim, and free time to explore the canyon on your own. Overnights take place at the Maswik Lodge North and the Grand Canyon Railway Hotel, along historic Route 66.

You can find a respectable beer selection at most Banff Avenue restaurants, but a well-crafted cocktail requires a little more intel. For a fabulous mixed drink, head to Block Kitchen + Bar on Caribou Street, an intimate venue specializing in all things shaken and stirred. With concoctions like the Gin Beetroot Sour and the Coffee & Artichoke Negroni, you’ll be glad you ventured off the main drag. You can grab tapas and gourmet sandwiches here too, like the Red Devil Calamari appetizer with spicy Thai sauce or the Kuterra Salmon on ciabatta bread. Keep in mind this teeny spot has limited seating, so arrive early or roll in fashionably late to get a seat.

Ascona, on the shores of Lake Maggiore, has swaying palm trees and a mild climate, and is Switzerland‘s lowest-lying town (643 feet above sea level). The lakeside promenade (Lungolago) offers a Mediterranean feel with streetside cafés, warm breezes, and diners clinking wineglasses—all with a backdrop of historic 19th-century merchants’ houses. The town, a former fishing village, has become an upscale resort town—known for its water sports as well as some of the best hotels in the country. Ascona’s old town center, the Borgo, is a warren of charming alleyways and chic boutiques.