Sure, you could jet off to the world's most famous monuments and take the exact same selfie every other tourist posts on Instagram. Or you could embrace all the not been there, not done that our world has to offer. Here are five of the most thrilling destinations for the stylish traveller.

No. 1: GO HIGH-LOW IN CAPE TOWN
After competing against European rivals Bilbao and Dublin, the South African city of Cape Town emerged as the World Design Capital for 2014. Along with shiny accolades there will be site installations, gallery happenings and public works of art. But high-minded design has been creeping into low-culture hangouts too: Capetonian biker shop Los Muertos Motorcycles triples as an aesthetically pleasing coffeehouse and film production studio ("Love kills, speed thrills"); the House of Machines serves all your masculine needs—grooming, dressing, accessorizing, drinking—with its lifestyle shop, café and top-shelf bar (operating Thursday and Friday nights). Concept shop Latitude 33 combines Aussie surf gear, art and upscale bistro food under one civilized, well-designed roof, welcoming riders of bone shakers, crotch rockets, gnarly waves and modernist trends alike.


No. 2: GO NATIVE ON FOGO
On a remote, rugged archipelago on the eastern edge of the North American continent stands the hypermodern, hyper-hard-to-reach Fogo Island Inn, an architectural marvel of glass walls, saltbox shapes, solar panels and steel stilts that rise from the windswept surroundings (like craggy moors and rogue arctic ice floes). This is what luxury survivalist mode looks like: Every textile and piece of furniture in the 29 minimalist, ocean-view rooms is made locally by hand; the kitchen staff scours the island for kelp, mushrooms, spruce and seafood to serve you modern Newfoundland on a plate. It's the kind of place where you'll meet boat builders at the bar, artists-in-residence at the rooftop sauna and caribou just beyond the bonfire. Of course, you may prefer to watch the fog roll in from the comfort of your natural-fiber bed in front of your personal wood-burning stove. There's no FOMO on Fogo.


No. 3: GO COLONIAL IN THE CASCO
Once graffitied and gang-laden, Panama City's 350-year-old colonial neighborhood of Casco Viejo is making a comeback. Crumbling pastel facades and dilapidated buildings are interspersed with gourmet coffee shops and landscaped gardens. Savvy travelers stay at boutique properties such as the newly opened American Trade Hotel, a restored landmark building from the guys behind the Ace Hotel empire. Atelier Ace, along with Commune Design and Panama City–based Conservatorio, set out to reinvigorate not just buildings but people, reforming gang members and involving local artisans in every aspect of the restoration. Luxe details such as Frette sheets and Aesop bath products mix with handmade Panamanian furnishings and timber reclaimed through underwater logging in the Panama Canal. A 50-seat nightclub is run by Panamanian jazz ­pianist Danilo Perez.


No. 4: GO PALEO ON THE PAMPAS
Feed your carnivorous cravings at Playa Vik, an avant-garde retreat in José Ignacio, South America's must-visit bohemian beach village. Evenings are spent on the barbecue terrace, learning how to cook beef like the gauchos; days are meant for watching bronzed bodies soak in the hot Uruguayan sun. The hotel's dramatic black-stone pool hovers 32 feet over Playa Mansa and lights up at night with a fiber-optic celestial map of the Southern sky. Architecture junkies won't be disappointed with Sculpture, the double curved titanium and glass building designed by architect Carlos Ott, or the six smaller surrounding casas decked out with the owner's insane art collection: a mix of prominent international and South American artists including Anselm Kiefer, Pablo Atchugarry and Montserrat Soto.


No. 5: GO ARTSY IN CHICAGO
Art takes action on Chicago's South Side, where enterprising artist and instigator Theaster Gates continually blurs the line between artwork and neighborhood project, working as real estate developer, civic hero, wheeler-dealer and cultural archivist. Young creatives and longtime locals hang around his Dorchester Projects, on the 6900 block of Dorchester Avenue, where Gates acquired several vacant and abandoned properties for adaptive reuse. One building is now an art and architecture library stocked with books he bought from a closing city bookstore. Another, Black Cinema House, is home to a vintage-slide archive donated by the University of Chicago and a serious vinyl collection from Dr. Wax, the defunct record store. His latest project, Arts Incubator, takes shape in a 1920s corner building that is all things at once: exhibition space, concert venue, artist residency and main line for tapping into the local pulse.


This article originally appeared in the May 2014 issue of Playboy.

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Jeralyn Gerba & Pavia Rosati bring you the five hottest emerging destinations around the world, we turned to the best-traveled ladies we know: the lovely co-founders of tastemaking travel site Fathom.

Photography by Andrew B. Myers; prop styling by Kelly Arsenault