Rome
For a place that calls itself the Eternal City, Rome has taken an unabashedly modern turn. At the Centrale Montemartini (centralemontemartini.org), an old electricity plant has become a stunning industrial home for “overflow” antiquities from the Capitoline museums. Take in works by Francesco Clemente, Anish Kapoor, and other contemporary masters at the Zaha Hadid–designed Maxxi museum (fondazionemaxxi.it). And then there’s the city’s latest attempt to update its ancient past: the Palazzo Valentini (palazzovalentini.it), which uses light displays to reconstruct what ancient villas would have looked like. Give in to your lust for tradition with dinner at Testaccio’s Flavio al Velavevodetto (flavioalvelavevodetto.it), an elegant osteria (and favorite of Slow Food founder Carlo Petrini) serving Roman classics like rigatoni alla carbonara and sauce-smothered oxtail.
Where to Stay
Live like a medieval noble in a three-bedroom Trastevere palazzo, still with original wooden beams and brick arches—as well as a home gym, large-screen plasma, and complete kitchen (from $320; airbnb.com/rooms/84226).
Sleep in slick modernity in a spacious two-bedroom near the Colosseum, outfitted with a computer and internet, and lots of purple accents (from $105; airbnb.com/rooms/163008).
The family that owns Guesthouse Arco de’ Tolomei has outfitted the B&B with their own antique furnishings, paintings, and china (from $195; bbarcodeitolomei.com).
Paris
Mix it up with real Parisians at the city’s grassroots art galleries, design shops, and music venues. Bookend your day with a café crème at coffee shop–concept store Merci (merci-merci.com)—a former factory space selling local artwork, quirky home designs, and discounted YSL ready-to-wear pieces—and a handcrafted cocktail at Le Pompon (39 Rue des Petites Ecuries), an abandoned synagogue turned dance club co-owned by a member of art collective Pain O choKolat. In between, check out La Gaîté Lyrique (gaite-lyrique.net), a digital-art museum that opened earlier this year inside an opulent nineteenth-century theater. Skip the months-long wait for reservations at Basque chef Inaki Aizpitarte’s Le Chateaubriand and instead slide up to the bar at his more casual Le Dauphin (131 Ave. Parmentier) next door. The Rem Koolhaas–designed glass-and-marble box is a suitably modern setting for the Basque chef’s playful spins on French classics.
Where to Stay
The Sleeping Lion, a carefully assembled apartment in Marais, is outfitted with neoclassical furniture and soft yellow lighting(from $141; airbnb.com/rooms/161668).
Gaze down at the hip young throng on the banks of Canal St. Martin from the balcony of a sleek sixth-floor penthouse (from $127; airbnb.com/rooms/148753).
Book one of the tiny, colorful rooms at Hi Matic (above, right), French design maven Matali Crasset’s new Japanese-influenced boutique hotel–upscale hostel in Bastille (from $190; hi-matic.net).
Hong Kong
There are many good reasons to visit Hong Kong—proximity to fabulous beaches, a spellbinding skyline, mind-blowing street food—but the biggest among them might be the shopping. Start in Kowloon for custom-made togs at Sam’s Tailor (samstailor.com), then accessorize with bangles, cuff links, or draping necklaces at the 400-stall Jade Market (Kansu and Battery Sts.). In nearby Mong Kok, visit the Yuen Po Street Bird Garden, where older men tend their feathered pets (not to mention their writhing bags of grasshoppers). For lunch, wing it to Tim Ho Wan Dim Sum Specialist—at $8 per person, it’s reportedly the least expensive Michelin-starred restaurant in the world (852-2332-2896). Then take the MTR to Hong Kong Island for designer goods at the International Finance Centre, or for paper versions of them along Queens Road West—you burn the miniature Bentleys, Gucci bags, and flat-screen TVs so your loved ones can have them in the afterlife.
Where to Stay
For jet-setting parents, this one-bedroom in a doorman building has a separate study with available crib, washer-dryer, and a maid (from $148; airbnb.com/rooms/113789).
In Kowloon, the East Tsim Sha Tsui district two-bedroom has 180-degree Victoria Harbour views and a pool deck (from $1,295 per week; vrbo.com/220532).
Each of the 54 studios and suites in the Philippe Starck–designed JIA Boutique Hotel has a kitchenette (from$205; jiahongkong.com).
Montevideo
Wedged between South America’s giants, Argentina and Brazil, little Uruguay is often an afterthought. But the capital’s Ciudad Vieja district has some of the continent’s finest architecture: Stop by Palacio Salvo (palaciosalvo.com), a colossal gothic and neo-romantic landmark, and take in the city’s Art Deco gems along Avenida 18 de Julio (be sure to gawk at Palacio Díaz and Palacio Rinaldi). For culture, hit up Museo Nacional de Artes Visuales (mnav.gub.uy) in Parque Rodó or an opera at Teatro Solís (teatrosolis.org.uy). Come afternoon, snack on a massini, a classic Uruguayan cream-and-caramel cake, at Carrera (5982-400-2859), then move on to gigantic grass-fed steaks at Mercado del Puerto (mercadodelpuerto.com.uy) before attempting your best tango at Baar Fun Fun (barfunfun.com).
Where to Stay
The Punta Carretas four-bedroom villa (from $300, seven-day minimum; vrbo.com) comes with two noteworthy perks: a private cook and a treehouse.
Enjoy rivers views from the deck of this very Selby-like three-bedroom loft in Old Town (from $200; airbnb.com/rooms/229557).
The country-club-like Le Bibló (from $295; lebiblo.com) is two blocks from the beach and has a pool crawling with kids.
London
As most Olympics cities have done, London is using the 2012 Summer Games as an opportunity to tidy up its gritty fringe, namely East London. But for a glimpse of more authentic London scruff, take the tube northwest to still-edgy Dalston and catch an Off West End show at Arcola Theatre, home to two performance spaces in a former paint factory (arcolatheatre.com). Skip next door to Café Oto for a local microbrewed Kernel IPA and some folk banjo or improvisational jazz or whatever eclectic act happens to be onstage (cafeoto.co.uk). Best souvenir: a screen-printed poster produced at the Print Shop nearby and sold in the artist collective’s Brick Lane store just a few stops south in Shoreditch (printclublondon.com). Sate your appetite for pig trotters at the nearby Brawn, serving locally sourced fare on a daily written menu (brawn.co).
Where to Stay
Owner Johnny Matos, who lives upstairs, acts as personal concierge at Johnny’s Place, a cozy bilevel three-bedroom in a Georgian-era Kennington address with a private garden off the kitchen (from $315, four-night minimum; flipkey.com).
From the roof of this one-bedroom, two-story flat across from the Tower of London, you can survey the city from London Eye to Tower Bridge (from $210, four-night minimum; vrbo.com/39294).
The chummy waiters at the buzzy street-level restaurant lend warmth to the Fergus Henderson’s new St John Hotel and Restaurant (above, right; rooms from $379; stjohnhotellondon.com).