Travel & Leisure
updated 12/5/2011 10:49:11 AM ET 2011-12-05T15:49:11

Don’t bother bringing the newspaper to brunch in Surry Hills—you’ll likely be seated at one of the communal tables typical of its stylish but unfussy restaurants, and a Sydneysider will undoubtedly strike up a casual conversation (and give you the inside scoop on the best spots to check out in the neighborhood). Ever since I first visited 10 years ago, it’s happened each time, perhaps because Surry Hills, just south of Sydney ’s central business district, feels more like a quaint village—albeit one with the city’s most innovative new restaurants and bars, shops, and emerging art galleries.

The area first came to life as a manufacturing hub in the late 19th century, when its narrow streets were lined with Victorian row houses occupied by immigrant workers who toiled away in the nearby sweatshops. By the 1980’s, it had been transformed into a grungy student ghetto, unloved and overlooked (in a harbor city like Sydney, the dearth of waterfront was a serious drawback). But soon stylists and designers in search of cheap rents and charming architecture began moving in. Today, Surry Hills is Sydney’s answer to London’s Notting Hill or New York City’s Nolita: a boho-chic enclave that’s temptingly crammed with under-the-radar gems. From a rollicking tapas bar owned by Australia’s chefs of the moment to a men’s wear atelier known for its razor-sharp suits, we share our little black book of where to eat, shop, and stay, plus what to see and do right now.

The Cloakroom: Gatsby meets Tom Ford at this new black-walled boutique, where Brisbane natives Josh McPherson and Andrew Byrnes sell their modern men’s wear line Pistols at Dawn. Slim-cut blazers and linen shirts are available prêt-à-porter, but the duo’s real calling card is their made-to-measure suits (turnaround time is roughly one month). You’ll also find a small selection of shoes by British label Grenson and vintage copies of Playboy on display. 47 Reservoir St.; 61-2/9212-0029.

Published Art: Carve out time to peruse this iconic bookstore, a neighborhood staple for more than a decade that stocks an encyclopedic selection of the best in the visual arts (film, photography, ceramics, and printmaking, to name a few). Owner Sharon Tredinnick is obsessive about refreshing her collection and relentlessly seeks out obscure-yet-interesting titles from around the world. 23-33 Mary St., Shop 2; 62-1/9280-2839.

Spring Court: You may recall this unfairly forgotten French sneaker brand from its heyday in the 1970’s—John Lennon was a fan, and a photo of him sporting a pair hangs in the store. Now a coveted label among the fashion-forward set, Spring Court is still family-owned and creating the same old-school lace-ups in washable canvas. An updated line in leather launched this year, but die-hard fans prefer the tried-and-true. 113A Commonwealth St.; 61-2/9281-8806.

Via Alley: Design junkies will love this trove of avant-garde and vintage products, where iPad cases featuring calligraphy-based paintings from Brooklyn artist Jose Parla are stacked alongside Japanese artist Tsumori Chisato’s animal-inspired T-shirts. For retro accessories including Colab sunglasses and even Holga film cameras, head to the mezzanine, dubbed “the attic” by owners Jane Lo and Ben Hsu. 285A Crown St., Shop 3; 61-2/8354-0077.

Bills: Chef Bill Granger’s second breakfast joint—named, with typical Aussie matter-of-factness, Bills—is a morning pit stop for hungry locals, who come for the hearty portions and low-key vibe: the chalkboard menu changes daily and you’ll find piles of well-thumbed newspapers scattered around. Don’t leave Sydney without trying Granger’s spongy ricotta hotcakes topped with slices of fresh banana and sweet honeycomb butter. 359 Crown St.; 61-2/9360-4762; breakfast for two $40.

Bodega: This Spanish-inspired restaurant is what you might consider the antipodean version of New York’s Momofuku: it’s got rock-starrish, bad-boy chefs—Australians Ben Milgate and Elvis Abrahanowicz—a foodie cult following, and the same hours-long wait for a table (sorry, no reservations). But the standout fresh tapas, such as piquillo peppers stuffed with bacalao and house-made chorizo, make it worth your while. Milgate and Abrahanowicz just opened sister restaurant Porteño Restaurant & Gardel’s Bar nearby, serving grilled-to-perfection Argentinean meats. Dinner for two $140.

Bourke Street Bakery: Jostle for counter space at this perennially packed bakery—its sausage rolls and buttery meat pies, filled with pork and fennel or beef brisket and mushroom, are some of the city’s tastiest. If you’re craving sweet rather than salty, try the house-made peach galettes or ginger crème brûlée. 633 Bourke St.; 61-2/9569-3225; pastries for two $8.

Café Ish: Spicy crocodile sausage. Precision-cut cold hiyashi noodles with shredded ham. Crisp fries dipped in wasabi mayonnaise. There’s no shortage of innovative dishes at this Japanese-Australian restaurant, a former food truck turned brick-and-mortar venue. While the offbeat menu is what draws devotees, it’s the unexpected touches that make Café Ish a must-try, from the pink-and-green-colored salts to the word “Thank-ish!” scrawled on each check. 82 Campbell St., Shop 1; 61-2/9281-1688; dinner for two $40.

Cotton Duck: At this locavore haven, the food is all organic and the industrial-looking dining room is designed with recycled timber and salvaged materials. Chef Jared Ingersoll is a pro at updating the classics—take his “borscht salad,” composed of roasted beetroot and pickled vegetables drizzled in a beef-tea dressing. 50 Holt St.; 61-2/8399-0250; dinner for two $80.

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Duke Bistro: Fashionistas flock to this funky, second-floor gastropub owned by the same team behind Aussie denim label Ksubi. Taxidermy hangs on the green-hued walls and apron-clad waitresses whisk around serving comfort dishes such as fried chicken wings with fiery Sriracha dipping sauce. Duke’s ace in the hole is its extensive cocktail list, heavy on aperitif-style drinks such as the bitter Brooklyn (a riff on a classic Manhattan made with Amer Picon). If you still have energy after dinner, head downstairs to Flinders bar for a nightcap. Warning: there’s a reason why locals refer to a wild night out as “getting Flindered.” 63 Flinders St., second floor; 61-2/9332-3180; dinner for two $50.

Pigeon Coffee: No other place gives you a feel for Surry Hills’ transformation like this quirky café, where Sydney’s creative types gather to while the day away. Green Astroturf covers one wall, a pigeon silhouette hacked out of it, and what looks like an abstract sculpture hangs on another—upon closer inspection, it’s just old milk lids nailed to plywood by the resourceful owner. Off-kilter it may be, but this spot whips up killer takeout coffee using a dozen or so varieties from across the globe. Building 2/431 Bourke St., Shop 3; no phone; coffee and pastries for two $10.

Shady Pines Saloon: Looking for a honky-tonk bar in Sydney? Shady Pines fills the bill. A giant longhorn steer head juts out from the wall and Willie Nelson plays the sound track at the spaghetti-western-style lounge, ironically named after the retirement home where Sophia lived on The Golden Girls. Saddle up to the counter or slide into a booth and order a boilermaker (a pint of beer and shot of whiskey). 256 Crown St., Shop 4; no phone; drinks for two $15.

Table For 20 & Sticky Bar: Don’t forget to bring your cell phone to this attic bar hidden on a side alley: the only way to get in is by texting the friendly bouncer, who keeps his number taped to the door. Bartender Michael Fantuz pays homage to his Venetian roots with Italian-inspired cocktails such as the Lovegun, a mix of amaretto, Campari, and orange juice, and the Hendrick’s Mist (Hendrick’s gin, house-made lemon syrup, and a splash of limoncello). 182 Campbell St., second floor; 61-416/096-916; drinks for two $38.

Belvoir Street Theatre: A-list actors Cate Blanchett, Geoffrey Rush, and Judy Davis are all alums of this prestigious 25-year-old theater, outfitted with a 330-seat main stage and an underground 88-seat experimental space. Catch a show here and you’ll likely spot as many boldface names in the audience as onstage. 25 Belvoir St.; 61-2/9699-3444.

Collect at Object Gallery: An exhibition space dedicated to shows about forward-thinking design make up the top floor of this spacious gallery that’s housed in the converted chapel of the Modernist St. Margaret’s Hospital complex. Just below, there’s a trendy boutique selling homegrown trinkets, from quirky jewelry to mod housewares in china, glass, and acrylic. 417 Bourke St.; 61-2/9361-4511.

Flinders Street Gallery: Set on the eastern fringe of Surry Hills, owner Jason Martin’s whitewashed gallery is filled with pieces by international artists that range from traditional acrylic paintings to cutting-edge sculptures made with horsehair and Laminex. Don’t miss Tom Langlands’s color-block canvases, reminiscent of digital-era Rothkos. 61 Flinders St.; 61-2/9380-5663.

Friends of Leon Gallery: Wunderkind set and costume designer Leon Krasenstein is not yet 30, but has already logged extensive stints with the Australian ballet and opera, and just opened this contemporary gallery on a quiet residential corner. On view: works by emerging Sydney talent (mostly female) that is both affordable and accessible. 82 Marlborough St.; 61-4/0324-8978.

Great Value Adina on Crown The best option in Surry Hills, Adina may not look like much from the outside, but its modern one- and-two-bedroom apartments are spacious and functional, with kitchens and four-top dining tables. There’s also an outdoor pool and barbecue pit shaded by palm trees. 359 Crown St.; 61-2/8302-1000; doubles from $235.

Great Value Kirketon: Retro glamour is the theme at this 40-room hotel in edgy Darlinghurst, just north of Surry Hills. Marble terrazzo floors, leather banquettes, and glass walls make up the groovy lobby, while guest rooms are outfitted with mohair throws and low-lit, Art Deco–style lamps. The hotel is a bolt-hole for night owls, who gather at the ground-floor Eau de Vie cocktail lounge to be served by the city’s savviest barkeeps. 229 Darlinghurst Rd.; 61-2/9332-2011; doubles from $145.

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