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The brick-and-iron warehouses of the old Eveleigh Railway Workshops host a diverse lineup of experimental music, theater, film, and fine art. Located on the border of Redfern and Waterloo, Carriageworks was restored to keep the historical roots intact while providing a space for cutting-edge culture. Every Saturday, more than 70 stalls fill the former railyard outside with organic produce, artisan breads, specialty coffee, and exotic flowers as well as street food from the likes of chef Kylie Kwong during the farmers’ market. Fuel up at the market and then get inspired by whatever is on display inside this artist-run venue. Big annual events for Sydney Contemporary, Pacific Runway, Sydney Gay and Lesbian Mardi Gras, and the Sydney Festival are also held here throughout the year.

The cornerstone of the Kensington Street Precinct, at the heart of the funky Chippendale neighborhood, the Old Clare is the storied pub she used to be and so much more. Tonkin Zulaikha Greer Architects built a glass-and-steel walkway between the former Clare Hotel and the neighboring Carlton United Brewery building, both dating to the early 20th century, to create a 62-room boutique hotel that simultaneously feels historic and edgy. Original wood panels and brick walls blend seamlessly into spotted gum floors and nude-colored walls, exemplifying the creative reuse that pervades the Chippendale suburb, an inner-city district of galleries and cafés situated at the crossroads of Glebe, Redfern, Surry Hills, Chinatown, and the Central Business District. The design echoes other landmark Sydney restorations by Tonkin Zulaikha Greer such as the Paddington Reservoir Gardens and Carriageworks, an arts complex located just down the road. The Old Clare also brings two more standout restaurants to Chippendale, including the first Australian venture by Michelin-starred British chef Jason Atherton. Whether guests soak in the egg-shaped tub in their loft room, take a sunrise yoga class on the rooftop pool deck, or sip a “Ginny Hendricks,” a watermelon-dill concoction with bitters and Hendrick’s gin, at the midcentury-modern bar, they’ll have a story to tell. The Old Clare is a tale that keeps getting better.

Formerly Blue Sydney.

Carefully constructed around support beams and pipes from a 100-year-old wheat and wool wharf, this hotel offers a beautiful mix of old and new that juts out into the Woolloomooloo harbor. The Heritage Level is where you’ll find original wooden pier pilings, metal wheels, and conveyor belts that date to 1910, but classic touches such as early-20th-century photographs of Sydney are scattered throughout the property. Goose down bedding, plush furnishings, walk-in showers, and in-room iPads make modern travelers feel right at home, and the bar that runs the length of the central atrium—hanging Swarovski crystals shine pink and purple in the evening candlelight—often hosts fashion shows and cocktail events. Most rooms have sliding glass doors that take advantage of the hotel’s over-water location between the Royal Botanic Gardens and Rushcutters Bay; they open to either the city skyline or the Potts Point naval base. Maritime history buffs should book the latter and check out the site on the wharf from which sailors boarded ships for Gallipoli.

Founder’s Note: Uncommon Travels

Opened in time for the 2000 Sydney Olympics, the Establishment is a pioneering 31-room boutique hotel housed in an 1890s steel plant near the modern-day stock exchange building downtown. Managed by the hospitality group Merivale—which started as a fashion house specializing in fascinator hats and mini skirts—the hotel is popular among brand executives who book the 328-square-foot Loft Penthouse for product launches and photo shoots. Rooms feature wood furnishings, swinging metal doors, animal hides, and suedelike daybeds as well as such amenities as Apple TV, Bose surround sound, and Lululemon yoga mats. Bathrooms are particularly luxurious here, with marble floors, freestanding tubs, Bulgari products, and tall windows that open up to Sydney’s bustling business district. The best part about the Establishment, though, is the internal access it offers to some of the city’s hottest bars and restaurants, which are housed within the same complex as the hotel. And after enjoying live music and a few stiff cocktails at the speakeasy Palmer & Co, guests are welcomed to bed with Sleep Tight tea and a homemade chocolate chip cookie.

Towering over the tin roofs of the historic Rocks district, the Shangri-La Hotel has helped set the standard for Sydney hospitality, not to mention harbor views. Alongside the Asian influences, personal attention, and secret scent (it’s not just the cascading floral arrangements) that Shangri-La is known for, the Sydney hotel also incorporates earthen Aussie tones and a host of foodie surprises—ranging from an award-winning deconstructed carrot cake to a 36th-floor restaurant with 360-degree, floor-to-ceiling vistas. In 2014, all the premium suites and the Horizon Club Lounge were spruced up with pops of turquoise to complement the color palette of cream, gold, and dark wood. Behind the scenes, the Shangri-La has worked hard to become more sustainable and socially conscious; initiatives include adding energy-efficient and water-saving fixtures, producing much of its food in-house, and donating money to local charities such as OzHarvest.

Named for the wife of Governor Lachlan Macquarie, who presided over New South Wales in the early 1800s, this site provides one of the most spectacular views in town. Find the historic carved-rock ledge in the Royal Botanic Garden, east of the Opera House, where you’ll drink in a vista encompassing the Bridge, harbor and distant mountains, along with historic sites like Kirribilli House (the prime minister’s residence), the island of Fort Denison and the Navy Dockyards at Woolloomooloo.

Find cool pieces by an array of new and noteworthy Australian brands at this small concept store, founded to showcase independent designers in an artistic shopping environment. The Melbourne space stocks a monthly edit of men’s, women’s, and children’s clothing, with original and limited-edition pieces by around 100 local lines. With so many unique options on offer, you’ve got an excellent chance of finding something that perfectly suits your aesthetic, be it a little black dress by Ella Fashion, or attention-grabbing earrings by Plain Janes. If you can’t find what you’re looking for downtown, you can always check out the other Design a Space locations in Fitzroy and Windsor—the selection is different at each store.

For a glimpse of Sydney‘s high society, visit Vaucluse House, a beautiful villa and garden in the Eastern Suburbs near Watsons Bay. A gothic revival mansion built in 1803, Vaucluse House once belonged to ex-convict Sir Henry Browne Hayes, who was shipped to Australia from England for abducting a banker’s daughter. Some punishment. The mansion also served as the home of writer, explorer, and local dignitary William Charles Wentworth. Once you’re done eyeing the antiques and memorabilia, check out the tropical gardens and settle in for a cup of English breakfast and a warm scone at the well-appointed tearoom. There’s also Milk Beach and the Hermitage Foreshore Track nearby, a gorgeous coastal walk for those looking for a little more adventure.

The craft cookies, cakes, and ice cream churned daily here from local milk and fruit are as creative as they come. Ask for a nostalgic Australian treat, and you might be offered a Mit Mat (a ganache-filled play on the Tim Tam), a Ro-Vo (a room-temperature spin-off of an iced VoVo), or a Jatz pie (like a caramel slice topped with a mosaic of Arnott’s Jatz crackers). The bloke behind the brilliance is none other than Alistair Wise, son of cookbook author Sally Wise, who spent a stint working with Gordon Ramsay. This emporium of happiness—and envy, to be sure—also whips up scrumptious savories including a mean scallop pie and a buttery poached chicken “sanger” with bacon, lettuce, hummus, mayo, and hard-boiled egg.

Over the past 15 years, Wendy Whiteley (known as the “goddess muse” and wife of one of Australia‘s most famous artists, Brett Whiteley) has lovingly restored a once derelict piece of land, owned by the NSW Rail Corporation. It’s a magical place to reflect, talk or read and to simply get away from the city’s noise. The views are spectacular. About 5-10 mins stroll from Luna Park. http://en.wikipedia.org/wiki/Wendy_Whiteley#Wendy.27s_Secret_Garden This site was visited during AFAR Experiences, May 6-9, 2013: http://www.afarexperiences.com/

This bite-size coffee stand in the Victorian-era Strand Arcade building downtown is perfect for a midday lift. Run by the team behind Coffee Alchemy in Marrickville, Gumption serves coffee and only coffee (no food). Six single-origin bean varieties are on offer, three of them filtered hot, the other three dripped cold and served over ice. Don’t think about asking for milk, though, unless you mean a steamed drink. They’ll deny you. The staff is not snobby, just matter-of-fact. The coffees come small and extremely drinkable—even for dairy lovers.

On the first Saturday of the month, locals shop for vintage apparel and antique home decor at this flea market.

This two-level Cantonese palace—connected by an escalator—is lined with tanks of live fish, crustaceans, and bivalves, which the staff will stir-fry, steam, salt-and-pepper, and douse in XO sauce to your heart’s delight. There are many reasons the Chinatown establishment is beloved among in-the-know locals and hospitality veterans, and they extend from the warm, welcoming service all the way through the exquisite live abalone sashimi, mud crab hot pot, and private reserve range of wines. For a Chinese food adventure, arrive late (this place is open until 4 a.m.) and order straight from the live tanks. At least, that’s what the rock stars, politicians, and CBD chefs just getting off work do.

The Carrington’s long and rich history spans nearly 125 years since her opening by Sydney hotelier Harry Rowell. Originally named The Great Western, this Grand Old Lady soon became a popular retreat for international guests, Sydney’s elite, and adventurers eager to explore the Blue Mountains’ natural wonders. The hotel is steeped in history, tales of adventures and royalty, and perhaps even a ghost tale or two. The walls are covered with vintage photographs and the place looks like it was sealed in a time capsule (and yet still boasts modern amenities like wifi). The hotel bar is vintage, perfect for a glass of wine or local pint after a long day of adventures in the Blues. There are function rooms, a pool table, an elegant dining room (plus a more casual dining establishment, which used to be the town bank, on the property, as well as a stand-alone pub), as well as a 100-year old regulation snooker table. An onsite bottle shop is available, offering a wide variety of gourmet foods and excellent beers and wines, and a brewpub is even in the works.