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By The Way
Detours with locals. Travel tips you can trust.
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Wendy's Secret Garden.
Wendy's Secret Garden.
CITY GUIDE

A local’s guide to Sydney

Wendy's Secret Garden.
Wendy's Secret Garden.
  • By Riley Wilson
  • Photos by Brook Mitchell
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Sydney is the emerald jewel in the crown of Oz, a sparkling, seaside city that works hard and plays harder. It’s in a period of substantial growth, with commercial and residential development battling with the cultural and historical backbone of a city known globally for its art, design, food, flair and beaches.

Despite the rising cost of living, Sydney — home of the indigenous Eora nation — is exceedingly accessible: botanical gardens, cliffside walks and white-sand beaches are open year-round, and keeping the calendar going is a calendar of free festivals — celebrating everything from single-origin coffee and local film to the LGBT community and huge light displays. We can sometimes take ourselves too seriously and forget that we live in a place that celebrates social diversity, good food, coastal swells and pub culture with almost the same reverence. But don’t get us started on the transport delays.

Meet Riley Wilson

Riley is a native Sydneysider who grew up between Australia and America, with extensive travels throughout Europe and Asia along the way. She’s a journalist and a lover of beach volleyball, roller-skates, olives and tea.

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IN THE ACTION
Chippendale
Significant investment has been made in Chippendale, outfitting an industrial area formerly home to workers’ cottages and sites into an urban destination, replete with an upmarket boutique hotel (the Old Clare) and a winding network of by-foot-only locales. Contemporary art space White Rabbit Gallery is within walking distance; Kensington Street is home to Spice Alley, with hawker-style offerings from a variety of Southeast Asian vendors. There are plenty of Airbnbs in the area, as well as backpacker hostels, big-name hotels and serviced apartments. Find the neighborhood.
LOW-KEY
Potts Point
Behind the bright lights of Kings Cross, closer to the water, things quiet down a bit. Strip clubs and all-night pubs are swapped out for boutique hotels in old mansions, 10-seater coffee shops and a bookstore (Potts Point Bookshop) that caters to the bibliophile. Potts Point — and neighboring Elizabeth Bay — balance nature and the built environment, with Art Deco apartments nestled among London Plane trees, marinas, excellent eateries and youth hostels. It’s a cosmopolitan residential pocket, with a great local theater and plenty of heritage-listed buildings. Find the neighborhood.
Neighborhoods

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Eat

BREAKFAST
Flour and Stone
Nadine Ingram has created a bastion for the pastry devoted, and the overflowing shelves of tarts, cakes — sliced and whole — lamingtons, sandwiches and pies are proof of that. Pair a ham-and-gruyere sandwich or eggs on toast with a pot of Grey Rabbit from local company Rabbit Hole tea and whittle away the morning.
BTW: Your eyes are not bigger than your belly. The extra chocolate-hazelnut cake will fit. Or, at least, it’ll fit in your bag. The lamington, too. And the madeleine.
Flour and Stone, 53 Riley St. Woolloomooloo NSW 2011, Australia
BREAKFAST
Sweet stall at Thanon Khaosan
It’s all about the curb appeal at this Thaitown favorite — join the queue in front of the fairy-lit cart perched on the busy pavement that’s stacked high with a massive variety of Thai sweets. Sticky rice and mango comes with a pouch of salty coconut cream to pour on top. Order a hot (or cold) Thai tea to go, and head to Hyde Park to lie down after the sugar rush.
BTW: Depending on the day, certain treats come out later than others. It opens around 10:30 a.m.
Sweet stall at Thanon Khaosan, 413 Pitt St. Haymarket NSW 2000, Australia
LUNCH
Third Rail Cafe
Unassuming? Yes. Bustling? Absolutely. Just a few minutes north of the Harbour Bridge, this local favorite outside Waverton train station is a standout every day of the week. The coffee, by Sydney roaster St. Dreux, is expertly handled; baristas turn out latte-art swans, deers and leaves atop flat whites and piccolos. Generous portions of poached eggs on avocado bruschetta, or spicy chicken burgers with thick-cut chips, will have you set for a day exploring any number of the bush tracks or parks in the greater Waverton area.
BTW: The action is close by: The Coal Loader, a former industrial site, is now a huge community garden with stunning water views.
Third Rail Cafe, 4/100 Bay Rd, Waverton NSW 2060, Australia
LUNCH
Harry’s Cafe de Wheels
This spot is a stalwart for sailors (the navy base is next door), theater patrons and locals alike. It’s the site of the original Harry’s pie caravan, which Harry Edwards opened in 1938 before heading to war. He reopened it in 1945, and it has been continuously running since. These days, the pies are a little pricier, but the peas are still mushy, and the gravy is still hot.
BTW: Ask for a chicken Tiger (a chicken pie, stacked high with mashed potatoes, smashed peas and gravy). Look out for the seagulls.
Harry’s Cafe de Wheels, Cowper Wharf Road and Dowling Street Woolloomooloo NSW 2011, Australia
DINNER
Kindred
Kindred — homey, warm, with soft lighting and three sets of stairs — is packed with locals regardless of the night. They return for the daily housemade pastas (loopy, thick bucatini; folds of pappardelle) and velvety chicken liver parfait. It’s hard to go wrong: even side salads and the house sourdough are knockouts. The waitstaff is extremely nimble and kind, and they often wear combat boots.
BTW: You’ll need to book in advance for dinner here; ask for a table overlooking the first floor, so you can watch all the action.
Kindred, 137 Cleveland St. Darlington NSW 2008, Australia
DINNER
Bart Jr.
A meal at Bart Jr. is the party you were invited to all along. Sit among this creative crowd of Sydney’s quirky characters while devouring kingfish crudo with teeny, bursting pomegranate seeds or homemade focaccia lathered in fermented, flavorful chili butter. You can easily whittle away the evening here, leaned up against exposed brick walls beneath twinkling fairy lights, with any of the Australian tipples or deliriously pretty cocktails in hand.
BTW: Consider the snacks. A fritter or a bowl of fat Sicilian olives will not ruin your appetite, I promise.
Bart Jr., 92 Pitt St, Redfern NSW 2016, Australia
LATE-NIGHT
The Barber Shop
In 2014, Sydney’s nightlife shifted in part because of “lock-out” legislation, tightening restrictions on bars and flexibility for night owls. The Barber Shop has weathered the storm. During the day, the barber delivers beard trims, haircuts and shaves. At night, behind the back door, it’s all velvet cushions and candlelit gin and tonics, with mustachioed bartenders divining cocktails with 750 gins from around Australia and the world.
BTW: If it’s too busy, pop across the alley to the Baxter Inn, down to the Rocks for the tiny Bulletin Place, or across to Darlinghurst for Shady Pines Saloon.
The Barber Shop, 89 York St. Sydney NSW 2000, Australia
LATE-NIGHT
Yellow
The dinner service here is divine, but you’ll come back for the desserts. Yellow is notably vegetarian- and vegan-friendly, having transitioned to a meat-free menu in 2016. Quenelles of eccentric sorbets, curds and granitas are topped with seasonal fruits, shards of meringue and any combination of earthly delights. The restaurant closes at 11 p.m., so pop by to sweeten the evening.
BTW: Come back on the weekend for brunch, which offers experimental breakfast foods — paired with wines or juices.
Yellow, 57 MacLeay St. Potts Point NSW 2011, Australia
(Sydney illustrator Jess Cruickshank for The Washington Post)
LOCALS THINK YOU SHOULD KNOW
  1. Public transport can get packed; if you’re not sure what you’re doing, seek out someone in orange at train stations who can help you — or ask a fellow commuter. We’re more than happy to help.
  2. The Opera House is iconic, and plenty of visitors take a tour of the space. Don’t. Make time to see a show instead and experience the venue as it’s meant to be enjoyed: as a performance space.
  3. If you’re going to drink as much coffee as the locals do, consider investing in a KeepCup, an Australian-designed and -made reusable coffee cup. You’ll get discounts at certain cafes for helping the environment.
(Sydney illustrator Jess Cruickshank for The Washington Post)

Do

Ensemble Theatre
Founded in 1958, Sydney’s longest continuously running independent theater remains a powerhouse for intimate performances. The theater company incubates new Australian works as well as established international favorites, with regular premieres often leading to celebrated seasons. The physical theater itself is small, and, after the stage show is over, the expansive waterfront view (enjoyed from the bistro downstairs) will put on an encore.
BTW: Arrive early so that you can check out the view from the bar in the foyer.
Ensemble Theatre, 78 McDougall St. Kirribilli NSW 2061, Australia
Dinosaur Designs
Louise Olsen and Stephen Ormandy started this resin-based jewelry and homewares brand in 1985, and they have since expanded to stores across the country and to boutiques in London and New York. The pieces represent a quintessentially Australian design ethos — quirky, forward-thinking, with deference to nature — and make for fantastic keepsakes and gifts. The resin collections are all designed and handmade in Sydney.
BTW: While the Paddington shop is glorious, the Redfern location houses last season’s stock and discontinued and imperfect pieces. Find a bargain there.
Dinosaur Designs, 339 Oxford St. Paddington NSW 2021, Australia
Wayward Brewing
Wayward is a star on the inner-west beer circuit. The locally owned brewery describes itself as being inspired by the road less traveled, so the variety of brews is a global journey. There are 24 taps (including guest taps to support other independent breweries), as well as refillable takeaway growlers. A favorite is the sour, punchy raspberry berliner weisse, which sits pretty and pink in a schooner or packaged up in an artfully designed can, or “tinnie.”
BTW: The brewery runs tours on the weekends ($25 per person), but book in advance to make sure they can make numbers (minimum three people).
Wayward Brewing, 1 Gehrig Lane Camperdown NSW 2050, Australia
Wendy’s Secret Garden
Wendy Whiteley — former wife and muse of the late Australian artist Brett Whiteley — has created a wonderland Alice would be jealous of, right on the lip of Sydney Harbour. A five-minute walk from Milson’s Point train station, this patch of green is particularly special for the mazelike paths and the collection of trinkets among native plants and flowers.
BTW: Continue down to the waterfront, where there’s an epic view of the bridge.
Wendy’s Secret Garden, Lavender St, Lavender Bay NSW 2060, Australia
Bronte Beach
Most visitors make a beeline for Bondi and the photogenic Icebergs Pool. Check out Bronte instead, two beaches south. A park next to the beach has picnic tables, and there’s a free-to-use ocean pool at the right of the beach. When you’re done in the suds, or before you even make your way to the sand, stop in at the Bogey Hole Cafe. Locally famous Iggy’s Bread is used in the sandwiches, and the mango-and-banana smoothies are thick and tangy.
BTW: This beach is patrolled most days, but always swim between the flags; the currents and wave conditions can change very quickly.
Bronte Beach, Bronte NSW 2024, Australia
Dawes Point Reserve
On the edge of the harbor, this park at the northern part of The Rocks is best enjoyed by taking a seat on the grass as the sun sets, with the beer-fueled banter from the Harbour View Hotel audible and the Sydney Harbour Bridge climbers finishing their excursions above you. Dawes Point was one of the colony’s first fortification sites in Sydney Cove and the site of the first recorded contact between the Eora, the Aboriginal Australians in the area, and Europeans.
BTW: The Opera House is east of the Harbour Bridge, so bring your camera.
Dawes Point Reserve, Hickson Road, The Rocks
Henry Deane Bar
You’d be hard-pressed to find a view as smashing as this for the price of a drink. Henry Deane — the cocktail lounge at the Hotel Palisade, which was renovated from its days as a hotel for wharf workers and reopened in 2015, with interior design by Sibella Court — features plush pink couches, moody wallpaper and brass details matched only by that view out the double-hung window and the arty cocktail in your hand.
BTW: Snag a seat on the balcony, overlooking Sydney’s pride and joy.
Henry Deane Bar, 35 Bettington St. Millers Point NSW 2000, Australia
Riley Wilson
Riley is a native Sydneysider who grew up between Australia and America, with extensive travels throughout Europe and Asia along the way. She’s a journalist and a lover of beach volleyball, roller-skates, olives and tea.
Brook Mitchell
Brook Mitchell is a contributing photographer to The Washington Post based in Sydney.

CITY GUIDES