Sydney got off to a rough start. The city, named after the British baron who authorized the establishment of a penal colony here in 1788, was inhabited mostly by convicts in its early days—a fact that’s still the subject of many Australian jokes. Even so, there was no doubting the splendor of its surroundings.
Upon entering Sydney Cove, Arthur Phillip, the first governor of New South Wales, called it “the finest harbour in all the world,” and whether you’re looking down on the sailboat-dotted bights from the top of Harbour Bridge or gliding across the water on a ferry, you’d be hard-pressed to argue. You’ll also find a city that has blossomed into a cosmopolitan, multicultural metropolis, home to 4 million of the world’s most open-minded and friendly—not to mention good-looking—people. The novelist Howard Jacobson once wrote that Sydney “flaunted its beauty, so can it be all my fault that I fell for it?” After just one glance, you’ll do the same.
Day 1
Harbor views from the top of the bridge and the inside of the opera house
The Sydney Harbour Bridge climbs to a peak of 440 feet above the glistening water, but for the adventurous souls who dare to scale one of the world’s tallest steel arch bridges—known affectionately to Sydneysiders as The Coathanger—the scary part comes much earlier.
Truth be told, I’m a wreck the entire morning leading up to my scheduled climb. I have to give myself a pep talk before I crawl out of bed at my city center hotel, the QT Sydney, and the tension rises as I sit through breakfast at The Grounds of the City, an Art Deco–inspired restaurant around the corner on bustling George Street, across from the stately Queen Victoria Building. I’m too full of butterflies to be hungry, but I’ll need fuel for the climb, so I wolf down a king crab omelet and a flat white (an Aussie latte). I briefly toy with the idea of ordering a nerve-steeling cocktail but decide it might not be a good idea.
It turns out I’m right, because BridgeClimb breathalyzes all of its clients before each ascent. I soon find out why. The first part of the climb is actually a tottering trek across a narrow catwalk, 160 feet above the shore. “It’s a bit daunting, but it’s not that hard,” says my charming climb leader, Amanda. She also notes that an Irish worker fell from this height during construction in the 1920s. He survived, breaking just three ribs, but even clipped to a steel safety cable, I am far from comforted.
Once our group has made it across the catwalk, things get less terrifying. We climb four ladders, then trudge up the bridge’s gentle arch. The three-and-a-half-hour climb involves 1,390 steps, and I’m glad I had that omelet by the time I reach the top. I’m also thankful that I faced my fears, because the view is astonishing. Early morning clouds have given way to bright sun, and the view stretches from the top of Hornby Lighthouse at the harbor entrance all the way out to Olympic Park (site of the 2000 Games), 10 miles to the west. The sailboat-inspired Sydney Opera House, a sight so surreal yet so familiar, is behind me. Skyscrapers sprout to the north and south. Eight lanes of morning traffic crawl along the roadway below. It’s enough to make me want to do that “king of the world!” thing from Titanic. I can neither confirm nor deny that Amanda snapped a photo of me doing just that.
I could stay up here forever, but there’s another party coming up, so down we go. The bridge lands in Sydney’s oldest neighborhood, the Rocks. Here, I meet a Tours by Locals guide named Lyndal, who tells me the area’s sobriquet dates from the arrival of the British, who settled where they found fresh water flowing into the harbor. “They sailed right into what we now call Circular Quay,” says Lyndal, a playful former flight attendant, “and on arrival, Captain Phillip said, ‘Military: take the stream. Convicts: to the rocks.’”
The view makes me want to do that ‘king of the world!’ thing from Titanic.
From here, Lyndal leads me past the 1841 Lord Nelson Brewery Hotel, home to Australia’s oldest brewpub, and on to the Big Dig, an excavation site where archaeologists have uncovered the foundations of more than 30 homes and shops dating from the settlement’s early days. Some of the artifacts recovered here have amusing stories, such as the porcelain fragments found in Cribbs Lane, discarded by the scorned mistress of a 19th-century philanderer. As Lyndal tells it: “She crashed all her china down the well.”
We continue past the Susannah Place Museum, a preserved set of squat brick rowhouses built in 1844, and conclude the tour at First Impressions, a three-sided sandstone sculpture that depicts the convicts, soldiers, and settlers who originally came here. “I always thought I’d go home to Queensland,” Lyndal says, surely echoing the thoughts of some of those early immigrants, “but this city has just seduced me.”
For lunch, I head into nearby Barangaroo, a harborside neighborhood of towering real estate developments (a massive casino is on the way) and green space. I take a waterfront seat at Cirrus, a new restaurant from Brent Savage, who has been a Chef of the Year in the Good Food Guide (Australia’s equivalent to the Michelin guide). The focus here is on sustainable, local seafood, and I fill up on New South Wales oysters, scallop sashimi, swordfish crudo, and fantastic grilled marron (a crustacean somewhere between a lobster and a crayfish in size).
Fighting through a seafood coma, I walk a couple of blocks north to the Barangaroo Reserve. Here, I meet Tim Gray, an Aboriginal Visitors Services guide who’s taking me even farther back into Sydney’s history with a culture tour dedicated to the area’s original inhabitants. Australia’s relationship with its indigenous people is fraught, to say the least, but the reserve—named after a female Aboriginal leader whom Gray refers to as “our first freedom fighter”—was created both to honor them and to educate the present-day populace about their lives. Gray leads me along a reconstructed sandstone coastline. On our left, waves lap against the rocks; on our right rises a terraced hillside thick with greenery (the park is home to 83 native species of trees and shrubs).
“We chose native plants to show how the Aboriginal people lived, utilizing plants for food, shelter, and medicine,” Gray says. “You can still use them today. The whole of Sydney, with all these plants, is a big pharmaceutical warehouse.” He plucks a Port Jackson fig off a tree and hands it to me. Tasty!
I lean on a rail to watch white-sailed catamarans skim across the water.
Next to the water, Gray points out a large block of sandstone bearing an inscription that looks like the number 101—a recreated Aboriginal carving. Holding his iPad over the stone, he shows me an interactive video of a tribal elder doing the carving. We climb a small hill, schoolchildren rolling in the opposite direction, and stop at a stand of trees, where Gray crushes leaves together to create a paste that kangaroo hunters used to cover their scent. Finally, he breaks out two different kinds of boomerang and explains how they were used for hunting. Do I want to throw one of them? Yes. Do I ask? No.
I thank Gray for the tour and make the short walk back through the Rocks to Circular Quay. The tourist-packed promenade here, which feels a bit like Barcelona’s La Rambla without the seediness, takes me along the wharf, where the city’s ferry boats decamp for the distant reaches of the harbor, and then around to the opera house, where I stop and lean on a rail to watch white-sailed catamarans skim across the water.
For dinner, I only have to climb the steps of the opera house. Bennelong, named after an 18th-century Aboriginal leader (Barangaroo’s husband, actually), may have the most beautiful dining room in the world. I sit at a sloping glass window, beneath a vaulted wooden ceiling that makes me feel as if I’m Jonah and I’ve just been swallowed by the whale. Outside, the sun sinks behind the bridge and the city lights up, but chef Peter Gilmore’s contemporary Australian cuisine refuses to be upstaged by the view. I have Fraser Island spanner crab in a crème-fraîche emulsion, paired with a New South Wales chardonnay; a whole roasted John Dory served on the bone with a Victoria gamay; and for dessert, a sour cherry jam lamington (a play on a traditional Australian cake).
Now that I’ve had some wine to wet my whistle, I’m ready for a real drink. I walk past the offices, shops, and pubs on George Street before ducking down an unassuming alley and into an unmarked doorway. Down the stairs I enter the Baxter Inn, Sydney’s premier whiskey bar; the bottles behind the bar are stacked so high that the white-aproned bartenders need ladders to fill their orders. The list leans toward Scotch, but I can’t totally shake my American predilections, so I have a Weller 12-year, a wheated bourbon that can be hard to find even in Kentucky.
Standing at the bar, I realize how much I’ve been on my feet today, so I trudge back to the QT Sydney. As the elevator doors close, James Brown blares over the speaker: “I feel good!” I do, too, but not as good as I will after I hit the sack.
Day 2
Getting to the heart of Sydney’s art scene
Sydneysiders have a different definition of “suburb” from the American one. The inner ’burbs here are less about white picket fences than about creativity and expression. They’re also close: Chippendale, the up-and-coming neighborhood I’m off to this morning, is a 10-minute cab ride south of the QT Sydney.
The space, the staff, the day—hell, this whole country—are
so sunny.
On Kensington Street, a pedestrian walkway lined with sparkling new bars and restaurants, I come to the sunny, open-air Concrete Jungle Café. I’m greeted by a pair of tanned and tattooed Aussie chaps, who razz me about my Golden State Warriors hat but quickly bring me a Moroccan mint tea and a Blue Majik Smoothie Bowl (a blend of coconut water, yogurt, blue algae, pineapple, and banana topped with blueberries and granola). Eating like this, I can see why everyone around here is so fit.
After breakfast, I stroll through Central Park, where vendors sell handicrafts—beach-towel sundresses seem especially Australian—and toddlers wet their feet in a staircase-like fountain. From here, I head down a tree-lined side street to the White Rabbit Gallery, a four-story space that houses one of the world’s largest collections of contemporary Chinese art. My favorites are both by Taipei-born Peng Hung-Chih: Farfur the Martyr, a sculpture of a crucifixion figure with a Mickey Mouse–style head, and Excerpts from the Analects of Confucius, a video installation in which a dog appears to be writing Chinese characters on a wall with its tongue. (The artist has reversed the film; the dog is actually licking the characters off.)
Lunch is around the corner at Ester, a contemporary Aussie restaurant (think California cuisine) that opened nearly five years ago and has since won pretty much every food award Sydney has to offer. “Oh, you’ve come a long way,” my waitress says when she learns I’m American. “Let’s get a drink in you.” (Bless the Aussies.) The tasting menu takes me through fermented potato bread with trout roe and kefir cream, a mini–blood sausage sandwich, wood-fired cauliflower with mint and almond, hanger steak, and some other dishes that come out in such frantic succession I don’t write them down. Radiohead and Joy Division play on the sound system, which seems odd given that the space, the blue-aproned staff, the day—hell, this whole country—are so sunny.
I need a walk after all that gustation, so I head over to the gritty, LGBT-friendly suburb of Surry Hills. I pass record shops and coffee houses on Crown Street before making a couple of turns down a twisty residential alleyway to Brett Whiteley Studio. Whitely, one of Australia’s great contemporary artists, opened a studio here in the 1980s, and it was preserved after his death from an overdose in 1992. The ground floor is scattered with his sculptures and paintings, including the Hieronymus Bosch–esque wall panel Alchemy and nudes that could have come from a twisted Modigliani. (“Apparently he really liked women, beer, and sharks,” I overhear a fellow patron saying.) Upstairs is Whiteley’s studio, complete with paint-spattered plywood floor and inspiration boards bearing images of Albert Einstein, Bob Dylan, and Andy Warhol’s Velvet Underground banana. I think I would have gotten along with this guy.
From here, it’s a short cab ride to the Art Gallery of New South Wales, on the edge of the Royal Botanic Garden. The building reminds me of a mullet: business in the front (with a Neoclassical portico), party in the back (a mish-mash of glassy modern extensions). The collection includes works by European masters such as Picasso and Bacon, as well as Asian and Australian artists. I’m particularly drawn to the large, dot-painted landscapes of the Aboriginal artist collective Papunya Tula.
Another cab takes me back to The Old Clare Hotel in Chippendale, where I’m having dinner at the acclaimed modern Australian restaurant Automata. Well-heeled Sydneysiders populate a communal table at the center of the room, which is lit by fixtures made from motorcycle parts. The five-course tasting menu includes delicate white asparagus in a miso sauce; garlicky prawns under a squid-ink-noodle blanket; smoked and grilled trout with turnip, daikon, and rhubarb; smoked lamb neck with charred eggplant; and a roasted grain parfait for dessert. The red rice sake that’s paired with the last dish is so delicious that I chase down my server, a redheaded Michigan expat named Abby, to double-check I have it spelled right: It’s a 2015 Ine Mankai from Kyoto’s Mukai Shuzo brewery.
I ask Abby where I should go for an after-dinner drink. She looks at the snap-button Western shirt I’m wearing and replies, “You’ll fit in at the Shady Pines Saloon.” Like the Baxter Inn, the Shady Pines is tucked in an alley, behind an unmarked door, down a flight of stairs (the two bars started Sydney’s “small bar” speakeasy trend). Inside, a raucous honky-tonk blues band plays for some shirtless tattooed guys under strings of Christmas lights and an insane—I mean completely insane—taxidermy menagerie: bull, bear, mountain goat, fox skunk, vulture, moose, a cobra dangling from the moose’s antlers. This must be what Australians think Nashville is like. I wish they were right, because the Shady Pines would be the best bar in Nashville.
Day 3
Bondi Beach Babylon
I’ve been in the country for two days now and still haven’t felt white sand between my toes—an oversight that needs to be remedied posthaste. Fortunately, it’s only a 20-minute cab ride east from the city center until I’m standing at the edge of Bondi Beach, one of the most famous oceanfronts in the world.
It’s a thing that you’re not supposed to go swimming on an empty stomach, right? No? Anyway, I opt for breakfast a couple of blocks up from the beach at Bills, a spacious restaurant filled with boho types tapping on laptops to the tune of Bill Withers’s “Lovely Day.” I grab a booth and tuck into a breakfast of poached eggs, gravlax, sourdough toast, tomatoes, and avocado, with a berry and coconut yogurt smoothie. The Aussies may be the only people in the world who like smoothies and avocados as much as I do.
Leaving Bills, I spot the endearingly named Gertrude & Alice Cafe Bookstore across the street, so I stop in and pick up a Peter Carey novel to read on the beach. Then I browse the shops on Hall Street and Campbell Parade for supplies, snagging some Billabong board shorts and Havaianas flip-flops at Surfection and a cheesy beach towel, printed with a kangaroo and a surfboard, at a beachside bodega.
No more delay: to the beach! I walk across the impossibly fine-grained sand, past the impossibly toned and tanned bodies (apparently we should all switch to the smoothie and avocado diet), to a spot where I can watch a Brazilian-style beach volleyball game (no hands!) on one side and kids in a surf school falling off waves on the other. The sky is flawless blue, the ideal backdrop for the prop plane doing barrel rolls over the beach. It’s less ideal for my New York–in–winter complexion, though. Do they make SPF 5,000?
Apparently, getting sunburned can work up an appetite, so I walk to the southern end of the beach and Bondi Icebergs. Perched on a rock outcrop, Icebergs is home to both a year-round swim club with an oceanside pool and a special-occasion restaurant. I take a window seat in the upstairs bistro, where I watch hardy old men do laps in the pool and surfers catch waves in the sea while I snack on bluefin tuna crudo, followed by Spring Bay mussels in a white wine, tomato, chili, and saffron sauce. I’m feeling so summery that I finish it off with an Aperol spritz.
Refueled, I swap my Havaianas for sneakers and head off on the nearly 4-mile Bondi to Coogee Coastal Walk. The trail takes me past sandstone walls carved by the waves into undulating forms straight from Dalí’s imagination; tide pools crusted with oyster shells; blufftop Waverley Cemetery, where gravestones overgrown with dandelions seem to reach out toward the sea; and Clovelly Bay, an inlet where divers take the plunge. I finish up with a dip at Coogee Beach. The swimmers here don’t wade out into the cold water so much as hurl themselves against it, and I follow suit. Brrr!
Once I’ve dried off—good thing I bought that kangaroo towel!—I cab to the QT Bondi a design-forward beach bum’s paradise where I take a nice long nap and an even nicer long shower. Cleaned up, dressed up, and not too sunburned, I hail another taxi and head into Paddington, a hip neighborhood between Bondi and the city center. I’m having dinner at Saint Peter, an award-winning “gill-to-tail” restaurant that experiments with offal and dry-aging—essentially treating fish like meat. The space is narrow, the lighting dim, but the seafood is as bright as the Bondi sun: fresh rock oysters, 13-day-aged broadbill tartare, beautiful sardine fillets in olive oil with a hunk of crusty bread, grilled mahi mahi. I enjoy it all with another spritz, not wanting to let go of the summer feeling.
I take a window seat at Bondi Icebergs and watch hardy old men do laps in the pool while surfers catch waves in the sea.
After dinner, I feel like a stroll, but I don’t make it far. Just a couple of blocks away is The Wine Library, perhaps the city’s best wine bar. I pull up a barstool and flip through the tome-like menu before asking the bartender, Andy, for help. He immediately pours me a glass from the bottle of French chenin blanc in his hand. As I take a sip, I notice a familiar song on the radio. “‘Waterfalls’?” I ask. Andy shrugs and smiles. “We decided to make it ’90s R&B night.” It’s like they knew I was coming.
And that’s the thing, I think, as I taste my way through the list. We may be all the way at the end of the world here, in a sun-kissed, intoxicating fantasyland, but the people make it feel like home. As if on cue, Andy offers me a shot of Fernet, a dram favored by many bartenders in my hometown, San Francisco. “The last Chinese emperor endorsed Fernet,” he tells me. “He said if you drink it, you’ll live forever, and it’ll make you a god.” He raises his glass: “So here’s to long life and becoming a god.”
I’ll drink to that.
Up Next: Three Perfect Days in Hawaii
