Comedian Tim Ross made Sydney his hometown more than 20 years ago. But memories of his first visit to the harbour city still cast a spell.
The best cities in the world make you feel like you’re a part of them
in an instant. They sweep you up and take you along for the ride
from the moment you arrive.
Sydney’s been my home for over twenty years, but it’s been under
my skin for as long as I can remember. I first arrived here after taking
the bus up from Melbourne with a bunch of university friends,
wanting to see the harbour city that had always loomed so large.
Our plan was to take in as much of the city as we could in our
short stay. But it was me that was taken. It’s a seductive town:
that Sydney weather, the light that sparkles, a surprise behind
every corner and cove and the people – all so damn beautiful.
I remember the sun as it dried the salt on my skin after my first
swim at Bondi Beach. I remember the views out of the bus window
as it chugged up that glorious hill on Bondi Road, the ocean behind
us and the city ahead.
I remember the pubs of Darlinghurst – their yellow tiles, cold
schooners and the spirited conversations with the new, if fleeting,
friends I found there – and the spices that swirled around Glebe
Point Road in the city’s inner west, calling us into one of the street’s
many Thai joints as we headed back to our hostel.
And I remember walking around Circular Quay and catching my
first glimpse of the Opera House, this city’s calling card to the world.
I still pinch myself, hardly believing I’ve been lucky enough to
You don’t have to be from a city to love that city. It only takes
one visit to Sydney and it will have a hold on you for life. Melbourne
will always be my home, but Sydney – a showoff and a hopeless
flirt – will always be my love.
The top 10 Sydney experiences to have now
1. See Watsons Bay minus the crowds
On a sunny weekend, Watsons Bay in Sydney’s east has a carnival-like atmosphere – kids racing through parks, swimmers plunging into the water at the local Baths, groups charging glasses in the beergarden of the suburb’s only pub, The Watsons Bay Boutique Hotel. But if you want to see it like the lucky ones who live here – as a quiet former fishing village with a patch of sand for every local – stay overnight at the hotel. Wake early to see the city skyline from your harbour-fronting suite, stroll past the dinghies lining the boardwalk on your way to Camp Cove for a morning dip, walk along the ocean cliffs of The Gap, then head back to the hotel before the day-trippers arrive for a breakfast of stuffed apple crepes or a classic bacon and egg roll (with a tomato compote twist).
2. Float in a hidden rockpool
A top 10 Sydney list without a secret place to swim? Impossible. But you’d be hard-pressed to find a spot more secret than Ivor Rowe Rockpool in South Coogee. It’s not a laps kind of pool – for that you’ll want Wylie’s Baths around a 15 minute walk north; this natural pool is better suited to waders and only 10 people are allowed to use it at any one time. Good thing so few know about it.
3. Book a table at Sydney’s most exclusive seafood restaurant
Josh Niland, who became the first Australian to win the world-renowned James Beard Book of the Year Award for his debut The Whole Fish Cookbook in May this year, has reopened Saint Peter restaurant in Sydney’s Paddington. The “fin to grill” seafood establishment, co-owned and operated with wife Julie, now features a long bar that runs the length of the skinny dining room and seats a maximum of 20 diners per sitting. Every dish here is listed with its provenance (that might be sea urchin from NSW’s Royal National Park or organic rock oysters from Wapegno) and served across the counter by Josh, Julie and their team. Don’t forget to order the anchovy-spiked coral trout with lashings of butter.
4. Sleep on an island just minutes from the city
Island life isn’t just for the sunny tropics. Cockatoo Island, just a short ferry ride from Circular Quay, is an easy break from the city (without actually leaving it). Once a meeting place for the Eora people, then a penal colony after European arrival, this UNESCO World Heritage site is as appealing for its history as its million-dollar location. And those who stay overnight can feel like it’s their own private isle come sunrise. There’s a campground with facilities but a more comfy stay can be found in one of the converted heritage buildings – inside you’ll find a fully-equipped kitchen, hot showers and, in some accommodations, a deck with barbecue so you can flip a steak with the famous bridge as your backdrop.
5. Climb one icon then dine at another
Combining two of the most exclusive views of Sydney Harbour – from the top of the Sydney Harbour Bridge and from a table at one of the city’s finest restaurants – Bridgeclimb’s Pinnacle experience offers dinner with one unforgettable show. After you’ve scaled the iron icon, you’ll be rewarded with the best seat in the house and a 6- or 8-course menu by chef Peter Gilmore at either his harbourside Quay or Bennelong restaurant.
6. Picnic by the harbour on Sydney’s Millionaire’s Row
Google ‘Duff Reserve’ in the eastern suburb of Point Piper, switch to satellite view, and there among the swimming pools, tennis courts and private jetties you’ll see a tiny park that’s as close to the harbour as you can get without getting wet. Located at the bottom of some steep steps off Wolseley Road, arguably Sydney’s luxest address, Duff Reserve delivers views to Sydney Harbour Bridge, Garden Island and even the sails of the Sydney Opera House. Bring a picnic hamper and rug, sit under the trees and watch the water shimmer as the boats sail by.
7. ‘Salut’ the city’s coolest wine bar
Chef Mat Lindsay shook up Sydney’s dining scene in 2013 with the launch of Ester restaurant in Chippendale. He went a step further in 2018 with wine bar Poly (get it? Poly-Ester), where the drinks menu is better described as a tome: expect everything from classic German rieslings to highly quaffable Australian pinot noirs, a huge selection of sakes, beers, ciders, cocktails, spirits, liqueurs and more. But a trip to this cosy-meets-industrial-cool Surry Hills bar is not just about finding liquid gold. Lindsay’s set menu with scallop crudo and sweet and sour pork neck is equally stellar for those who want to make a night of it.
8. Tunnel through a work of art
Even if you’ve never wondered what it would be like to walk through a giant tunnel made of 14,000 sheets of rice paper and 1800 pieces of featherweight bamboo, trust us, it’s worth finding out. Head to White Rabbit Gallery in Chippendale where The Ship of Time – an enormous sculpture by Zhu Jinshi – currently hangs off the ceiling by delicate threads. The installation is part of the And Now exhibition, which features 15 works across three floors and celebrates the first decade of the gallery.
9. Take your own wild things for a night at the zoo
The Roar and Snore experience at Sydney’s premier zoo (which includes accommodation in one of the glamping tents close to the animal enclosures) is world-renowned – and a family favourite. But if you want to turn up the luxe factor, book one of the rooms at the WIldlife Retreat, which opened in October 2019. Opt for one of the Animal View Rooms and you’ll find the zoo’s curious creatures literally hanging out on the branches right in front of your room.
10. Get lost down a laneway
The name doesn’t quite say it – Kensington Street in Sydney’s Chippendale is actually more of a precinct. Start at Clare Bar, decked out with vintage tiles and carpets and with a bar that glows like a stack of golden ice cubes, and order a glass of Louis Roederer or a pale ale from WA’s Fremantle. Then make your way to Olio for excellent Italian fare made using olive oil sourced from chef Lino Sauro’s family farm in Sicily. And find your nightcap at Gin Lane, where the menu of cocktails includes the must-have lemon Aspen gimlet – a delicious blend of Tanqueray London Dry Gin, Cointreau and lemon sorbet.