Get a taste of Sydney this summer with help from Mr & Mrs Smith and The Old Clare hotel in Chippendale. If this guide inspires you to take a well-earned trip, then enter our competition for a chance to win a £2,000 Get a Room! gift card to spend on a summer stay at over 1,000 Mr & Mrs Smith hotels. Enter now.
Where to stay
You can teach an old dog new tricks, according to The Old Clare, whose rooftop pool, destination restaurants, buzzy bar and handsome rooms occupy two heritage-listed buildings: a former student pub and what was once the Carlton & United Breweries' administrative HQ.
Nods to Clare's past have been lovingly preserved, including band posters, original fittings and the boozy boardroom, which was suspended in mid-air for six months while its surrounding structures were revamped.
The rooftop bar at The Old Clare is the place to be for cocktails and people watching when it's warm – swig a Dill or No Dill cocktail (an artful muddle of gin, cucumber, elderflower, smoked sea salt, lemon and dill) or a Frosé: rosé with watermelon and lemon.
Where to eat
The Old Clare boasts two incredible restaurants – the first is Kensington Street Social, where Brit-hit Jason Atherton (of Michelin-starred Pollen Street Social in London) devises dishes that fizz with invention. Be sure to try the English breakfast tea and toast – wild mushroom tea, gentleman's relish, bone marrow toast and wash it down with a Vegemite martini.
Automata, captained by home-grown talent Clayton Wells (ex-sous-chef at Momofuku Seiōbo), offers tasting menus designed with accomplished simplicity – expect local produce cooked with perfect restraint. The menu prompts plenty of 'cor, wossat?' moments: sugar-loaf cabbage with fermented mushroom, buckwheat and dried venison; grilled Wagyu tri-tip, aubergine purée and fermented pumpkin; Tarago River triple cream with pickled muntries, for example.
Even the Old Clare's minibars come with gourmet thrills a-go-go: Zokoko chocolates, beef jerky, Byron Bay Cookies, Thomas Chipman crisps, grapefruit fizzy pop and bottled cocktails await.
With so much temptation within, you'd be forgiven for wanting to stay put, but it's well worth the effort to venture outside. Chippendale has had something of a food renaissance in recent years, and you can find anything from Michelin-starred chefs to croissants worth queuing for, not to mention a deep fried Golden Gaytime ice cream. And yes, the latter is as wicked and delicious as it sounds.
Breakfast spots in Sydney
Worth the queue is Brickfields bakery, where you'll find great coffee, flaky croissants, lovely little cakes (the Persian Love cake is an excellent choice) and properly chewy sourdough bread. Something for Jess does well-made coffee using Five Senses beans and Toby's Estate roasts their beans out the back of their Chippendale set-up.
Put aside the bacon and egg roll and try something a little more interesting (no offence to the perfection that is the egg and bacon roll). At Glider KS the food has a Thai influence, which means dishes like matcha french toast, Thai omelettes and duck "brekky noodles" are on the menu, alongside more classic brunch dishes.
Best lunches in the city
Time to grab some friends, roll up your sleeves and hit up Spice Alley – a hawker-style lane that runs parallel to Kensington Street. Best to just let everybody choose their own meal and then nab a table. The roti and Chatterbox Chicken at Alex Lee Kitchen is a good bet, as is a bibimbap from Koa Kitchen and a tangle of noodles from Bang Luck Thai Street Food.
Sydney by night
Ester Restaurant on Meagher Street boasts show-off cooking and unshowy charm: order the hasselback spuds and the three milks dessert. Get your smoke on at LP's Quality Meats, a temple to barbecue on Chippen Street; the mashed potato with gravy is the stuff of dreams. A juicy cheeseburger at Ribs & Burgers is satisfying and a pizza from Andiamo Trattoria will hit the spot.
Or you could just hold out for dessert. Masterchef contestant Reynold Poernomo has created a fancy Willy Wonka-esque dessert bar in Koi. Expect treats like Bika, chocolate tapioca cake with tonka bean ice cream, yogurt and salted caramel and Moss, pistachio mousse, caramel gel, dulce cremeux, pistachio sponge, matcha moss, apple blossom jelly, nitro lime and yogurt and green apples.
Where to drink
Given that your base is a former pub, it would be rude not to honour Clare's brew-tastic past with a pot or schooner of beer at the Old Clare bar. But don't neglect Freda's on Regent Street, a fun speakeasy, with nifty little bar snacks to keep you going (think za'atar-dusted chicken wings with yoghurt), potent cocktails (the 50/50 Sazerac stars cognac, absinthe and bitters) and ear-arousing music nights. Craft beer-fiends should stroll to Glebe for Staves Brewery, which serves its own brews in its bar and beer garden. If it's a classic boozer you're after, The Lord Gladstone has a lovely beer garden, decent pub grub and is also responsible for that infamous deep fried Golden Gaytime – go on, you know you want to…
Places to go
Start with your near neighbours: art-lovers can gallery-hop from Tiny Tailor Gallery to White Rabbit Gallery (pause for dumplings at the on-site teahouse) to Harrington Street Gallery. Market-lovers can rummage around Brewery Yard, Carriageworks and Glebe Markets, a 15-minute stroll from Chippendale, while design-lovers can browse covetable furniture and furnishings at Cult on Levey Street and Chee Soon & Fitzgerald on Regent Street. All in all, it's the perfect place for all lovers to wander through alleys and narrow streets until you find something that tickles your fancy.
Further afield, seek out sociable Surry Hills, a 15-minute stroll away, to sip a flat white (or a cocktail). If food markets float your boat, look no further than Sydney Fish Market: admire the succulent seafood, and eat the most toothsome for lunch. Since you've come all this way to soak up some rays, head to Bondi Beach. It's not Sydney's prettiest stretch of sand, but it is the one on which to be seen.
If this has sparked your interest in a trip to Sydney, enter our competition for a chance to win a £2,000 Get a Room! gift card to spend on a summer stay at over 1,000 Mr & Mrs Smith hotels. Enter now.
Find more of Sydney's best restaurants on Deliveroo.
For more foodie inspiration, this time in the French city of love, read our city guide to Paris.