From crazy-good views to great things to 
chew, here are Time Out’s 25 things to tick 
off before you check out of town

Kayak at Pittwater


Just a 50-minute drive from the centre of town (off-peak), Pittwater is one of the Sydney’s most stunning bodies of water – all eucalypt-choked hills spilling down into calm, yacht-dotted water that stretches all the way up the northern peninsula. The best way to take it in is to hire a kayak and explore the bays and little beaches on the fringe of the waterway that hugs the Ku-ring-gai National Park. Make sure you stop for a spell on the beach at Scotland Island, Sydney’s only residential island, which sits in Pittwater just a little ways off Church Point. It’s tranquil, friendly, and you may just wind up looking at real estate brochures on your way out.

Prop up the Young Henrys tasting bar


Attached to the impressively industrial Young Henrys brewery in the graffitied back streets of Newtown – no, you haven’t taken a wrong turn, that’s it in that rough-lookin’ little cluster of brick joints – the YH tasting bar has a sharehouse vibe: tatty couches, crackly vinyl, lots of facial hair. Which is why we love it. Order up a tasting paddle of six YH brews – the guys will talk you through each one from the Real Ale to one of their special, limited-edition numbers – and settle in for 
a long afternoon.

Join the crush at Messina Darlinghurst


The lines get mammoth outside of this Darlo gelato institution, where punters pack in for scoops of Apple Pie, Poached Figs in Marsala and Gianduia (or something from the specials board that day). There are no real rules to the line – just don’t push in and you’ll eventually float through to the glass cases – and we say stick with the crowds afterwards and eat your cup or cone on the Victoria Street sidewalk. Not a fan of crowds? Try the branch at the Star.

Spend Saturday morning at Eveleigh 
Farmers’ Market


You’re probably not doing much cooking while you’re in town, but visiting the best farmers’ market in Sydney is still a must. Grab pancakes or a pork bun from celebrity chef Kylie Kwong’s stall for brekky, a slice of banana cake from Bird Cow Fish and a cup from Ritual Coffee and sit in the sun by the long, hipster-studded Carriageworks wall. We love all the musky smells of the Eumundi Smokehouse. Bring a camera if you like dogs: pugs in sweaters, poodles in booties… this is where they spend their Saturdays.

Sing a song at Lantern by Wagaya


You might not know this, but Sydney does good karaoke. Specifically, Chinatown does good karaoke – and Lantern by Wagaya is one of the best. There’s the novelty of having to go into a big city high-rise and up a lift to get there (it feels like you’re breaking in), and the rooms are creatively decked-out with easy-to-use touchscreen song-selection systems. But the best thing about Lantern is the food: order via the touchscreen menus near the door and gorge. You are the champion, my friend.

Raid the beer fridge at the Australian

The Rocks

There’s a big debate about which pub in the Rocks is truly the oldest – so let’s just say the Australian Heritage Hotel is one of the oldest, and certainly one of the best. Why? Well, it has that old-school Aussie pub charm and some very weird-ass pizza (crocodile), but our love affair has always been with the glass-doored beer fridge you’ll find behind the bar. Every shelf is labelled (‘wheat beer’, ‘pale ale’) and holds refreshing surprises like Victoria’s Two Birds golden ale and Tasmania’s Moo Brew. It’s like a tipsy little tour of the country – with your mouth.

Frolic in the Ladies’ baths at Coogee


This one’s for the women only, fellas. The natural sea bath is hidden behind a sheer bit of cliff face, where octopi, crabs and little fish commune with swimmers. It can get pretty rough in there depending on the time of year, but it’s a lovely secluded spot to take a book and flop out.

Stock up on chocs at Kakawa


The best chocolate shop in Sydney is a haven of hand-crafted chocolates, bags of honeycomb (covered in chocolate) and all manner of other sweet treats. You’ll want to take a full wallet for this one. It may not be cheap, but the quality is excellent, and all made in-store.

Explore Cabramatta


Discovering this rich and colourful suburb is as easy as hopping a train (try the Inner West & South and Bankstown lines). Once you’re there, you’ll immediately be immersed in Sydney’s biggest Vietnamese community. Picking a restaurant can be a matter of just closing your eyes and pointing, but we like Tan Viet (3/100 John St) and Tuong Lai (3 Belvedere Arcade). Make sure to try a Vietnamese roll, a bowl of pho (beef noodle soup, or chicken if you must), some tiny little crisp spring rolls wrapped in mint and lettuce leaves and a sugarcane juice off the side of the street. From there it’s just a short waddle back to the station.

Tour Chippendale’s creative precincts


There are some 14 different galleries in the Chippendale area (that’s ‘Chippo’ to locals), and moving between them makes for a very pleasant stroll – why not see how many you can get to in one afternoon? Start at the Powerhouse Museum in Ultimo and then head to the contemporary Chinese art-focused White Rabbit Gallery, the DNA Projects, the UTS Gallery and MOP Projects. Finish by winding your way to the Pine Street Creative Art Centre and maybe having a bit of a sit down.

Visit the Golden Age Cinema

Surry Hills

Not only is the lovingly restored former Paramount screening room a gloriously intimate place to see a film – they mostly screen throwbacks and art-house fare – but it’s also a very chic bar.

Hear a tune in the Domain


The city parkland is lovely at any time, but during Sydney Festival it gets even better with free gigs like Chaka Khan (8pm, Sat Jan 11) and Symphony in the Domain (8pm, Sun Jan 26). 

Climb the Bridge

The Rocks

A visit to Sydney isn’t complete without wandering over its most recognisable landmark, right? There are various climbing options available at BridgeClimb – the company that started bringing people over the Harbour Bridge in 1998 – and all will see you tethered to a rope, wearing a blue jumpsuit and gaping at those crazy-good views 
of the city. Feeling thrifty? You get a pretty decent high-on-the-bridge experience just by heading up the Southeast Pylon to the museum 

Walk from Athol Bay to Chowder Bay


Explore the North Shore’s water’s edge and take in uninterrupted views of the Harbour that you don’t get to see from the south. Starting at Athol Bay (a perfect crescent of sand near the base of Taronga Zoo), the path snakes around Bradley’s Head and through scrubby bushland and grassy reserves to Taylor’s Bay. Eyes out for the more-onimous-sounding-than-it-actually-is Shark Island.

Snorkel at Shelly Beach


Grab a snorkel and goggles and discover the creatures that call this protected marine reserve just near Manly home. Friendly blue gropers, fluttering cuttlefish and even a mossy sunken motorcycle are just some of the treasures you’ll find below the surface at Shelly Beach.

Take the Botanic Gardens Aboriginal Heritage Walk


There are troves of native vegetation in the Royal Botanic Gardens, much of which was significant to Aboriginal culture. This self-guided walk shows off the Garden’s collection of native flora and explains their historical and cultural importance for the early inhabitants of the site, the Cadigal people.

Navigate Cockatoo Island

Sydney Harbour

This historic Sydney island – it’s been a naval storage facility, a factory and might well be haunted – is home to the Island Bar, where you can enjoy tropical cocktails and wood-fired pizza while perched on striped deck chairs overlooking Sydney Harbour. The island also plays host to regular big-ticket cultural events including the 19th Biennale of Sydney (Mar 21-Jun 9), and you can even camp or ‘glamp’ overnight in some very luxe tents with top-notch facilities.

Sneak backstage at the STC

Walsh Bay

Take a morning tour of the Sydney Theatre Company’s heritage-listed Wharf and get a behind-the-scenes glimpse of how they make magic in the costume and props departments and in the sets and art workshop. The tour is followed by lunch with a money-can’t-buy view of the Harbour at Bar at the End of the Wharf.

Spend a night at the museum


Put the art back in party: take in the latest shows at the Art Gallery of NSW and MCA after hours in nights packed with music, screenings and celebrity talks (and bars!). Art After Hours happens Wednesday nights 5-10pm at the Art Gallery of NSW while Lights on Later is on at the Museum of Contemporary Art, Thursday nights from 6-9pm. 

Sober up at Mr Crackles


Hit the sauce a little to hard? Need a late-night snack? A particularly porky one? There’s only one place for it and that’s the salty Oxford Street takeout joint, Mr Crackles. Get the Crackles Classic – a whole heap of crisp-skinned, slow-roasted pork belly served with Vietnamese salad in a roll ($10) and a cup of crackling ($5) on the side. Look through to the back kitchen and you can see the chefs hacking up the browned beasts: late-night-cravings heaven.

Hire a Tokyo Bike

Surry Hills

The very popular Tokyo Bikes are easy to ride and easy to carry (weighing between nine and 11 kilos). Since relocating to the beautiful Art Deco Paramount Building in Surry Hills, Tokyo Bike offers one-day bike hire for just $20. Pick up and return from their store during opening hours, but be warned: these bikes ain’t cheap – there’s a deposit of $600.

Give your credit card a work out on Paddington’s William street


Sydney’s best boutique shopping is in Paddington, and the city’s most stylish know to head to one particular laneway to browse luxurious collections from homegrown fashion designers. Lined with Victorian terrace houses, William Street is home to luxury basics brand Jac+ Jack, cult cashmere label Banjo & Matilda, Melbourne’s denim crusaders Nudie Jeans, and our favourite multi-label store, the Corner Shop. If your style icons include Kate Moss, Susie Bubble or Alexa Chung – you’ll be right at home here.

Splurge on vintage threads in Surry Hills


There are secondhand clothes shops dotted all over Sydney, from the more boho ’burbs of Newtown and Glebe to the yummy-mummy belts like Rozelle and Double Bay. But it’s in the 2010 postcode that you’ll find a close-knit community of vintage stores and retro fashion emporiums to take you from washed-out denim and threadbare band T-shirts to the funkiest ’50s, ’60s, ’70s and ’80s styles. Start at retro boutique Grandma Takes a Trip for party frocks and pearls and then drop into C’s Flashback for everything Lycra, sequined and metallic. Finish up in Miss Brown’s for cut-off denim shorts and modified beachwear from the ’50s and ’60s. 

Catch a short flick at Flickerfest


Sydney’s original outdoor cinema event, Flickerfest returns to the gorgeously old-world Bondi Pavilion (right on the beach!) for its 23rd year in 2014, with all the best international and local short films. Opening night includes a Blues Brothers-themed party and there are sessions for Documentaries, Animation, Celebrity Shorts and Kidsflicks. Be sure to be at Time Out’s special session of Short Laughs (Jan 12 & 18) for some seaside LOLs.

Spend Summer at the House


The Opera House programmers bring their A-game every sweaty season, and this year is probably the biggest line-up of shows and installations and generally awesome things to hit the sails yet: explore an inflatable city in the Opera House forecourt with Exxopolis (Jan 3-27); catch indie heroes Grizzly Bear (Sun Jan 5) and Yo La Tengo (Thu Mar 13) in the Concert Hall or the National in the forecourt (Feb 7-8); or get the young ones to kids show 13-Storey Treehouse (Dec 28-Jan 25). Plus there’s super-hot circus troupe La Soirée (Jan 7-Mar 16) and more.


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First published on 17 Dec 2012. Updated on 1 Jan 2014.

By Time Out Sydney editors   |  

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