Rub the Lucky Pig's NoseOutside Sydney Hospital on Macquarie Street, find Il Porcellino, the bronze boar with a snout polished gold by a million superstitious hands. Rub it, drop a coin, and walk off luckier and slightly weirder.CultureEasy15 min
Stand Under 180 Singing Empty CagesDuck into Angel Place laneway, between George and Pitt Streets, and look up at the suspended birdcages of Forgotten Songs. They are empty, but they sing the calls of 50 birds Sydney built over. Eerie and beautiful.Hidden GemEasy20 min
Find the Crumpled Paper BagTrack down the Dr Chau Chak Wing Building on Ultimo Road, Frank Gehry's only Aussie work. Locals call it the squashed brown paper bag. Decide for yourself whether 320,000 wonky bricks count as genius.Photo HuntEasy20 min
Find Wendy Whiteley's Secret Garden in Lavender BayBehind Luna Park in Lavender Bay, find Wendy Whiteley's Secret Garden, built by a grieving widow on abandoned railway land. There are no signs in. That is the point. Wander the zigzag paths until you are pleasantly lost.Local DetailEasy45 min
Hunt Down Newtown's Famous WallAt 305 King Street, Newtown, find the heritage-listed I Have A Dream mural, painted illegally over two nights in 1991 and now Australia's most photographed wall. Add your own snap to the millions.CultureEasy20 min
Eat a Democracy SausageHit a Bunnings Warehouse on a weekend and order the sacred sausage sizzle: a greasy snag on white bread, onions, and a violent squirt of sauce, all for a few dollars. Folding the bread correctly is a national skill.Food & DrinkEasy15 min
Photograph a Forest Growing From a ShipWalk to the Shipwreck Lookout at the end of Burroway Road, Wentworth Point, and spot the SS Ayrfield: a century-old rusting hull with a whole mangrove forest sprouting from its deck. Sunset turns it into a postcard.Photo HuntMedium1 hr
Survive the Stairs of DoomClimb the McElhone Stairs from Brougham Street, Woolloomooloo, up to Potts Point: 113 sandstone steps locals nicknamed the Stairs of Doom. Residents sip tea on balconies watching you wheeze. Give them a show.ActiveMedium20 min
Find the Stream That Built SydneyInside the GPO building on Martin Place, hunt the lower level for the little Tank Stream display: a glimpse of the hidden creek that is the only reason the colony settled here. A whole city's origin story, tucked in a nook.WeirdEasy20 min
Walk Through a Fridge Into a BarIn Manly, find Cove Deli, then locate the antique 1920s refrigerator at the back. Open it, descend the spiral stairs, and emerge in The Cumberland, an underground drinking den hiding behind the cheese.SocialBold1 hr
Run the Bondi to Coogee at sunriseLace up and jog the 6km clifftop coastal walk from Bondi before the day-trippers arrive, dodging local runners and stopping only to gawk at the ocean. Coogee Beach is your finish line, and the swim afterwards is non-negotiable.ActiveMedium1 hr 15 min
Loop the Bay Run with the inner-west crowdTackle the flat 7km circuit around Iron Cove that local joggers, skaters and pram-pushers swear by. Start at King George Park and go early, because by weekend mid-morning the whole inner west is out here.ActiveMedium1 hr
Swim laps in a 1907 tidal pool at Wylie's BathsDip into the heritage-listed ocean pool at Coogee that's been flushed by the tide twice a day since 1907, where Olympic swimmer Mina Wylie once trained. Float on your back, watch the boardwalk above, and pretend you're an Edwardian athlete.ActiveEasy45 min
Go feral in the WILD PLAY treehouseTurn the kids loose in the free Ian Potter Children's WILD PLAY Garden inside Centennial Park, where dry creek beds, a bamboo forest and the park's first treehouse beat any indoor play centre. Bring a towel, because the artesian water-play area always wins.FamilyEasy1 hr
Engineer a flood at Darling QuarterHand the kids the sluice gates, pumps and water wheels of the free Water Works playground behind the IMAX, and let them redirect rivers like tiny civil engineers. There's also an 8-metre slide and a flying fox, so nobody leaves dry or calm.FamilyEasy1 hr