Beloved King St boozer the Newtown Social Club was re-invented as Holey Moley in July 2017, combining playful cocktails and a modern pub grub menu (think bao burgers and sweet potato fries) with the zaniest putt putt course you could imagine – nine holes of cartoonish mini-golf through a graffitied van, a billiards table, a glistening golden bathroom, and even a Game of Thrones style throne made of putters. It’s super popular so best to make a booking so you and your date don’t miss out.
387 King St, Newtown NSW 2042, 1300 727 833
Introducing the best vantage point of Sydney Harbour you’ve never heard of. Hidden away on Cremorne Point on the Lower North Shore, this seawater swimming hole and its timber deck is literally perched on the edge of the harbour, ringed by a pristine park that couldn’t be more perfect for a picnic and a sun-bathe with bae.
Booze and dates are a winning combination, so start your exploration of Sydney’s booming micro-brew scene with a few frothies at Newtown institution Young Henry’s before rolling down the hill to St Peters’ Willie the Boatman and Sydenham’s Batch Brewing Co. All offer tasting platters and finger food in trendy industrial-chic spaces.
Young Henry’s 76 Wilford St, Newtown NSW 2042, +61 2 9519 0048
If you’re looking for something harder, head to the Archie Rose Distillery in Rosebery – the first distillery to open in Sydney since 1853 (that’s a long time between drinks). The copper and exposed brick revamp of a converted warehouse won the distillery the title of Best International Bar at the Restaurant and Bar Design Awards in London in 2015, and the gin won best in class in the contemporary gin category at the American Distilling Institute awards in 2017… and if that doesn’t impress your date, nothing will.
85 Dunning Ave, Rosebery NSW 2018, + 61 2 8458 2300
Offering to spend the night is a bit too presumptuous for a first date, but a spot of glamorous camping – or glamping – is a brilliant romantic retreat for couples. Cockatoo Island– a fascinating colonial-era convict site and the largest island in Sydney Harbour – and Taronga Zoo – which offers luxury ‘Roar and Snore’ packages in tents overlooking the water and the city skyline – are the city’s top two picks.
Sydney’s blessed with plenty of great kayaking spots but Rose Bay – home to some of the city’s most coveted real estate – is the premier launching pad for a paddle around the harbour, especially if you’re feeling energetic enough to reach the verdant Shark Island (which, contrary to its name, isn’t brimming with Great Whites). Rose Bay Aquatic Hire, opposite the Rose Bay RSL Club, provides kayak, boat, and stand-up paddle board hire.
Unless your partner’s claustrophobic, an escape room is a brilliant idea for a date, working together as a team to solve your way out of trouble – and the brainiest escape in Sydney is Next Level’s literary-themed Ex Libris, one of the few independent escape rooms in the city. The puzzles have been set by a pair of former economists for the Reserve Bank of Australia, so you know they take some serious grey matter to solve.
Level 2/37 Bligh St, Sydney NSW 2000, +61 457 000 036
If you’re trying to appear a little more cultural in the eyes of your date, hit up the Art Gallery of NSW on Wednesday nights for Art After Hours – an ever-changing calendar of events including expert talks, guided tours, dance performances and live music. And the best bit? Admission doesn’t cost a cent, avoiding any awkward conversations about going Dutch on the bill.
Art Gallery Rd, Sydney NSW 2000, +61 2 9225 1700