Cockatoo Island

If there’s one thing Sydney does spectacularly well, it’s slow summer evenings – the kinds that see the sky turn sherbet-pink and the whole city look a little softer around the edges. This summer, Cockatoo Island/ Wareamah is handing us a very solid excuse to make the most of it: Sunset Sessions is back, taking over the lawn of historic Biloela House with a weekly dose of live music in the open air. Running on Saturday evenings from January 10 2025 to April 4 2026, the island’s curated open-air gig series is one of those annual events that reliably sells out – and for good reason. The formula is foolproof: pack a picnic rug, stretch out on the grass and let a line-up of emerging local artists soundtrack the slow fade into night as the sun sets behind the city. RELATED READ: These are the best sunset spots in Sydney This year brings a particularly juicy mix of genres and rising talent to Sydney Harbour’s largest island. Expect lush vocals from Charlie Collins, dreamy pop by Mia Lovelock, and globe-spanning grooves courtesy of Immy Owusu and Dom Diaz. You’ll also catch Merpire, Joel Leggett, William Alexander, Dave Graney, Joe Mungovan, Clay Western, Cooee and Luke Saunders – with more artists still to be announced. If you’re not the type to pack your own snacks, Biloela House will have refreshments ready to go – or you can pre-order a hamper of treats when you book your ticket. And if you’ve ever entertained the fantasy of running away to an island for the night, Cockatoo...

The Sydney Harbour Concours d’Elegance is back for its eighth year, bringing rare, classic and ultra-luxury vehicles to the Southern Hemisphere’s most glamorous automotive showcase. To celebrate its return, organisers are adding a brand-new (and completely free) opening event to the program. On February 26, head to Bennelong Lawn for a sneak peek at 30 of the world’s finest cars, set against the sparkling backdrop of Sydney Harbour. Drop by between 10am and 12pm to admire the display, then catch the cars as they depart in convoy over the Harbour Bridge at 1pm en route to Cockatoo Island, where the main event runs from February 27 to March 1. Want more than just a preview? Time Out readers can score 20 per cent off tickets to the three-day event on Cockatoo Island by using the code 6XP6K6X2 at checkout. Across the weekend, expect everything from vintage classics to cutting-edge supercars and hypercars, plus the latest in energy-efficient vehicles. There’s also a curated wine and cheese experience each day, and on the final day an international panel of experts will crown the prestigious Best in Show. To secure your discounted tickets, head here.