It finally feels as though that autumn chill has hit – and in Sydney that means a few things: holing up in cosy bars, an excuse to avoid the “cold” weather by testing buzzy new diners and, of course, the beginning of Vivid. May might be when we usually go into hibernation – but after two years of staying at home it’s time to unleash ourselves on the city again and enjoy it to its utmost. Below are my top picks for what to do this month. And you can follow my May here.

Prize-winning paintings
Filmmaker and actor Taika Waititi, Midnight Oil frontman Peter Garrett and writer and broadcaster Benjamin Law’s butt are just some of the subjects of this year’s Archibald Prize finalists. The winner – as well as the winners of the Wynne and Sulman prizes – will be announced this Friday May 13. The blockbuster exhibition – one of Australia’s most visited – opens on Saturday May 14. Works I’m most excited to see in the flesh include Natasha Walsh’s witty tribute to Brett Whiteley’s 1976 Archibald winner Self-portrait in the Studio, titled Dear Brett (The Blue Room), and Vincent Namatjira’s vividly articulated Self-portrait With Dingo. The exhibition runs until August 28.

Phoenix rising
Behind a shapely facade on O’Connor Street in Chippendale lies breathtakingly beautiful performance and gallery space Phoenix. Not only is it an incredible piece of architecture, backed by arts philanthropist Judith Neilson, but it’s also home to an ongoing series of live performances – which are intimate (only 120 people fit in the performance space) and entirely free. Upcoming shows worth registering for include fascinating electronic producer Jonti and Melbourne producer and vocalist Ijale, whose work is influenced by his Nigerian heritage.

Out of this world
Enmore Road isn’t short of a good bar (see: Jacoby’s and Fortunate Son). But the street’s latest addition, Bar Planet, from the Cantina OK team, is worth a visit – especially if you dig a Martini. The classic cocktail is the lynchpin of the menu here – and while there’s a house Martini, you can also get it made as dirty, wet or otherwise as you like. A particular highlight of a Bar Planet visit are the porrons – large decanters found in Spain – from which the Martinis are theatrically poured from on high.

Parlar games
Aiming to transport you a little closer to Earth is new Potts Point diner Parlar. From the team behind neighbouring bistro Franca, it’s putting a fine-dining spin on Catalan cuisine in a glowing tapestry-lined dining room. Highlights of its share menu include a churro topped with anchovy and crème fraîche; all the fixings of a classic gilda (anchovy, olive, guindilla) on toast, instead of on a traditional toothpick; and a supersized vol-au-vent with escalivada (roasted vegetables) and a good amount of manchego. Wash it all down with an Alcazar – the diner’s spin on a Manhattan – it’s made with Johnnie Walker Black, sweet vermouth, Strega (an Italian herbal liquor) and a cinnamon tincture and topped with a maraschino cherry.

Light it up
Vivid. It’s back. For the first time in two years it looks as though Vivid is making it to the opening date with no lockdowns or restrictions to get in its way. This year, under new festival director Gill Minervini, the festival is a paean to Sydney – to its people, its resilience and its love of a bloody good time. The line-up this year is huge, spanning lights, music, ideas and, this year, even food. While its light walk will always draw crowds, there’s plenty else to love. A dinner created by Dan Hong and Mike Eggert, with music and Ken Done projections. Leigh Sales interviewing screenwriter and director Aaron Sorkin of The West Wing and The Social Network fame. Japanese “neo-kawaii” rock group Chai. Weekly supper clubs at Mary’s Underground. And so, so much more. See you out there.