A drone show over Sydney Harbour.
Photography: Supplied | Destination NSW | Daniel Tran | Written in the Stars drone show - Vivid Sydney

Things to do in Sydney in May

The temperatures outside may be dropping, but things are really hotting up in the city during the last month of autumn

Winnie Stubbs
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It's no secret that Sydney shines during the summer. But that's not to say that the colder months aren't also packed with good times in the Harbour City. This May, the city is coming alive with the giggly goodness that is Sydney Comedy Festival, where a bunch of very funny talents will be coming together to make our lives a little brighter. Adding to the illumination is Vivid 2024 – the immersive wonderland which will be lighting up the city from May 24. Until then, you can get your luminous fix at Luna Park’s Sonic Neon, or do as the Scandinavians do and heat things up at this stunning coastal sauna.

This month, we’ll also be hitting up this year’s incredible Biennale while we still can, stocking up on local goods at the best markets in the city, and warming up with a Sunday roast as winter sets in.

May the force be with us.

Stay in the loop: sign up for our free Time Out Sydney newsletter for more news, travel inspo and activity ideas, straight to your inbox.

If you want to bust outta town: Head on one of these dreamy short weekenders near Sydney, hit up one of NSW's best hot springs, and then stay closer to home with one of Sydney's easiest (and most beautiful) day walks. 

The best things in May

  • Drama
  • Sydney
  • 5 out of 5 stars
  • Recommended
Arthur Miller’s Pulitzer-winning 1949 play has lost none of its potency in the last 75 years. Indeed, in our current terrible moment of economic anxiety, the heaviest weight on Willy Loman’s back – the need to make his mortgage payments even as he’s rendered obsolete – will be familiar to many audience members, although perhaps one step removed. Director Neil Armfield and resident director Therésa Borg anchor this production in the period of the play’s genesis, but the themes remain timeless – beautifully and excruciatingly so. Anthony LaPaglia is our Willy Loman, making his Sydney stage debut at the Theatre Royal in the role that earned him standing ovations when this production debuted in Melbourne. Weighed down by years, responsibilities, and his own bulk, LaPagia’s Loman prowls the stage muttering, half lost in memories, pinning all his hopes on the illusory successes of his adult sons: wastrel womaniser Happy (Ben O’Toole) and former golden boy Biff (Josh Helman), high school football star turned frustrated drifter. Willy’s wife, the long-suffering Linda (Alison Whyte) dutifully dithers around her husband and boys, until she too fractures under the weight of Willy’s unrealised ambitions.  LaPaglia makes for an incredibly obstinate and frustratingly obtuse Willy, his crippling insecurities masked by a thick armour cast from bluster and bravado. Yes, it’s all about the American Dream and the failures thereof – but it’s worth noting that the American Dream has always been A
  • Circuses
  • Redfern
More than ten years since its premiere, this spectacularly saucy cabaret show – from the talented people who brought us the brilliantly outrageous Blanc de Blanc – is back on the Sydney stage. Popping up at The Grand Electric, Limbo The Return will feature a seductive mix of cabaret, circus and acrobatics, performed with a heart-pounding soundtrack and reality-altering lighting. The international cast features Bulgarian aerialist Maria Moncheva (Harry Potter – Germany), slack rope daredevil David Marco and fire-eating singer Clara Fable.The creators of the show originally put together an internationally renowned show Strut & Fret, which gained fans across the world (including Madonna, who went to see it twice during its London season). The follow up show – Limbo Unhinged – played at the Sydney Opera House back in 2018, and Sydney-based fans will finally be able to reconnect with the spellbinding cabaret-style performance. With the same creative team at the helm, audiences can expect a similar calibre at Limbo The Return: with wildly-impressive acrobatics, titillating circus performances and an ecstatic soundtrack. Composed by New York’s Jank maestro Sxip Shirey, the live music – described by Creative Director Scott Maidment as “a New Orleans brass bands meets the Beastie Boys on the way through Berlin, looking for a house party,” – is one of the main drawcards of this year’s show.  Set in an imaginary space between heaven and hell (hence the name), Limbo The Return has been e
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  • Musicals
  • Darling Harbour
  • 4 out of 5 stars
  • Recommended
This is it, we have found the yassification of Shakespeare. Fuelled by a playlist of certified pop hits, this jukebox romp billed as “the greatest love story ever remixed” poses a simple but provocative question: What if, instead of joining Romeo in eternal slumber, Juliet decided to live? A contagiously joyous musical spectacular, & Juliet has finally landed at Sydney’s Lyric Theatre after being met with critical acclaim on Broadway and the West End, not to mention the rapturously received Australian debut in Melbourne.  Filled with sing-a-long-able chart-topping bangers made famous by the likes of Britney Spears, The Backstreet Boys, Katy Perry and more from the songbook of Grammy-winning Swedish songwriter/producer Max Martin, the Aussie cast is overflowing with talent in this feel-good, flashy production. & Juliet is Shakespeare remixed for the girls, the gays and the theys... [but does it] really cut it as the feminist reclamation that we are promised? Will you be entertained? Absolutely. Does & Juliet set a new standard for jukebox musicals? Yes. Will you see one of the most diverse and charismatic casts of triple-threats ever assembled on an Australian stage? Heck yeah. Does the story deliver on the feminist retribution we are promised? Not quite. “What if Juliet didn’t kill herself?” Anne Hathaway (played by the enthralling Amy Lehpamer) posits to her husband, William Shakespeare (the ever-charming Rob Mills). “She’s only ever had one boyfriend, and frankly, the endi
  • Music
  • Jazz
  • The Rocks
To bring a little musical joy to the Harbour City through the cooler months, Sydney’s historic waterside precinct The Rocks is hosting free jazz performances every Thursday throughout winter – with live performances by musicians from around Australia. Jazz Sessions in The Rocks will run from 6pm until 9pm every Thursday between Thursday, May 9 and Thursday, August 29 – so there’s plenty of time to catch the star-lit shows.  Local distillery Hickson House Distilling Co will be slinging gin-based cocktails (including $12 Negronis), and there are a host of excellent restaurants in the area to keep you nourished pre and post show. The full season-long line-up is yet to be released, but in May, we can expect alfresco performances from Sydney-based jazz sweetheart Kate Wadey (Thursday, May 9), fantastical four-piece Cope Street Parade (Thursday, May 16), multi-disciplinary artist Alice Terry (Thursday, May 23) and the ever-soulful Latin/ jazz singer MIRA (Thursday, May 29). The events are free to attend and there’s no need to book. You can learn more over here. Stay in the loop: sign up for our free Time Out Sydney newsletter for more news, food & drink inspo and activity ideas, straight to your inbox.   RECOMMENDED:  Want more evening entertainment? These are the best bars and pubs in Sydney for live music. And these are the best musicals to catch this month. Need fun now? Here’s what’s on in Sydney this week.
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  • Shopping
  • Markets
  • Eveleigh
Carriageworks Farmers Market
Carriageworks Farmers Market
It’s imperative that you do not eat before you visit the Carriageworks Farmers Markets. You’ll want to save maximum belly space for your personal version of The Bachelorette where you decide who gets your dollars and what delicious produce gets to come home with you. Maybe you like something soupy and savoury first thing? In that case head to Bar Pho for a traditional Vietnamese start to the day. On the veggie train? Hit up Keppos St Kitchen for a falafel breakfast, or head to Food Farm for a classic bacon and egg roll.Once the hounds of your hunger have been quieted it’s time to prepare for your next meal, or seven. Stock up on artisan cheese from Leaning Oak, smoked salmon from Brilliant Foods and Sydney’s favourite sourdough from AP Bakery and brunch is sorted. You can spend a whole lot of money if you want to here, but equally you could just grab a kombucha on tap from Herbs of Life and find a chair for some of the best dog-watching in the city.   Hungry for more? Look at our list of the best markets in Sydney – produce or otherwise. 
  • Musicals
  • Elizabeth Bay
  • 4 out of 5 stars
  • Recommended
When an entire teen choir is suddenly killed in a tragic roller coaster accident, they awaken to find themselves in a strange carnie limbo. Greeted by an ominous robotic fortune teller, these misfits are invited to compete for the chance to return to the land of the living. This is the premise of Ride The Cyclone – the exciting, modern, TikTok-viral Canadian musical that is now playing its Aussie premiere season at Sydney’s intimate Hayes Theatre. Dark yet camp, nihilistic yet strangely life affirming, this show is full of surprises and just as brilliantly bonkers as it sounds.  Corralled and narrated by the legendary Pamela Rabe as the (studio-recorded) voice of The Amazing Karnak, a fresh young cast has been assembled to take on some of the most compelling characters in modern musical theatre, and there’s not a weak link among them (if only the same could be said for the fateful carnival ride on which their characters meet their untimely demise). Melding with the production’s other-worldly audio-visual elements, Rabe’s inimitable voice is the perfect pick for the mysterious fortune-telling automaton, lending a certain gravitas with a vaguely threatening, strangely alluring mythical quality – like a Matrix villain procreated with a wise wizard matriarch.  In Ride The Cyclone, modern, relevant and youthful references fit comfortably and casually within the musical theatre form, and this accomplishment is certainly key to the show’s popularity with Gen Z. The characters dreamt
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  • Shopping
  • Markets
  • Willoughby
Spend a leisurely Sunday morning in France without the jet lag at these fabulous French markets in Sydney’s north. Le Marché is the only fortnightly French market in the whole of Australia, popping up every second and fourth Sunday of each month at Laurelbank Cottage in Willoughby. Here, you can say bonjour to more than 45 talented Frenchies selling everything from raclette and rillettes to choux buns and Champagne.   Start your morning in Le Marché’s culinary corner, which channels the vibes of a mini French supermarket. Fill your reusable baskets with farm-fresh eggs, truffles, saucisson, duck confit and of course, all the French cheeses your heart desires. Thirsty? Take a detour to sample fine French wines and locally brewed gin, or skip straight to the Champagne bar for a bubbly start to your day.  Experience the lively spirit of a French village market by chatting with Le Marché’s passionate line-up of artisans selling striped Breton t-shirts, colourful berets, linen tablecloths, straw baskets and more. Take a leisurely browse through the stalls, and when it's time to refuel, hit up the hot food stalls serving everything from buttery escargots and boeuf bourguignon to raclette and truffle-infused rotisserie chicken. Seal the deal on your market rendezvous with a flaky croissant, creamy eclair or delicate choux bun. Bring a taste of the markets home too by buying a freshly baked baguette or colourful box of bite-sized macarons.  RECOMMENDED: Hungry for more? Look at our
  • Health and beauty
  • Manly
In excellent news for sauna lovers, what began as a dreamy pop-up has now become a (relatively) permanent feature at Manly’s Quarantine Beach. The 10-person Finnish sauna from Cedar the Salt will be stationed on the shores of Sydney Harbour throughout the winter – offering a very Scandinavian experience from arguably the most stunning sauna location in the city. Sydney's first pop-up seaside Finnish sauna launched as a thirteen day pop-up, but due to huge demand (around 150 sauna-goers per day), it will be staying put until spring. A 45-minute ocean-side sauna experience will set you back $35, and you’ll have easy access to the ocean to cool off between steams. If you’re keen to take over the entire sauna for a celebratory sweat, private sauna sessions are also available, and there's a soundbath experience available for those who went to level up their relaxation. If you want to make the seaside sauna a regular component of your wellness routine, you can nab a pack of three, five or ten sauna sessions.  The sauna is open from sunrise (between 6.30am and 7.15) until sunset (around 4.30pm), seven days a week, with the current closing date currently estimated at "springtime". Keen? You can learn more and book your session over here. Stay in the loop: sign up for our free Time Out Sydney newsletter for more news, travel inspo and activity ideas, straight to your inbox.   RECOMMENDED:  We tried this beautiful affordable bathhouse. These are Sydney’s best spas.These are the best da
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  • Shopping
  • Markets
  • Paddington
Paddington Markets
Paddington Markets
Every Saturday, more than 100 stalls line the grounds of Paddington Uniting Church and the neighbouring public school selling Australian-made fashion, handmade crockery and metal costume jewellery. The market has been operating on the same day since 1973, and the all-weather event is a profitable fundraiser for the church. Many of the stallholders return week on week, like the elderly Japanese couple selling Bonsai trees and the Spanish shoemakers selling espadrilles. It’s predominantly an art, clothing and design market – and alongside the kitsch bric-à-brac and Australiana-print tea towels you’ll find straw hats from local milliners and soft Tunisian-made ‘Turkish’ towels from young Eastern Suburb entrepreneurs. Antique, vinyl and vintage stalls are few and far between, but leather satchels, beach photography prints and patterned baby rompers are two a penny. On a hot day locals gather at the shaded tables and stools by the snack stalls. Turkish women hand roll yufka dough at the gözleme tent and vegetables are blitzed in a blender at the fresh juice stand. Chin’s Laksa stall, proudly MSG and gluten free, is a popular choice – as are the vegan cookies and sourdough scones on offer at the bakery stalls. It has a bohemian flair compared to its Oxford Street location and customers joyfully take up fortune readings, as well as reiki and Japanese massage. It’s an oddball mix, but one that works strangely well in an area known for its designer boutiques and gentrified pubs. Ou
  • Shopping
  • Markets
  • Kirribilli
Kirribilli Art, Design & Fashion Markets
Kirribilli Art, Design & Fashion Markets
Fans of expertly curated market events such as the Finders Keepers will be happy to know there is a bi-monthly market offering a comparable experience a stone’s throw from Luna Park. The second Sunday of every month sees the art, design and fashion iteration of Kirribilli’s historic (est 1976) markets, centred on the weather-proof location of the Burton Street Tunnel right under Milsons Point Train station.  You’ll find quirky millinery by Nitascraft, hilarious knitted parrots, octopuses and Barbie outfits by Irene, and cool laser-etched wooden phone cases by Bare-wood. An antiques corner features groovy typewriters from the 1960s and several stalls offer funny and handmade greeting cards. Vintage spoons are refashioned as bracelets, and if you’ve ever hankered after a large photographic portrait of a wombat, you can get it here – the place is a goldmine for non-tacky Sydney souvenirs. On the last Saturday of the month is the general and fashion market, where punters have been known to snap up luxurious, one-of-a-kind finds from labels like Gucci, Zimmermann and Acne, thanks to the well-heeled crowds selling their wares. Arrival by train is recommended as parking is expensive and hard to come by.  There is an excellent food court area where you can get a roast pork roll, quesadillas, churros, gözleme, paella, blynis, dim sum, banh mi or gelato and sit down undercover to eat them while watching a talented teenage girl reinventing ‘Sweet Child ‘o Mine’. Afterwards, head over t
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