MJ - The MusicalCredit: Myles Frost as Michael Jackson in the original Broadway production of MJ_photo by Matthew Murphy
MJ - The Musical
When the winter sun signs off, Sydney’s technicolour skyline roars to life, setting the stage for a spectacular calendar of world-class events that intrigue, inspire and thrill. And, as the entertainment hub of the Southern Hemisphere, the city’s hotlist of happenings is ever-growing, with the cooler months ahead bringing an unmissable lineup of festivals, international sports tournaments, and blockbuster shows. With comfortable temperatures and bright, clear nights, there’s never been a better time to experience the energy and excitement of Sydney. Here, your winter-night hitlist…
Level up your winter festivities
Crackling with energy 24/7, Sydney doesn’t snooze through winter, it celebrates. So, consider the season’s festivals your personal invitation to recharge your inspiration in a city-wide playground of imagination, family fun and unexpected wonders.
Become part of something larger than life as Vivid Sydney lights up the city from 23 May to 14 June, with more than 300 events forging new pathways to awe through Light, Music, Food and Ideas. Familiar streets feel beautifully otherworldly as Circular Quay, The Rocks, Barangaroo, Darling Harbour, The Goods Line and beyond reveal their glow-ups for this year’s festival theme, Dream. From the 8km Light Walk to the Vivid Fire Kitchen and the family-friendly concerts of Tumbalong Nights, you’ll find countless new ways to imagine, feast and play over 23 technicolour nights.
Anchored by the iconic State Theatre and stretching out into neighbourhood cinemas from Newtown to Randwick, the 72nd Sydney Film Festival opens its curtains from 4 June with more than 250 screenings to level-up your movie nights. Showcasing emerging creatives and established filmmakers from across the globe, this year’s program features a stellar lineup of indie award winners, lauded documentaries and dramas you won’t usually find in the multiplex cinemas. Grab some popcorn and step behind the scenes for conversations with cinema’s game-changers, including director Liam Young and composer Forest Swords.
The feelgood festivities flow on throughout July and August, with the Bondi Festival and Darling Harbour’s Winterfest bringing the winter cheer with everything from pop-up ice-skating to live comedy.
Add your voice to the stadium’s roar
Follow the roar of the crowds into stadiums abuzz with electric energy as winter nights set the scene for some of sport’s fiercest showdowns. The action’s headlined by two unmissable rugby union blockbusters, as the mighty British & Irish Lions return to Australia for the first time in 12 years – and they’re coming straight for NSW’s biggest stages. On 5 July, more than 45,000 fans will pack out the stands of Allianz Stadium to watch the NSW Waratahs take on the touring powerhouse. Then, on 2 August, all eyes turn to Accor Stadium for what could be the deciding Test match in the Lions’ nine-game tour. The footy action continues with rugby league’s ultimate grudge match, the State of Origin. On 9 July, more than 80,000 fans will watch the NSW Blues defend home turf against the Queensland Maroons in the epic series decider at Sydney Olympic Park. The state-against-state energy carries on at ICC Sydney, where the PBR Origin sees the Professional Bull Riders Monster Energy Tour deliver a heart-pounding ride in the ultimate battle of precision, power and fearless skill.
Vivid Sydney 2025 Credit: Destination NSW
Error is Inspired by the idea that Dreams, like the unpredictable glitches in technology, embody both the chaos and creativity that propel us into new realms of possibility. Artist - Vendel en de Wolf, Light Art Collection
Vivid Sydney 2025 Credit: Destination NSW
Error is Inspired by the idea that Dreams, like the unpredictable glitches in technology, embody both the chaos and creativity that propel us into new realms of possibility. Artist - Vendel en de Wolf, Light Art Collection
Spend your nights singing along
Warm up your vocal cords: this winter, the Harbour City’s blockbuster musicals will have you humming and buzzing long after their curtain call. Leading the charge is The Book of Mormon at the Capitol Theatre from 15 July – an outrageously witty global phenomenon from the creators of South Park, sure to leave you singing, gasping and belly-laughing. At the Sydney Lyric Theatre, MJ: The Musical brings the moves, music and magnetism of Michael Jackson to the stage, diving deep into his artistry with jaw-dropping choreography and iconic songs. Add the Céline Dion-infused spectacle Titanique, the return of Cats for its 40th Australian season, and a boldly reimagined Carmen at the Sydney Opera House, and you’ve got a cold-season lineup that’s anything but chilled. Are smaller-scale gigs more your speed? Keep your eye on the calendars of Mary’s Underground and the The Vanguard, Enmore, and Metro theatres for live concerts to keep you moving every winter night.
Go exploring on clear winter’s nights
Across Sydney, moonlit meanders lead to surprising, invigorating happenings. On Friday nights from 4-11pm, an evening stroll through neon-lit Dixon Street becomes a unique shopping adventure through the weekly Chinatown Night Market. Soak up the lively atmosphere and live music as you treasure-hunt through an ever-changing lineup of 50 stalls offering everything from hand-crafted noodles and dumplings to one-of-a-kind handicrafts from up-and-coming artists. In eclectic Darlinghurst, the Darlo Village Night Markets run from 4- 9pm, every third Saturday of the month, warming your winter nights with delicious food, live music, and a welcoming community vibe on the grounds of the St John’s Anglican Church. Prefer to leave the bright lights behind for a night-time stroll in nature? Grab your torch and head to Western Sydney Parklands for a winter walk on the wild side on 20 June, joining a ranger-guided nocturnal wildlife walk in search of brushtail possums, microbats, tawny frogmouths, grey-headed flying foxes, and a menagerie of other native animals that come out to play after sundown (be sure to book asap as places are filling fast).
Embrace all things theatrical
Take your seat for an evening of enthralling live performance as the city’s stages pulse with stories, movement and laughter. At the Sydney Opera House, Bangarra Dance Theatre returns with Ilume (4 -14 June): a bold new work that explores our light within. Then, hear the venue’s Drama Theatre bellow with laughter as the Olivier and Tony Award-winning comedy, The Play That Goes Wrong, unleashes its side-splitting chaos from 19 June.
Be moved by powerful storytelling as living legends such as Rebecca Gibney and Cameron Daddo step centre-stage at the Sydney Theatre Company for the powerful Circle Mirror Transformation (from 12 July) and as Judy Davis and Elizabeth Alexander star in Helen Garner’s classic, The Spare Room, at the Belvoir St Theatre. The iconic Australian stories continue in Western Sydney, with Looking For Alibrandi, 1984, and Trophy Boys bringing the premium drama to Parramatta’s Riverside theatres.
The Vanguard, Newtown Credit: Destination NSW
Patrons enjoying drinks and live music at The Vanguard, Newtown in Sydney's inner west.
The Vanguard, Newtown Credit: Destination NSW
Patrons enjoying drinks and live music at The Vanguard, Newtown in Sydney's inner west.
Riverside Theatre, Parramatta Credit: Destination NSW
Audience watching a Aboriginal performers on stage at the Riverside Theatre in Parramatta
Riverside Theatre, Parramatta Credit: Destination NSW
Audience watching a Aboriginal performers on stage at the Riverside Theatre in Parramatta
More Inspirational Stories
The Day Spa by Chuan, at The Langham, SydneyCredit: The Langham
Set underground at The Langham, Sydney, The Day Spa by Chuan boasts a 20m heated pool.
The cooler days have arrived, but that doesn’t mean you need to hang up your swimming cap – for many locals, a winter dip is the perfect way to refresh, reset and feel new. Whether you’re plunging into a brisk ocean pool to enliven every sense, chasing your personal best in a heated Olympic pool, or floating on your back in an exclusive indoor waterhole, here’s everything you need to dive into winter in Sydney – where the water is warming all year round.
Immerse in a luxury stay
As the big chill takes hold, Sydney’s luxury hotels become the ultimate relaxation stations, where heated pools become balmy oases to soak away the everyday. And whether you’re up for endorphin-drenched laps or a laidback float under the stars, you’re spoilt for choice on the Harbour’s banks and beyond.
In Barangaroo at Crown Sydney, the city’s first infinity pool offers 28°C waters, jaw-dropping views over the harbour and private poolside cabanas that make every dip inspiring and indulgent. Just a short stroll away, W Sydney’s 30m rooftop pool is perched high above Darling Harbour on Level 29, offering daybed lounging by day and luminous skyline views by night, while a sleek indoor pool on Level 22 keeps the warmth flowing round the clock. Nearby, the Shangri-La Sydney’s charming 13m heated pool is ideal after a session at their award-winning spa or a fine-dining feast overlooking Circular Quay. In Millers Point, The Langham Sydney’s serene 20m pool is crowned by a star-dappled ceiling, while Radisson Blu Plaza Hotel Sydney cocoons its inviting 15m heated pool inside beautiful, reimagined heritage walls.
Prefer your own private Airbnb haven? Cosy up in a luxurious two bedroom apartment on the water’s edge for access to indoor and outdoor pools, as well as steam rooms and spas; or set your sights on the Spa Serenity cottage in Seaforth, where a private pool and hot spa are all yours, 24/7.
Swim laps around winter
Sydney’s landmark Olympic pools have long been at the heart of the community – these are the places that have made history, sparked dreams, and kept the city moving for generations. Perfect your tumble-turn in the hallowed pools of the Sydney Olympic Park Aquatic Centre, home to some of the world’s greatest sporting moments since the Sydney 2000 Olympic and Paralympic Games. Carve through four indoor heated pools, unwind in the spa and sauna, or let the kids blow off steam in the Splasher’s Water Playground, where slides, water cannons and a rapid river ride bring the splashy fun.
InUltimo, you can swim in the wake of one of Australia’s most iconic Olympians at the Ian Thorpe Aquatic Centre, with three indoor heated pools, a state-of-the-art fitness centre, and sleek, modern design just minutes from Darling Harbour.
Closer to Central Station in Surry Hills, locals flock year-round to the historic Prince Alfred Park Pool, a 50m outdoor heated offering surrounded by lush lawns, tennis courts, fitness stations and dog-friendly spaces. And keep your goggles handy: North Sydney Olympic Pool, long considered the world’s most spectacular swimming pool thanks to its dazzling harbourfront setting – beneath the Sydney Harbour Bridge and next to Luna Park – is set to reopen this winter after a major revitalisation project.
Wherever you mount the starting blocks, Sydney’s Olympic pools will leave you energised long after you’ve towelled off.
Crown Sydney, Barangaroo Credit: Destination NSW
Couple enjoying the luxurious pool at Crown Towers hotel, Crown Sydney, Barangaroo.
Crown Sydney, Barangaroo Credit: Destination NSW
Couple enjoying the luxurious pool at Crown Towers hotel, Crown Sydney, Barangaroo.
Darling Harbour, Sydney Credit: Destination NSW
City views featuring King Street Wharf, Cockle Bay, Darling Harbour and the Sydney CBD.
Darling Harbour, Sydney Credit: Destination NSW
City views featuring King Street Wharf, Cockle Bay, Darling Harbour and the Sydney CBD.
Take an invigorating cold plunge
Promising a brisk hit of Vitamin Sea to shake up your circulation for head-to-toe revitalisation, Sydney’s ocean pools sing their siren’s song all winter long, tempting the brave to meet the season head-on. Between Cronulla and Palm Beach, more than 35 ocean pools transform the coast into a playground of salt-sprayed invigoration – even when the water’s temperature is a chilly 16-18°C.
Right alongside Bondi Beach’s golden sands, Bondi Baths set the benchmark. Home of winter swimming since 1929, their 50m ocean-fed pool and separate kids’ pool invite you to test your mettle with every frosty lap – all against a backdrop of iconic beach views – then thaw out with a warm drink in Bondi Icebergs afterwards. Or hotfoot it with locals along the Bondi to Coogee Coastal Walk, pausing for a float and soak in the ocean-fed lap pool tucked into the southern headland at Bronte, before continuing on to Coogee. Here, Wylie’s Baths have enticed wintertime swimmers since 1907, with sweeping views across Wedding Cake Island and a historic timber promenade adding to the ambience. A further 7km south, Malabar Ocean Pool offers protected waters, fewer crowds, and the chance to spot fish darting below.
Sydney Harbour’s cool waters set the stage for refreshing dips, too. The Murray Rose Pool in Double Bay is a netted haven with calm waters and a welcoming community vibe. And at Mosman’s Cremorne Point, the glamour of the city skyline and Harbour Bridge views frame every stroke at the 33m Maccallum Pool.
Rug up for an adrenaline rush
Feel the thrill of a cool-season adrenaline hit with a host of quintessentially Sydney activities, both in and on the water. Zip up your winter wetsuit for a snorkel in the Cabbage Tree Bay Aquatic Reserve in Manly, where fewer swimmers mean better wildlife encounters, especially in the rocky shallows. Home to more than 150 species of marine life, here you might spot cuttlefish, gropers, Port Jackson sharks, rays, turtles, dolphins and even distant humpback whales. Or, head to Gordons Bay, a hidden cove between Clovelly and Coogee, for a signposted underwater nature trail leading through shimmering schools of fish and swaying seaweed gardens.
For a heart-pumping rush in perfect barrels, don your steamer for a thrilling winter surf session at URBNSURF Sydney. Here you can expect hundreds of perfectly curved waves every hour as well as formal lessons tailored to your experience, a Surf Academy, and a hot lagoon-side leisure pool to warm up between rides – all just 20 minutes from the city centre.
Prefer a more peaceful paddle? Brave the chill for a sunrise kayaking tour on Sydney Harbour with Sydney By Kayak. Paddling out as the city skyline glows to life is an unforgettable way to start your winter morning – complete with coffee on the water and unbeatable Harbour Bridge views.
Wherever you take the plunge this winter, you’ll discover the city’s waters – cold, hot, and everything energising in between – are inspiring, thrilling and truly extraordinary. But that’s Sydney for you.
Sydney Kayak Experience, Sydney Credit: Destination NSW
Friends enjoy the unique experience of a Sunrise Kayak Tour with Sydney Kayak Experience, Sydney.
Sydney Kayak Experience, Sydney Credit: Destination NSW
Friends enjoy the unique experience of a Sunrise Kayak Tour with Sydney Kayak Experience, Sydney.
URBNSURF Sydney Credit: Applejack_Sandy's_URBNSURF Sydney
URBNSURF Sydney
URBNSURF Sydney Credit: Applejack_Sandy's_URBNSURF Sydney
URBNSURF Sydney