Sydney’s summer is undoubtedly one of the best in the world, whether you’re soaking up the sun on Bondi Beach, enjoying outdoor seating at a sleek wine bar or trekking along one of the city’s famous coastal walks. That being said, winter in Sydney has a special place in my heart.
The cooler weather brings in fewer tourists, but the city stays alive with events, from the legendary Vivid Sydney multi-arts festival to the arrival of migrating whales breaching off the coast. Sydney Comedy Festival eases us into the temperature change with laughs across the city, while the world’s biggest fun run, City2Surf, celebrates dedicated runners racing through Sydney’s most iconic streets.
Now is not the time to mourn the summer, but instead to celebrate what Sydney has to offer as a winter destination. Here’s what we’re most excited about for the upcoming months.
Whale watching
There’s something very special about whale season in Sydney. As tourism to the city slows down, humpback whales begin their migration along the coast, from around mid-May to November.
Peak periods of whale activity are usually in late June to July for the northern migration, but my favourite time to spot whales is around September to October, as young calves will often be in tow for the southern return.
Whether you’re looking for whales on one of Sydney’s famous coastal walks or have opted to book a specialty whale watching cruise, winter provides plenty of opportunity to spot these beautiful creatures from both land and sea.
Sydney Comedy Festival
Sydney Comedy Festival returns for five weeks of non-stop laughter, taking over the city with a host of international and emerging comedy legends.
In 2025, more than 160,000 people attended shows across the Festival, with events like Great Laugh In The Park and Gala on the Green attracting roughly 12,500 people with their community comedy takeovers. 2026 sees the program evolve further, offering over 380 shows across April and May from upwards of 1000 talented comedians, actors and artists.
13 festival hubs will host 50 stages, and whether you’re catching shows in the North at The Concourse Chatswood, The Joan in Penrith, Bondi Pavilion in the East or Marrickville’s Factory Theatre, the vibes will be high, and the laughs will be loud. It’s exactly the kind of event Sydney needs as we approach colder weather.
Vivid Sydney
The iconic multi-arts festival Vivid Sydney will return to the city from May 22 to June 13. This year’s edition is shaping up to be extra exciting, thanks to the return of its beloved drone show, and exclusive foodie events from superstar chefs, including Yotam Ottolenghi, Mindy Woods and Danielle Alvarez.
They’re also upgrading their free light shows, with Australia’s most ambitious free outdoor laser spectacular set to illuminate the harbour and over 38 searchlights ready to light up landmark buildings and locales. You can check out the upcoming Vivid Sydney program here.
The return of the roast
Sydney has no shortage of standout pubs, many of which serve up indulgent Sunday roasts piled high with rich gravy, perfectly cooked meats and all the trimmings you could ask for.
My top picks include the Sunday roasts at the Village Inn in Paddington ($29), the Lord Dudley in Woollahra ($28), Forrester’s iconic Big Yorkie (from $38), and the Lord Nelson’s generous three-cuts feast for two ($70).
These pubs are known for their cosy, old-English vibe, making them the perfect setting to embrace the winter and tuck into a hearty but warming feast.
City2Surf and Sydney Marathon
As someone who decided to don their running shoes and take on the dreaded Heartbreak Hill in last year’s City2Surf, I’m one of the biggest cheerleaders of this annual event. City2Surf is the world’s biggest fun run, drawing in over 80,000 to 90,000 participants yearly, who take on the 14km run from Hyde Park to Bondi Beach (aka, the city to the surf).
Even if you’re not lacing up, heading down to the course to cheer from the sidelines is one of April’s highlights, as the city comes together to celebrate each runner.
City2Surf returns on August 9, followed by the Sydney Marathon just three weeks later on August 30. Another city-wide spectacle, this year’s marathon marks its second as an Abbott World Marathon Major, and it’s set to be the biggest yet, with a record 40,000 finishers expected after unprecedented demand.
Enjoy the thriving morning economy
Everyone knows that Sydney is a great place to watch a sunrise, just ask the hundreds of people who swarm Bondi Beach at ungodly hours, flat white in hand and activewear on.
Although daylight savings means that it gets darker much earlier in Sydney, it also means that it gets lighter earlier, so if you’re a morning person, it’s your time to shine. Join one of the many Sydney run clubs that hit the tarmac early on, or head to the beach before work for an invigorating ocean dip that will be sure to wake you up.
Sydney Film Festival
The 73rd Sydney Film Festival (SFF) will take place from June 3 to 14, offering up a 200-plus strong program of incredible cinema. One of the world’s long-running and most prestigious film festivals, SFF showcases the best in contemporary cinema at venues across Sydney, while also offering audiences the chance to experience premieres, red carpet events and exciting special programs.
The SFF has already offered a glimpse of its upcoming program, with internationally acclaimed titles like The Blood Countess, Dead Man’s Wire, Erupcja and Broken English all set to make their Australian premieres.
The Lion King
In very exciting news for Sydney’s theatre fanatics, blockbuster musical The Lion King will return to the Harbour City in April. The original Australian production of The Lion King premiered at the Capitol Theatre in Sydney in October 2003, returning for a second run ten years later in December 2013, and now back again to the iconic venue 13 years later. The musical, which has won six Tony Awards, including Best Musical, will officially open on April 18 for a strictly limited (but highly anticipated) season. The cast will star Aphiwe Nyezi as Simba, Emily Nkomo as Nala, Nick Afoa as Mufasa and Buyi Zama as Rafiki.
Click here to find out more about the upcoming production.
Where: Capitol Theatre, 13 Campbell St, Haymarket NSW 2000.
When: April 18-August 9, 2026.
Price: From $165.
