The best things to do in Sydney and beyond based on your favourite season

From cosy winter escapes to golden autumn road trips, Sydney and New South Wales offer year-round adventures
Sydney
Photograph: Shutterstock
Time Out Singapore in partnership with EU Holidays
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Living in Singapore means you pretty much get summer all year round – and while we love our fun in the sun, sometimes you just want to swap it out for cosy winter hideaways, golden autumn leaves, or a bloom-core spring adventure with your besties. That’s where Sydney comes in.

Just under eight hours by flight from Singapore, Sydney and its dreamy New South Wales surroundings offer the ultimate four-season escape. From skiing down the slopes of Snowy Mountains and hiking up the magnificent Blue Mountains to soaking up the breezy Bondi mornings, there’s always something worth hopping on a plane for. And the best bit? Every season feels like a whole new trip.

Spring: September to November

When the flowers begin to blossom, Sydney feels like it’s waking up with a smile. The days are bright, the skies are clear, and the weather is just right – not too hot, not too cold – making it the perfect time to explore the city in bloom.

Start with a walk through the Royal Botanic Garden, where cherry blossoms and jacaranda trees put on a pastel-hued show. Or hop on a ferry to Taronga Zoo – it’s not just the animals that shine, but the stunning harbour views and blooming landscapes all around. And if you’re visiting between May and November, keep an eye on the horizon – you might just see whales from coastal trails or on board a scenic whale watching cruise.

For a dose of art in the open air, don’t miss Sculpture by the Sea from October 17 to November 3, 2025, when the Bondi to Tamarama Coastal Walk is transformed by more than 100 dramatic installations perched along the clifftops – it’s the largest free outdoor sculpture exhibition in the world.

Over at Barangaroo Reserve, native flora bursts into colour and waterside paths lead to art installations, pop-up events, and buzzy new dining spots. It’s also one of Sydney’s best picnic locations – BYO cheese and bubbles, or grab gourmet takeaway nearby. Join an Aboriginal cultural tour, stroll the Wulugul Walk, or cool off at Marinawi Cove while you're there. 

Want to make a weekend of it? Head to the Hunter Valley for a sunrise hot-air balloon ride over vineyards, or time your trip with Tulip Time in the Southern Highlands from September 12 to October 6, 2025 – a colourful flower festival in Bowral that brings spring to life with over 75,000 tulips.

Time Out tip: With EU Holidays’ range of Sydney travel packages, you can tailor your trip to your spring-loving heart’s content.

Summer: December to February

If you’re the type to plan your holidays around how much vitamin D you can soak up, Sydney shines under the summer sun, with its famed beaches and coastline, alfresco dining culture, and splash-worthy getaways all playing lead roles. 

Kick off your morning at Bondi Beach – one of the best spots in Sydney to catch your first wave or at least wipe out in style. Once you’ve towelled off, swap the board for walking shoes and hit the Bondi to Coogee coastal walk. This scenic trail hugs the cliffs, with dramatic ocean views, salty breezes and locals sipping flat whites at cafés along the way. Don’t forget to snap a pic at the iconic Bondi Icebergs Pool before following the winding path around the headland.

When the sun’s at its highest, head north to Port Stephens, about a two-and-a-half-hour drive away. Perfect for aquatic adventures, this coastal gem is where you can hop on a dolphin-watching cruise, try your luck at sandboarding on the massive dunes, or just laze on soft sands with the sounds of the sea for company. 

And if the kids are tagging along, you're in for a wild ride. Visit Irukandji Shark & Ray Encounters for hands-on marine fun, then swing by Oakvale Wildlife Park for kangaroo meet-and-greets, baby farm animal bottle-feedings, cow milkings, and the occasional crocodile cameo. Want to really up the adventure? Hop on a camel at Oakfield Ranch and trot along the dunes of Port Stephens.

Time Out tip: Make the most of your sun-soaked holiday with EU Holidays’ eight-day Sydney, Port Stephens and Wildlife Family Fun itinerary.

Autumn: March to May

This is the perfect time to escape the city buzz and head west to the majestic Blue Mountains. Here, the air is cooler, the waterfalls are mistier, and the eucalyptus-cloaked cliffs seem to glow in the autumn light. Meander through charming towns like Katoomba and Leura, where you can warm up with hot scones in heritage tearooms, or take the Scenic Railway through the rainforest – it’s the steepest of its kind in the world, but you’ll be rewarded with incredible views. 

For a proper hit of autumn foliage, head to the Southern Highlands or Orange – two of NSW’s most charming regions come to life this time of year. Expect tree-lined streets awash in amber and gold, cosy cafés tucked into historic towns, and cool, crisp air perfect for fireside wines. Whether you're browsing weekend markets in Bowral, Southern Highlands or munching your way through a food festival in Orange, it’s the kind of countryside escape that feels like a warm hug in your best knitwear.

Time Out tip: With EU Holidays’ Best of Sydney and Beyond: Blue Mountains itinerary, you’ll tick off all these autumn gems without having to lift a planning finger.

Winter: June to August

While Sydney stays frost-free, the Snowy Mountains deliver the real white winter deal – and they’re only a short trip away. Whether you're carving up the slopes in Thredbo or Perisher, or cosying up in lakeside Jindabyne, this is your chance to trade city life for snow-dusted peaks, après-ski sessions, and all the hot chocolate your hands can hold. 

If you’re not ready to hang up the beanie just yet, extend your stay in the Blue Mountains. Winter turns the region into a magical escape – think misty trails, crackling fireplaces, and charming lodges that feel like something out of a fairytale. Don’t miss a stargazing tour while you’re there – the skies are clearest in winter, making it the perfect time to spot constellations above the dramatic clifftops.

Back in the city, winter is prime time for culture. Roam through the Art Gallery of New South Wales, catch a play at the Sydney Opera House, or join the locals on the harbourside for Vivid Sydney, Australia's largest festival that turns the city into a glowing wonderland of art, music and creativity, with the next one planned for May 22 to June 13, 2026.

Time Out tip: EU Holidays’ winter itinerary bundles up all these highlights – city icons, mountain moments, and a little luxury along the way – into a seasonally snug getaway.

Whether you’re escaping the heat, chasing the sun, or timing your trip with nature’s best moments, you’ll find the perfect experience in every season. Discover more seasonal Sydney travel packages with EU Holidays here.

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