
The Ultimate Winter Road Trip for Big Experiences
When the temperature drops, it’s time to turn up the adventure. Winter along the Grand Pacific Drive isn’t just about scenic pit stops and coastal views – it’s about chasing those once-in-a-lifetime moments.
Picture this: skydiving over a sun-kissed coastline, spotting humpbacks breach just offshore, wandering through world-class art museums, or stargazing under a velvet sky on a white-sand beach.
From the wild to the whimsical, the South Coast and Southern Highlands are packed with experiences that make you feel alive, even when your breath fogs up the air.
Ready to chase some grand winter magic? Let’s hit the road.

Wollongong: Thrills, Tranquillity & Wildlife Encounters
Wollongong knows how to do grand – and winter is one of the best-kept secrets for making the most of it. First up: skydiving. Yes, skydiving in winter. With clearer skies and calmer winds, cold-season jumps with Skydive Sydney–Wollongong offers unbeatable views of the coast, the mountains, and your courage levels skyrocketing. You’ll free-fall over one of Australia’s most iconic beaches, and the bragging rights are as epic as the experience.
Balance the adrenaline rush with a soul-soothing visit to Nan Tien Temple, the largest Buddhist temple in the Southern Hemisphere. Wander through peaceful gardens, admire the intricate architecture, or even join a mindfulness session – it’s the perfect way to reset and recharge on your journey.
And for something wildly heartwarming? Head just north to Symbio Wildlife Park, where you can hand-feed kangaroos, snap a selfie with a koala, or meet exotic animals from around the globe. It’s family-friendly, feel-good, and pure winter magic.

Shellharbour: Whale Tails, Jet Thrills & Mini Golf Madness
Shellharbour may be small in size, but it delivers big on adventure – especially in winter. For starters, this is prime time for whale watching with Shellharbour Wild. Set sail on a coastal cruise and watch as majestic humpbacks breach, slap their tails, and glide gracefully along their migration path. It’s the kind of experience that makes you gasp out loud – and maybe shed a little awe-inspired tear.
If you prefer your thrills in the sky rather than at sea, buckle into the cockpit with Jetflight Shellharbour. This is no ordinary scenic flight – you’ll soar above the South Coast in a real ex-military jet before diving into an adrenaline-fuelled aerobatic routine of loops, rolls, and wingovers. It’s wild, unforgettable, and definitely one for the bucket list. While you are at Shellharbour Airport, make sure you visit the HARS Aviation Museum, here you can climb into the cockpit of an F-111 jet fighter while it’s still on the ground and take a walk on the wing of the record-breaking jumbo jet – Qantas Boeing 747.
Then, bring it back to ground level with a dose of competitive family fun at Mini Golf at The Links Shell Cove. This isn’t your average mini golf – it’s a big on fun scaled-down replica of a real golf course, complete with bunkers, greens, and a challenge level to suit everyone from pint-sized beginners to expert golfers. It’s the perfect way to wind down after a big day – or to fire up a little friendly competition before your next adventure!

Kiama: Tree-Top Views, Coastal Cruising & Creative Moments
Kiama is the kind of place that invites you to slow down, look up, and lean into the joy of discovery – whether you’re gliding through a rainforest canopy, pedalling beside ocean views, or getting inspired by local makers.
Start your day above it all at Illawarra Fly Treetop Adventures, where panoramic rainforest views stretch all the way to the coast. Wander the elevated steel walkway that winds through the canopy or climb the spiral stairs of Knights Tower for a breathtaking lookout. Feeling brave? Clip in for the Zipline Tour – Australia’s highest – and soar between tree platforms with nothing but the wind (and a lot of laughter) in your ears. It’s a forest experience like no other, and it’s even better in the cool, clear winter air.
Next, swap the treetops for the coastline with a spin on two wheels from Kiama Cycles and Sports. With gentle power-assisted rides, you’ll cruise along seaside paths and winding country roads, taking in all the charm of the region without breaking a sweat. Whether you’re a weekend wanderer or a cycling pro, there’s a route to match your pace – and the views are worth every turn of the pedals.
Round out your visit with a dose of handmade magic at Soul Clay Studios in Gerringong. This welcoming creative hub is home to a community of ceramic artists crafting beautiful, functional pieces in the heart of town. Watch the artists in action, browse the shelves for a one-of-a-kind souvenir, or take a behind-the-scenes peek into the studio where each piece is thoughtfully made. Or why not enjoy a one-off air dry or wheel throwing class? It’s art you can touch – and take home.

Shoalhaven: Whales, Stars & Deep Connection to Country
Down in the Shoalhaven, we invite you to slow down, look closer, and feel something deeper – whether it’s the stillness of the bush, the vastness of the night sky, or the heartbeat of ancient culture.
Begin your journey at Woebegone Freedive, where adventure and nature collide in an unforgettable way. Dive into the crystal-clear waters of Jervis Bay, where you’ll explore the stunning seal colonies, migrating humpback whales, hidden sea caves, and pristine white sandy beaches. Whether you’re embarking on a beach or boat snorkelling expedition or seeking to refine your skills with a Freedive training course, Woebegone Freedive offers the ultimate underwater experiences. Don’t miss their biggest winter treat – the Swim with Whales Expedition, running from June to October. This extraordinary opportunity lets you swim alongside the majestic humpback whales in their natural habitat, a truly once-in-a-lifetime adventure.
As night falls, swap gallery lights for starlight with Jervis Bay Stargazing. Led by a passionate astrophysicist, this unforgettable beachside experience lets you explore the cosmos far from city glare. With the waves as your soundtrack, you’ll learn how to read the sky, track satellites, and even spot shooting stars – all while being wrapped in the wonder of where the sea meets the stars.
For a truly grounding and powerful experience, join Gadhungal Marring’s Raymond Timbery in Huskisson for a cultural immersion that will stay with you long after your trip. From smoking ceremonies and dance to bush food knowledge, mangrove walks, and yarns around the fire, these on-country teachings are a profound way to engage with the living culture of the First Nations people – and see this land through a different lens.

Southern Highlands: Scenic Drives, Cosy Fires & Wine for Days
Winter in the Southern Highlands is crisp, calm, and quietly spectacular – a place where misty mornings give way to golden afternoons, and every turn down a country lane feels like stepping into a storybook.
In the Southern Highlands, grand experiences await you around every turn. Meander through rolling green hills, picture-perfect pastures and timeless stone walls on one of the region’s many scenic Tourist Drives. One of our favourite routes? Start with a coffee in Bowral, then wind your way east to Robertson along the tourism road. With breathtaking views and countryside charm that feels straight out of a dream, you’ll be tempted to leave the city behind for good. Cap off your drive with a hearty meal at the historic Robertson Public House or the ever-charming Moonacres.
If your idea of bliss is fireside comfort, you’ve come to the right place. The Highlands is home to more Fireside Escapes than anywhere else in NSW – from boutique stays with crackling hearths to cosy galleries and retail spaces offering glowing refuge from the winter chill. Book a country cottage or stylish hotel, pour a glass of Pinot, and let the fire do the rest. For a more adventurous twist, dine under the stars at a fire feast experience at Osborn House or Eschalot, or join the magic of Midwinter Festival this July.
Looking for a fireside chat with locals over a soul-warming drink? Try the historic charm of Surveyor General Inn in Berrima, or sip and stay at much-loved venues like Taylor’s Inn, Berida Hotel, Peppers Craigieburn, Centennial Vineyards, Robertson Hotel, and Burrawang Hotel.
And what’s winter without red wine? Discover the Southern Highlands Wine Trail – a full day (or weekend!) journey through award-winning vineyards, boutique cellar doors, and spirited distilleries. From crisp whites to bold reds and local liqueurs, it’s an experience that’ll warm your heart and tempt your palate at every stop.
So, there you have it – a road trip bursting with grand experiences from coast to country. Whether you’re free-falling over Wollongong’s coastline, whale watching in Shellharbour, exploring rainforests in Kiama, connecting to culture in Shoalhaven, or soaking up the crisp, creative charm of the Southern Highlands, winter is anything but sleepy on the Grand Pacific Drive.
So, pack the beanie, charge the camera, and hit the road – your grandest winter yet is waiting.
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