Laneway bars serving pasta, salty ocean pools, a skydive before breakfast and a 1920s picture palace: here is how to spend four days in Wollongong and the arty, cliffside villages to its north.

Having run off the cliff edge at Hill 60 strapped to a hang glider, I can tell you the sudden rush of the experience is unforgettable. From up there, you get a true seabird’s view of the Illawarra: forest-cloaked cliffs plunging into a sapphire-blue sea and whitecapped waves rising and crashing against the rock platforms.

Whether soaring above it or driving the coast road from Sydney’s south to the Gong, I’ve spent more than a decade exploring the beaches, bars and dining scene in Wollongong. My verdict? A long weekend in Wollongong now serves up as much genuine culture and action as coastline.  Framed by towering sandstone escarpment on one side and breaking swell on the other, this four-day itinerary wanders from laneway trattorias and contemporary galleries to windswept lookouts and the creative enclaves of Thirroul and Austinmer.

Day 1: Galleries, laneways and the Blue Mile

Download the Spotify playlist of Tell Them Their Dreaming by First Nations (Jawoyn) artist Troy-Anthony Baylis ahead of the 90-minute drive down from Sydney. The playlist features queer icons such as Kylie Minogue and Mariah Carey as well as Wollongong’s own legendary rock band, Tumbleweed. It’s the perfect soundtrack to ease into your weekend at Wollongong Art Gallery, one of the largest regional galleries in the country, housed inside the stately former council chambers. Entry is free and director Daniel Mudie Cunningham’s program seamlessly weaves live performance and music among visual exhibitions. Don’t be alarmed if a painting seems to be singing back at you. While in the Wollongong Arts Precinct, stroll across the civic plaza to the Illawarra Museum – set inside the 1882 former post office – or see what’s on stage at the neighbouring Illawarra Performing Arts Centre, managed by Merrigong Theatre Company.

Wander east toward the harbour where the blue water is smudged along the margins of the Blue Mile, a scenic foreshore path linking Wollongong Harbour to North Beach. Pack your bathers and goggles. Swimmers have been churning out laps in the historic Continental Pool since 1926 – its name a nod to the once-scandalous European custom of mixed-gender ‘continental bathing’.

Settle in for sundowners at Five Barrel Brewing, an independent, family-run brewery that was converted from a commercial warehouse to a craft brewery while maintaining its artfully scuffed industrial aesthetic. The hand-pumped cask ales cater to beer nerds who appreciate a slow, classic pour. The taproom has 21 craft beers on tap accompanied by burgers and loaded sides from the Five Barrel Food Truck.  You could also fill a weekend in the Gong celebrating the booming craft beer and spirits scene at Seeker Brewing, Principle Brewing, First Light Brewing and Resin Brewing or sipping botanical gins at South Coast Distillery.

When darkness falls, slip into Globe Lane, one of the atmospheric alleyways keeping the CBD humming after hours and powering the city’s nightlife. While you could spend a whole week exploring the best restaurants in Wollongong, make Restaurant Santino a must-do on day one. Brought to you by the team behind Kneading Ruby, the moody, Art Deco-accented trattoria features low lighting, handmade pasta crafted daily and a wine list that justifies that second glass of nebbiolo. It will take you about two minutes to stroll back to the retro-cool Surfside 22, your stylish beachfront base for the next few days.

Day 2: Skydives, serenity and harbourside seafood

Kick off the day at dawn with Skydive Wollongong, the region’s premier beach skydive experience. Leaping from 15,000 feet, you’ll experience up to 60 seconds of heart-stopping freefall before the entire Illawarra escarpment and coastline are revealed beneath you as you float back down to Earth with a soft touchdown at Stuart Park right by North Beach.

If you’d rather carve up the waves than plunge from the sky, book a surf lesson with Illawarra Surf Academy. If wet weather rolls in, trade the sand for high-speed indoor electric karting at C1 Speed. Otherwise, steady your pulse over brunch at Diggies, a landmark café at North Beach that has championed local Illawarra produce since 2004.

Trade adrenaline for tranquillity at Nan Tien Temple in Berkeley, the largest Buddhist temple complex in the Southern Hemisphere. Stroll through peaceful lotus gardens beneath the eight-story pagoda, then enjoy traditional vegetarian afternoon tea at the Tea House. (Note: The temple is closed on Mondays).

Wrap up the evening right on the water’s edge at Harbourfront Seafood Restaurant, anchored at the edge of Belmore Basin for more than three decades. The market menu changes daily with the morning’s haul and watching the local fishing fleet bobbing right outside your window in Wollongong Harbour makes the ultimate case for ordering the catch of the day.

Day 3: Sea cliffs, ocean pools and village life

Drive north for morning coffee and fresh sourdough at Bread, Espresso &, a hole-in-the-wall Thirroul institution that has drawn a steady queue of surfers, locals and sleepy weekenders since 2015. Grab a warm pastry for now and stash another for the road.

Continue up to Bald Hill Lookout, where aviation pioneer Lawrence Hargrave famously launched into the sky anchored to four box kites in 1894. Look up and you’re likely to see a flock of hang gliders, their neon wings suspended like giant sea birds over the ocean. If visiting between May and November, you can book a scenic flight with Touchdown Helicopters and scan the horizon for migrating humpback whales from above. Those who prefer to stay grounded can simply stroll the 665-metre curve of Sea Cliff Bridge, which snakes dramatically out over the crashing surf between Coalcliff and Clifton. Or swap the heights for a horseback trek through bushland with Otford Valley Farm Horse Riding or Darkes Forest Riding Ranch.

Clinging to the cliffside above the breaking swell, The Imperial at Clifton is a historic miners’ pub that stood shuttered for nearly two decades before reopening with its magnificent heritage framework restored. Secure a table on the front terrace for sprawling sea cliff vistas or retreat indoors beside one of five original open fireplaces if the southerly buster arrives.

Cool off with a dip in Austinmer’s twin ocean pools, carved directly into the rock platform, then check into Headlands Austinmer Beach, where the beachfront suites sit a mere Frisbee’s throw from the sand.

Spend the afternoon fossicking for treasures at Thirroul’s independent galleries and vintage shops before pulling up a chair at Pickled Poet, an intimate wine bar and deli. Share a curated grazing board paired with small-batch Australian wines and then catch a gig at Anita’s Theatre. Originally opened as the King’s Theatre in 1925 and later transformed into a roller-skating rink, this lovingly restored venue stands as the Illawarra’s premier performing arts hall, hosting live music and comedy under its ornate ceiling.

Day 4: Escarpment peaks and one final dip

Set the alarm so you can ascend Mount Keira (Djeera to the Dharawal and Wodi Wodi Traditional Custodians) to reach Mount Keira Summit Park, offering panoramic views across Wollongong’s grid out toward Port Kembla. Active travellers can hike the surrounding Mount Keira Ring track starting from Byarong Park, where emerald-green subtropical rainforest envelops the escarpment trails. As the Southern Hemisphere’s first designated UCI Bike City, Wollongong is also best explored on two wheels; mountain bikers can hit the dedicated singletrack at Mt Kembla Mountain Bike Trails, while recreational cyclists can cruise the city’s extensive coastal cycleways which stretch from North Wollongong Beach down to the Wollongong Golf Club.

Wollongong Botanic Garden, at the mountain’s base, sprawls over 27 hectares and includes the Towri Bush Tucker Garden. Book an Aboriginal-guided walk with Gumaraa to experience First Nations culture during an immersive walk on country – crushing lemon myrtle between your fingertips, discovering native plants used for ancestral bush medicine and tasting wild food while listening to Dreaming stories.

Conclude your long weekend with one final, farewell swim at Bulli Rock Pool, a classic 50-metre rock pool carved into the headland since the 1930s. As ocean waves crash against the outer walls and the afternoon light honeys the escarpment, the city hustle of Sydney will feel a world away.

Break up the journey back to Sydney with a visit to Symbio Wildlife Park in Helensburgh to hand-feed kangaroos and meet koalas. As you merge back onto the highway toward Sydney, salt on your skin, you won’t come away feeling like you’ve ticked off a touristy checklist. Like me, you will leave with a greater appreciation for the Gong, a sophisticated city that has completely redefined itself.