After being lulled to sleep by breaking waves in the charismatic New South Wales bolt-hole of Kiama, I swapped the caress of the coast for the heights of hinterland, with a swing through the Southern Highlands of New South Wales. I was heading for Bowral, before completing my southern self-drive, by looping back to Sydney. A coast and highlands self-drive combo is the winning formula for a magical roadie from Sydney. Pulling out of Kiama, I ventured west on Tourist Drive 9 to Robertson, a stirringly picturesque driving route that winds through lush and rolling hills and dales, criss-crossed with quaint leafy lanes, on its steady climb into the Highlands.

Rolling through such a bucolic escape-hatch from the rat race, I was struck by the hundreds of dry stone walls that lace the landscape, interwoven into the dreamy tapestry of pastoral greens. Had a leprechaun spirited me away to Ireland? It turns out that many of the walls were constructed in the 19th century and have stood the test of time. Many of them are attributed to Thomas Newing who soldiered away, building wall after wall for over 60 years! If you’ve done some pre-trip planning, you’ll soon discover there are a plethora of delightful detours and stopovers along the way. Jamberoo is a charming village en-route, with an Insta-worthy Tudor-style historic inn lording over the main street. It’s a perennial favourite amongst classic car clubs undertaking a group roadie. From there, I headed up Jamberoo Mountain Road, and took the short diversion to Minnamurra Rainforest, a rare remnant of temperate rainforest thronging with ancient fig trees, rock orchids and elkhorns.

A sense of serenity washed over me as I strolled up the path to clap eyes on the sublime Minnamurra Falls, gracefully tumbling over the canyon’s cliff edge. Back in the car, I purred through the forest-draped mountain road to reach Robertson, famous as the town where the BABE film was made. They’re also very proud of their potatoes, Robo Spuds. Like all towns and villages across the Southern Highlands, I soon discovered they are particularly parochial about their prowess in pies. With more pie outlets per square km than anywhere else in Australia, the region has crafted a dedicated Pie Trail, with scores of outlets touting their hero product. June is prime “Pie Time” when an annual festival is staged on the back of the latest pie judging results. Robertson Pie Shop is a proven performer, if you’re feeling peckish. From Robertson, I took Tourist Drive 15, to layover at Fitzroy Falls, en-route to Moss Vale.

The Highlands brim with water-curtain spectacles, but Fitzroy Falls is the cascading king, with a spectacularly-sized waterfall and wonderful walking tracks, abuzz with wildflowers, wildlife and stirring views across sandstone escarpments. After recent rain, it’s euphoria-inducing. Moss Vale is a gem of a town, cultivating a fiendish following for its magnificent homeware specialty stores. Top stops include Bowerbird on Argyle, a luxurious emporium of fine textiles, artwork and quirky gifts, while Suzie Anderson’s Home is an equally elegant hive of homeware temptation and inspiration. Peckish? Hot-foot it to Bernie’s Diner, a Moss Vale main street institution for nearly a century, and proud winner of the region’s Best Pie last year. It’s a very short drive from Moss Vale to Bowral, the biggest town in the Southern Highlands, abuzz with attractions.

Cricket fans rejoice – Bowral is the hometown of one of the sport’s most famous sons, Sir Donald Bradman. I felt duly obliged to survey his home ground, picturebook-pretty Bowral Oval, which rubs shoulders with the Bradman Centre. This magnificent shrine to the Aussie legend, showcases over 35,000 artefacts, including bats, uniforms, trophies and film footage, stretched over five galleries. Immortalised in a life-size bronze statue next to the oval, the “Boy from Bowral” is not the town’s only famous resident. The creator of Mary Poppins, P L Travers, is also cast in bronze at Glebe Park, the statue pays tribute to the fact that she lived in Bowral from 1907 to 1917.

Bowral has carved out a solid reputation as a discerning destination for shoppers, whether it’s for fashion and designer accessories, collectibles, artworks or vintage wares. Driving down the town’s golden mile, the inimitably-named Bong Bong Street, the rain started tumbling in heavy, fat bullets. Eager to venture indoors, I headed for Dirty Janes. This remarkable emporium is spread across three repurposed warehouses, groaning with over 75 dealers specialising in quality vintage, antiques and retro goods, from all over the world. It’s a head swirl of retail discovery. And while you’re there, stake out The Potting Shed, which serves a smashing High Tea in its verdant courtyard. Another headline retail haunt in Bowral is the Royal Doulton Outlet shop, which also stocks prized pieces of Waterford, Wedgewood, Royal Albert and Littala at discount prices.

With the rain still bucketing down, I finished off my Southern Highlands foray, by spending a night at the Gibraltar Hotel Bowral, a leafy and luxurious country retreat, overlooking Gibraltar Country Club golf course and backed by the Gibbergunyah Reserve. Inspired by vistas of Mount Gibraltar, this contemporary designer hotel boats 76 luxurious rooms, where the furnishings are plush and the creature comforts are laid-on thick. I had the pleasure of dining at San Fior, where the culinary influence is ultra-global and artfully executed. I plumped for the Tandoori Lamb Rump, slow cooked in the restaurant’s tandoour and succulently marinated in rich tandoori spices. It’s served with bombay aloo, cucumber, yoghurt and chili.

San Fior is adjoined by the playful Harvey’s Bar, a superb space with an outdoor terrace overlooking the greens. They’re very proud of their splendid mixology menu and you must try the signature cocktail, a Southern Highlands Cooler. Ingeniously served in a bath tub-glass (which are frequently stolen), this blockbuster potion comprises vodka, butterscotch schnapps, malibu, midori, cranberry and orange. What a concoction! And what a salute to this salubrious pocket of New South Wales, pitch-perfect for a flavourful weekend roadie from Sydney.