The drive southwest from Sydney to Picton is only 85km, but arriving here is like stepping back in time. This historic town was one of the state’s first European settlements, with many of the 19th century buildings (not to mention railway tunnels) from this era impeccably preserved throughout leafy streets.

Among them is the George IV Inn, one of the oldest hotels in the country and a place for thirsty travellers to find respite since beer was first poured in 1835. Today, it’s home to a restaurant, bar and hotel rooms, with the outdoor area perfect for lunch in the sun.

A 10min walk north, the Picton Botanic Gardens is a glorious union of native and exotic flora, the grassy expanse along Stonequarry Creek webbed with walking and biking trails.

Follow Barkers Lodge Road northwest out of town to reach Mowbray Park Farmstay, a family owned working farm where you can partake in everything from pony rides and feeding animals to milking cows and collecting eggs.

On your way out of Picton veer north to Warragamba Dam, a gargantuan heritage-listed structure that creates the primary reservoir for Sydney's water supply.

It’s a 40min drive south to Thirlmere on the edge of Nattai National Park – on your way, visit Cedar Creek Orchard to continue your life-on-the-land lesson. This 45-hectare estate is planted with stonefruit, apples and persimmon. Pick your own, or head to the shed to purchase fruit, juice and cider to take away.

Within minutes of starting your engine you’ll be in Thirlmere, its heyday back in the 1860s when the Great Southern Railway line was constructed through its countryside. Re-live this history at the town’s NSW Rail Museum; the collection of more than 100 train-related artefacts is the largest of its kind in the country.

It’s time to stretch your legs at Thirlmere Lakes National Park, known for its expansive waterways enveloped by native forest. Bring your hiking boots and binoculars to spot everything from white-bellied sea eagles to white-faced herons. More trekking awaits on your way out of town at the Mermaid Pools, a large waterhole on the Bargo River. This is the start of Tahmoor Gorge, with a circuit trail revealing waterfalls and all manner of native wildlife – camera essential.

Your final destination for the day is Berrima, a 45min drive south in the Southern Highlands. This is Australia’s best-preserved Georgian town, with its long history chronicled at the Berrima District Museum.

Step outside for living history, the town’s streets a patchwork of heritage sandstone buildings home to antiques stores and cafes, and the Surveyor General Inn. It's the country’s oldest continuously licensed pub, frequented by Cobb & Co coach passengers back in the 1800s, and by thirsty road-trippers today.

Just around the corner is PepperGreen Estate, offering flights of the cool climate wines made here, paired with bites like seared scallops on pearl-barley risotto. The Southern Highlands is the closest wine region to Sydney, so it’s only fitting you continue your grape education at Bendooley Estate; begin with a wine tasting and grazing plate at the cellar door, then lose hours strolling the manicured grounds or in the atmospheric bookstore, replete with rare tomes housed under cathedral ceilings.

Time to leave town? Before exploring Bowral drop in on Eden Brewery, which produces tasty ales, ciders and stouts using sustainable practices.

It’s just a 10min drive to neighbouring Bowral, the largest town in the Southern Highlands and a place that unites cosy cafes and country markets with fine-dining restaurants and award-winning wineries. Case in point is Centennial Vineyards, where neat rows of grapes are turned into everything from sparkling wine to rosé to reds. Visit the cellar door for tastings, tour the grounds or linger in the restaurant, with unbroken estate views.

Tractorless Vineyard not only picks fruit by hand, but also grows grapes using biodynamic principles – the ‘lawnmowers’ here are sheep, wandering between vines and trees in the olive grove. Once you’ve sampled wines, discover the estate’s Bowral Brewing Company beers.

There are two other notable Bowral drawcards. The first: incredible seasonal flora, casting the colours of the rainbow over Corbett Gardens, where the annual Tulip Time Festival sees 75,000 blooms on display. The other: this town was the boyhood home of legendary cricket player, the late Sir Donald Bradman. If you don’t know anything about the game, the Bradman Museum and International Cricket Hall of Fame is enlightening. If you’re a fan of the sport, this is cricket heaven.

You can drive directly to the Kangaroo Valley – a small town shrouded in rainforest – in 40min. But the ideal route has a few tasty, and scenic, detours. Birch Restaurant, in Moss Vale, has an innovative menu which features local and native produce, like kangaroo loin with saltbush and pepperberry. Just down the road in Exeter you’ll find St Maur Wines, a family-owned estate dedicated to sustainable farming. Sip pinot noir or chardonnay at the cellar door in the company of the estate’s wine dog, Sienna.

Head south through Morton National Park, the star of which is Fitzroy Falls. Amble along boardwalks to glimpse the cascade tumble 81m over cliffs into the deep valley below.

You’ll feel like you’ve been transported to medieval times when you reach Hampden Bridge – replete with gothic sandstone towers, it's the country’s last surviving wooden suspension bridge. Instead of entering a castle, you cross to arrive at Valley Outdoors. The team here organise canoe hire and guided trips around a number of the region's waterways, including Bendeela Recreation Area and the surreal sunken forests of Tallowa Dam. Keep watch for kangaroos on the shore and eagles overhead.

Reward your hard work with a culinary experience via Wild Food Adventures, which takes you out for a day of delicious adventure – think canapés, champagne, winery visits and upscale meals paired with canoeing and stargazing.

Driving east from the Kangaroo Valley to Berry, your backdrop is the Cambewarra Range and Budderoo National Park. You’ll leave the rainforest behind as you near the coast, where Berry’s heritage buildings are encircled by oak, elm and beech.

Today is one of indulgence, beginning with cinnamon doughnuts from the Berry Donut Van – 55 years of experience goes into every bite. A short stroll away is The Treat Factory, where you can pick up chocolate coffee beans, apple chutney and ‘jackeroo’ dukkah.

Travel northeast to Gerroa where Surf Camp Australia is based. Here, pull on a wetsuit and get some tips on tackling the South Coast’s waves. Once you’ve dried off, it’s a short drive to Crooked River Wines, where you can sip tasty reds and whites at the cellar door or sit down to local oysters followed by a grass-fed eye fillet in the restaurant.

In the other direction, to the south of Berry, Silos Estate is part winery, part restaurant and part alpaca farm. Settle in for rustic, modern Australian fare overlooking the vines, or head to the cellar door for a tasting. If you can't tear yourself away, there are even rooms to check in to across the property.

If you'd prefer to indulge in the arts, set your GPS for Bundanon. It's a slight detour but this art museum embedded in nature is well worth it. Dramatic architecture aside (the gallery is integrated into the landscape and rolling hills), the property is home to the Ian Boyd Studio and eco-friendly rooms for overnight stays, all enveloped by native bush webbed with walking trails and a wombat habitat.

Before you reach the Kiama coast, make your way to Saddleback Mountain Lookout to enjoy some perspective of the countryside. Along the way you’ll pass the region’s historic dry stonewalls, century-old structures encircling paddocks and pastures. Once you reach Saddleback’s top, soak up views over forest and farmland that extend to the Pacific Ocean.

For a closer look, tackle the Kiama Coastal Walk, or at least part of it. The full trail extends 20km from the Minnamurra River in the north to Gerringong in the south, but it’s easy to break your journey up to take in attractions like the Kiama Blowhole, where the sea spouts up to 30m into the air.

The natural beauty of the area has inspired creative types for decades, as you'll discover at the Old Fire Station Community Arts Centre. This hub is renowned throughout the Illawarra region not only for its rotating exhibitions showcasing local Kiama talent but also its colourful mascot: Daisy the Decorated Cow. When it’s time to refuel, visit The Hungry Monkey for burgers you won’t forget in a hurry – think lamb with caramelised onion, or panko-crumbed chicken with chipotle mayo.

Heading north, before you reach Lake Illawarra, veer off to the Shellharbour Airport to tour the HARS Aviation Museum, with its collection of flying and grounded aircraft recalling Australia’s aviation history.

Leaving the airport behind, follow the road around the west bank of Lake Illawarra, a popular nesting spot for myriad birds. The top of the waterway marks the start of Wollongong, replete with surf beaches and rock pools for swimming. Pause to peruse the Illawarra Museum, set in a heritage building and housing a collection of artefacts capturing the history (and characters) that shaped the region, from the 19th century to the present day.

Continue north along the coast, passing popular Austinmer Beach, where you can stay the night at Headlands Austinmer Beach. Here, apartments and studio rooms overlook the ocean and sand – a view that the light-filled restaurant also shares: the perfect perch for sundowners.

Before you beeline back to Sydney, drive along the Sea Cliff Bridge. This road snakes for 665m right out over the Pacific Ocean, waves crashing onto rocks below.

End your road trip at Symbio Wildlife Park, dedicated to the protection and rehabilitation of native and exotic animals. Meet kangaroos, koalas and reptiles, or book behind-the-scenes experiences to meet the species here.