The lush Southern Highlands of NSW offer endless opportunities for exploration. In recent times the once-traditional farming region has become a hotspot for forward-thinking wineries, great food, and a collection of oddball but interesting shopping options.

In partnership with the Jeep Grand Cherokee, here’s how to hit the road and unearth some of the area’s best-kept secrets.

SATURDAY

Drive
The Southern Highlands of NSW are just a 90-minute drive south of Sydney. And it couldn’t be easier. Leave town on the M5, transfer to the Hume and it will take you all the way. Comprised of Bowral, Berrima, Moss Vale, Mittagong, and Bundanoon, you’ll be greeted by fresh air, a relaxed pace, and if you’re there in the spring, the blossoming cherry trees.

It’s also a burgeoning wine region. With a 700-metre elevation, the grapes that grow here are predominantly cooler-climate varietals and have produced some award-winning pinot noir, chardonnay and riesling. The attraction of visiting wineries is as much about the landscape as the produce. Green rolling hills, gravel tracks, dirt roads, and undulating highways makes for attractive travel.

Lunch – Bendooley Estate
Just past Mittagong, take a left on to the Old Hume Highway and make a lunch stop at Bendooley Estate. The 200-acre property boasts beautiful gardens, a cellar door, and a lake for strolling around. But inside? A specialised antique bookstore with more than 3000 titles.

Peruse some of the latter over a restaurant lunch menu that includes linguine with blue swimmer crab, a selection of wood-fired pizzas and if you’ve skipped breakfast, the Bendooley Burger – 200-gram ground prime beef, zucchini pickle, house-smoked bacon, cheddar, aioli and bois boudran sauce and chips. Maybe save that lake stroll for after lunch.

Adventure – Hit the Trails
Your 10-minute drive to Joadja Winery is lined with tall gums, beautiful green hilltops and farmlands. Joadja is the oldest winery in the region having first planted grapes here in 1983. Original owners Kim and Francis Moginie are heralded as the wine pioneers of the area, and only last year handed the reins to Matthew Toomey and Siobhan Maloy.

Sure the wine is delicious but the best thing about the property? It’s open to the public for self-guided tours, meaning you can explore the lush grounds at will.

From there bounce to Kells Creek Road, 10 minutes away, and Tertini Winery. The cellar door experience here is two-fold: if cold you can nestle in by the fire, if warm sit outside surrounded by tall eucalypts. Either way you’ll receive a complimentary cheese platter.

Current winemaker-in-chief, Jonathan Holgate, produces an incredible array of award-winning wines, and while the specialities here are pinot noir and riesling, the rare Italian arneis are worth investigating.

A 20 minute drive south on the Hume brings you to Eling Forest Estate, home of the Tractorless Vineyard winery and cellar door. The grounds here sport an 1840s homestead that has been transformed into accommodation overlooking a lake, as well as a beautiful field of cherry blossoms.

Winemaker Mark Bourne and his team have been observing biodynamic techniques since their inception in 1988 and aim to provide a more long term sustainably balanced and diverse farming system that can continue to produce award-winning wines. Hint: One of their specialities is bubbly and on weekends they offer tours to witness the making of a bottle of champagne.

Dinner – Eschalot
Time to take a seat. Head to Berrima, and settle in at Eschalot. Housed in a heritage building from 1852, and surrounded by gardens and greenhouses growing many of the ingredients you’ll find on the plate, this fine dining restaurant is a major award-winner for its European-inspired fare.

You can choose between having three, four or eight dishes, and the meals are seasonal, adventurous, and delicately balanced – think goat’s cheese soufflé, Wagyu "pot au feu", cabbage cream, baby white veg, marrow, puffed tendon, roasted cabbage juice; and roasted Snapper, crust of seaweed, smoked oyster cream, young fennel, kaffir lime kosho, leek sauce and lime oil.

Meander through the gardens here and you’ll see the Berrima Courthouse and Gaol, and across the road Eschalot owner Richard Kemp’s second venue, E2 Events, which often hosts local musicians in its underground event space on weekends.

Stay at Biota
Head back to Bowral and unpack your overnight bags at Biota. With 12 rooms attached to their own dining-experience, Biota offers a boutique hotel experience that can be described as “rustic luxury.” The minimally decorated, white-walled rooms are appointed with tea and coffee, botanical bathroom supplies and breakfast is included. Sleeping in sounds attractive after a long day exploring, but hot tip: watching the sunrise over Bowral from Oxley Hill Lookout is pretty special.

SUNDAY

Brunch at Ludo
Biota’s complimentary breakfast does compel, but you’ll need a top-up before hitting the road again. Ludo cafe on Station Street in Bowral will provide. You won’t be able to miss the cute light-blue weatherboard cottage sitting there on the main strip, and once inside you’ll be surprised at how much space there is, with an extended outdoor area at the back. Must-try options include the ocean trout bruschetta and the pancakes.

Adventure – Antiquing at Dirty Jane's Emporium and Antique Market
Before you throw yourself back in the direction of the city, one last afternoon for exploration. There are plenty of antique stores in the Southern Highlands, but at Dirty Jane's Emporium and Antique Market is a destination in itself. Whether you’re into homewares and clothes, or collecting old cameras, books, or instruments, Dirty Jane’s has you covered. With a range of tea rooms, gardens, potting sheds, florists, and stalls full of both old and new on the premises, it’s easy to lose track of time here.

Once you’re stocked up, jump back on the Hume Highway and head towards Sydney. Adventure complete.

This article is produced by Broadsheet in partnership with the new Jeep Grand Cherokee, the perfect way to take on the ultimate weekend adventure in style.