Uniting beach and forests, wineries and breweries, a road trip from Sydney along the South Coast of New South Wales and back through the Southern Highlands offers a snapshot of much that is great in the state. Bring your appetite — for great food and adventure — and prepare for days of exploration from Kiama to Jervis Bay then up to Berrima and Bowral. 

Sydney to Kiama  

The road trip from Sydney to Kiama takes you along 140km Grand Pacific Drive, a scenic stretch of coastline through rainforest, national parkland, charming seaside villages, remote beaches and a snaking bridge taking you over the Pacific Ocean.  

Driving through Royal National Park, the oldest of national park in the country, you’ll soon reach Bald Hill, a world-renowned jump-off point for hang-gliders and paragliders. Motor across the Sea Cliff Bridge, which twists for 655m over the ocean and around the escarpment, through Wollongong and on to Kiama.  

This coastal cove is known for its blowhole and clifftop Coast Walk, but it’s also a standout destination for food and wine. Once you’ve worked up an appetite, head to The Hungry Monkey for bulging burgers and shakes best enjoyed in the alfresco dining area.  

Gerringong and Jervis Bay 

It’s a short drive 10km south from Kiama to Gerringong, perched on a dramatic headland and with access to a swathe of beaches for both swimming and surfing. Reason enough to visit is the father-and-son-operated Stoic Brewing, which makes everything from creamy oat IPA to cloudy apple cider on site.  

Buckle up for the 70km drive south to Jervis Bay, a part of the state where whiter-than-white sand beaches cradle a protected marine reserve where you’ll likely spot resident dolphins and whales (between May and November). Jump aboard an expedition to spot them with Jervis Bay Wild, Discover Jervis Bay or Dolphin Watch Cruises, all departing from the town of Huskisson.  

Worked up a thirst? Meet some of Jervis Bay’s new-wave beer makers at Jervis Bay Brewing Co., where you can sip everything from a fruity raspberry wheat beer to an intense dark lager paired with bites from a rotating roster of food trucks. Stay overnight in a coastal-inspired cottage at Bangalay Luxury Villas, which has a restaurant worth travelling the state for. The menu at the in-house Bangalay Dining spotlights native and local produce, including Sydney rock oysters, kangaroo, finger lime and wattleseed.

Jervis Bay to Mollymook 

More molluscs await at Jim Wild’s Oysters, a family-owned establishment where you can order Pacific and rock oysters to be delivered, freshly shucked, to your alfresco table overlooking the Crookhaven River.  

Venture south for 75km to Cupitt’s Estate winery on the outskirts of Milton, a town lined with ornate 19th-century buildings that are home to galleries and gift shops, for lunch. The property not only makes delicious chardonnay and merlot, among other varietals, but also has a brewery and fromagerie beside the restaurant — which features a menu of farm-fresh dishes.  

When it’s time to rest your head, check in to Bannisters by the Sea, a 10-minute drive southeast in Mollymook. Design-driven rooms here have a nautical theme, which carries through to the signature restaurant overseen by celebrity chef Rick Stein — expect seafood done to perfection 

Around Berrima 

Set off for the Southern Highlands, 130km to the northwest, with its cool-climate wines, grand seasonal gardens and charming colonial towns. En route, pause at Fitzroy Falls, where water tumbles 80 metres from the escarpment into a lush valley below.  

Then prepare to taste the region at PepperGreen Estate in the Georgian village of Berrima. Housed in a former antiques store, the cellar door and restaurant today offer wine and olive oil tastings as well as tantalising meals.  

Meanwhile, seasonal beers are the order of the day at Southern Highlands Brewing Co., a 20-minute drive southeast in Moss Vale. Order a red ale or porter in the Taphouse restaurant, and sip with pastas and pizzas on the side.  

On your way back to Berrima, Tractorless Vineyard offers immersive tours that not only offer a taste of biodynamic wines, but also let you discover the farming principles behind this style of grape growing — you can also meet the resident sheep.  

As evening falls, enjoy modern Australian cuisine at Berrima’s Eschalot, where chef-owner Matthew Roberts showcases the region’s produce in dishes like dry-aged sweet potato with cashew cream, wild-rice dukkah and pickled carrots from Brillig farm. Then bed down for in a heritage room above the stables at The Loch estate, a working farm where style and sustainability go hand in hand. If you’re there for a Sunday, book in for the weekly feast enjoyed amid lush gardens. Or check in to Berrima Vault House (opening May 2021), a boutique hotel, members’ club and lifestyle store in a historic building hand-made by convicts in 1844.  

Southern Highlands and Kangaroo Valley 

Adventure awaits with a day of wine tasting, paddling and sampling local produce on the Canoes, Cool Climate Wines & Canapés tour with Wild Food Adventures. It’s around 50km southeast to the Kangaroo Valley, where you’ll work up an appetite canoeing across a lake before being served cool-climate wines and canapés. The next part of the tour is lunch at one of two innovative restaurants: Birch in Moss Vale or Mount Ashby Estate, which takes local produce and gives it a French twist. In the afternoon, the tour moves to Cherry Tree Hill Winery — try the fumé blanc, fermented in French oak for 13 months.  

Bowral and Mittagong  

It’s just a 10-minute drive east from Berrima to Bowral, a gorgeous historic town with handsome manor houses all wrapped in leafy gardens and parks. Bowral is also known for its excellent antiques and homewares shopping — Dirty Janes is an emporium selling everything from cane furniture to old signage and taxidermy, while Barbaras Storehouse has affordable outdoor furniture, assorted ceramics, baskets, kitchenware and many other treasures for those with a keen eye.  

For a leisurely lunch, Harry’s on Green Lane serves rustic share plates in a plantation-chic room lined with bookshelves brimming with plants, travel bric-a-brac and well-worn novels. Then as you journey back to Sydney, pop in to Eden Brewery in Mittagong (a 10-minute drive north) for bold craft beers and a community vibe — the team donates 10 per cent of profits to Oxfam to provide clean drinking water to those in need.