Haven to Highlands

Stop and stretch your legs at Bald Hill, one of the best coastal hang gliding locations in the world, then motor along the Sea Cliff Bridge, which extends over the ocean around the escarpment. In Kiama, eat at The Hungry Monkey – there’s a range of classic burgers and super-sized salads. Stroll a short section of the spectacular Kiama Coastal Walk after lunch then head to Gerringong to visit the father-and-son-operated Stoic Brewing and try one of their handcrafted beers brewed on site.

Make your way south to Jervis Bay to embark on a dolphin cruise with Jervis Bay Wild or Dolphin Watch (both departing from Huskisson). Back on land, meet some of Jervis Bay’s new beer makers: Jervis Bay Brewing create beers to complement the area’s sunny skies (and different food trucks park in the brewpub every day); Flamin’ Galah Brewing Co. is run by a husband-and-wife team that offer growlers and six-packs to takeaway (with a brewpub in the works). Stay overnight in a coastal-luxe villa at Bangalay. Dine in their renowned on-site restaurant, with native, local ingredients gracing the menu.

Meet Jim and his family at Jim Wild’s oysters and sample his top-notch Sydney Rock and Pacific oysters. Venture to Cupitt’s Winery near Milton for lunch. Sip distinctive wines made by the Cupitt family and dine on meals crafted from produce grown on the farm. After lunch, it’s worth exploring the streets of Milton, lined with ornate 19th century buildings, galleries and gift shops. That evening, check into Bannisters by the Sea for a luxurious stay and dinner at Rick Stein’s signature restaurant with incredibly fresh seafood and sweeping ocean views.

Along the route, pause at Fitzroy Falls, where water falls 80 metres to the lush valley below. In Berrima, visit PepperGreen Estate Cellar Door housed in a former antique store, for wine and olive oil tastings and a cheese board. Visit Southern Highlands Brewing Co. to try their traditional and seasonal pours on tap, and stay for lunch at their tap house in the historic Toose's building on Argyle Street. Or go to Tractorless Vineyard for sustainable wines and the unique Tour, Tasting, Meet Our Woolly Workers experience – the vineyard’s sheep are an integral part of the biodynamic practices.

As evening falls, arrive at eatery Eschalot with its hushed hues, seamless service and masterly menu with delicate seasonal ingredients. Bed down for the next two nights in a heritage room above the stables at The Loch estate; each room has an ensuite, luxurious living space and pretty rural views.

Deep in the Kangaroo Valley, on a freshwater lake, you’ll paddle a canoe then stop to sip local sparkling wine and eat native canapés. The next part of the tour is lunch at one of the region's most innovative restaurants: Mt Ashby Estate Vineyard. Here, local produce is given the French treatment, with twice-cooked gruyère soufflé and confit duck among other favourites. In the afternoon, the tour moves to Cherry Tree Hill Winery – try the fume blanc, fermented in French oak for 13 months.

The town is known for its excellent antique shopping – Dirty Janes is an emporium of more than 60 shops with everything from cane furniture to old signage and taxidermy. Barbara’s 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. As you traverse back to Sydney, pop into Eden Brewery in Mittagong for bold craft beers and a community vibe; the team donate 10 per cent of profits to Oxfam to provide clean drinking water to those in need.