Let's go! With the shackles coming off, the weather warming and daylight savings stretching out the day, it's time to hit the road. This loop drive south from Sydney could be done in a day, but that's like rushing a great meal. Make it a lingering journey over two or three nights and rediscover a gorgeous part of the state. Scooting south from Sydney via the M1, turn left onto Lawrence Hargrave Drive for a corkscrew journey to Stanwell Park, the first coastal town south of the Royal National Park. Stanwell Park is a barefoot, blue-water jewel with a wondrous beach. Break out your swimmers and hit the surf if the flags are up, then follow it with a comfort-food stop at the Loaf cafe.
Resuming its southern fling, Lawrence Hargrave Drive twists through coastal villages north of Wollongong, skittering out over the ocean at Sea Cliff Bridge.
Past Wollongong and south of Kiama, the highway turns snake-like as it girdles the foothills of the coastal escarpment then rushes downhill where a left turn takes you to Gerringong. Pass through the town and at Gerroa, just before the Crooked River Bridge, a left turn at Riverleigh Avenue delivers you to the Blue Swimmer at Seahaven, a local hero with a menu strong on seafood to go with the maritime views.
Continue along Crooked River Road, then take a right onto Beach Road, heading to Berry. Marinated in green pastures that rise behind the town to form a rippling tapestry woven with forest, Berry is style central in this part of the world, furnished with a sourdough bakery, cafes dishing out urban-strength espresso, and real estate windows that inspire dreams of a countrified existence with a tennis court and a couple of horses next to a rainforest-rimmed creek.
From Berry, Kangaroo Valley Road ambles through leafy back streets but soon turns feral, squeezing in its sides and squirting up timbered hillsides before levelling out in pastures before the village of Kangaroo Valley.
Ringed with evergreen meadows, overshadowed by stone-sided hills that rise sheer from the valley, Kangaroo Valley is ripe with promise, yet the sheer lovable dagginess of the town saves it. Its pillars rest in the soil, its feet rest happily in muddy boots, and the weekend retreats of the Sydney crowd are tucked out of sight at a discreet distance. Stretch your legs, and don't miss the General Cafe, whose mantra is "handmade, local, fresh and sustainable".
One of the prettiest drives in the area, Upper Kangaroo River Road wanders through farmland along the riverbank, becoming wilder as it infiltrates the forest. Past Scotts Road, where a sign points to the Yarrawa Estate Winery, the road splashes across a couple of infant creeks to end at Flat Rock River Rapids, a honeyed spot for a picnic, especially for kids.
Bendeela campground is next to the Kangaroo River. Photo: Getty Images
The canoe hire outlet at Hampden Bridge can set you up with the essentials for a dawdling three-hour paddle down the Kangaroo River, through green tunnels with water dragons for company, the current doing half the work. Lower down, there's a tricky squeeze between boulders where the water narrows and quickens – get it wrong and the river will tip you out. But even if you do stay dry, strip down for a swim well before you get to the haul-out spot at the Bendeela campground.
Beyond Hampden Bridge, the highway leaves the valley and ties itself into knots as it races up the escarpment to the heights of the Southern Highlands. A right turn just beyond Fitzroy Falls leads to the hamlet of Burrawang. This was one of the earliest settlements in the region, but later in the 18th century the village was bypassed by the Illawarra Highway and the railway line and Burrawang fell into a coma. Today, wide awake, it's a time capsule with a treasury of historic architecture and a popular bolthole for Sydneysiders. If it's close to lunch time, the Burrawang Village Hotel does great pub meals.
Cradled between Mount Gibraltar and the curving Wingecarribee River, Bowral is the lifestyle capital of the Southern Highlands. More than a century ago, the town's leading citizens began a tree-planting program, and their legacy lies in Bowral's glorious avenues of mature, deciduous trees and public and private gardens.
Endowed with an ever-expanding array of small food producers, farm-gate stalls, olive groves and pioneering chefs who delight in the natural bounty of the region, the Southern Highlands is an exciting destination for food and wine lovers. The list of small producers includes Pecora Dairy, an artisan sheep milk dairy and cheesery near Robertson; Redleaf Farm, specialising in ethically raised meats from saddleback pigs and purebred Scottish highland cattle, and Cuttaway Creek near Mittagong, the home of jams, sauces and vinegars made from berries grown on the farm.
Bowral Produce Store has a wide range of antiques. Photo: @mount_ashby_estate/Instagram
This area is also one of Australia's newest wine-growing regions, featuring over 60 vineyards that specialise in cool-climate varieties. Download the wine trail map from the Visit Southern Highlands website and you're away. Joadja Estate, near Berrima, is the oldest vineyard and winery, planted to slow-ripening, cool-climate varieties that produce wines of intense flavour, character and complexity. Mount Ashby Estate is a boutique vineyard located between Moss Vale and Fitzroy Falls with a courtyard cafe, perfect for warm-weather lunches. The cellar door area includes the relocated Bowral Produce Store, now the home of Mount Ashby Estate Antiques. Southern Highland Winery near Sutton Forest is one of the region's most striking wineries, with a restaurant that takes its cues from regional Italian cuisine.
The Southern Highlands has also developed into a five-star dining destination, but book well ahead. Names such as Paste, Centennial Vineyards Restaurant, Onesta Cucina and Bistro Sociale are currently in post-lockdown recovery. Make any one of them the final stop on your journey and you'll have happy memories lasting all the way back to Sydney.
Mount Ashby Estate is a boutique vineyard and cafe. Photo: @mount_ashby_estate/Instagram