Detour #312: Sydney Harbour to Bondi Beach The Longer Way, Australia
Photo Mel Nichols
It’s but four miles between two of Sydney’s legendary landmarks but you can make it a full day’s drive with the right Detours.
Everyone knows of Bondi Beach, right? It’s the most famous beach in the world.
But rather than drive directly there from central Sydney – it’s a bit over four miles as the crow flies – there’s a wondrous alternative. Instead, wind along Sydney Harbour’s treasure-packed southern shore to explore a secret Sydney. This route will take you past fabulous harbourside houses to tucked-away beaches, serene parks, secluded cafes, stylish restaurants and historic sites, all with dazzling vistas. This is waterside Sydney at its most interesting.
From downtown, head east through Kings Cross to pick up New South Head Road. Yes, there are attractions in the harbourside suburbs Darling Point and Point Piper but drive straight past and on to Rose Bay. As you approach it, your eye will be caught by what looks like a foreboding castle on a distant hill. Take note: you’re going to swing off the main road there into the warren of streets that run down to the water; they teem with some of Sydney’s most exclusive and expensive houses.
But first, go slowly through Rose Bay and look left to the water. There’ll probably be a seaplane taking off, winging lucky diners over the Northern Beaches to a stylish lunch at Pittwater, 30 miles up.
And if it were the 1930s, you’d see a majestic Short Empire flying boat bobbing at its moorings before slowly lifting off to take 30 or 40 privileged passengers on a luxurious multi-leg 14-day trip to England. Now, the site is marked by the Catalina restaurant, renowned for its seafood and the view from its dining terrace.
As you climb out of Rose Bay, you’ll appreciate why the thousands of runners slogging up the steep, bendy road in the annual City2Surf race call it Heartbreak Hill. At the top, abreast of that castle-like edifice dominating the skyline, turn left towards it on Vaucluse Road. It’s the Convent of the Sacred Heart, built in the 1880s from stone hand-chiselled on site, and subsequently today’s Kincoppal-Rose Bay School.
You’re now in the network of harbourside streets packed with some of Sydney’s most desirable houses, almost all of them glorying in spectacular views of the Harbour. Some are original and humble, some are grand, some are vast, fantastic modern designs that cost a fortune to build on multi-million dollar sites where the old dwelling was flattened. Driving past is endlessly fascinating – not just for the homes but the cornucopia of trees, shrubs and plants. Some of the streets are narrow and parking spaces tight, so it’s best to have a compact, manoeuvrable car like the Hyundai Kona HEV comfortably and quietly ferrying us.
About 600 metres down Vaucluse Road, dip left to Carrara Road and, if there’s a spot near its end, park there and walk down Tingara Avenue to the steps that’ll drop you the Hermitage Foreshore track. Many consider it Sydney Harbour’s finest walk. It’s an impeccably maintained one-mile path connecting five beaches where you can swim, picnic, or just soak up myriad magnificent views of the Harbour back to the Opera House and Bridge. Settle on the sandstone bluffs above the beaches for a perfect viewpoint to watch feverish yacht racing, particularly when the extraordinarily fast SailGP boats are here in February.
You’ll now be just a few metres from charming Milk Bay, a pretty, petite beach that’s perfect for a dip or picnic. From there the track winds up along the edge of the Strickland Estate to Nielsen Park. You could walk but since we’re driving, it’ll be best to retrieve your car and return to Vaucluse Road then turn north to Greycliffe Avenue, which is the parking area for Nielsen Park. It’s also where you’re most likely to find a parking spot to walk the whole length of the Hermitage Foreshore track back to Rose Bay, which I heartily recommend. The 325 bus will bring you back in 11 minutes.
Nielsen Park’s 20 hectares include original bush thousands of years old, giant fig and massive eucalyptus trees. Walk beneath them or picnic in their welcome shade. Kookaburras will be cackling – but watch out; they’re thieves and will dive to snatch food. You’ll be safe in the Federation-style The Nielsen café. And then there’s the golden beach, one of the Harbour’s most pleasant swimming spots: it’s called Shark Beach but don’t worry; it’s netted.
When you leave Nielsen Park, on Wentworth Road you’ll see Vaucluse House, an 1830s Gothic revival mansion reposing amid splendid gardens and parkland. A couple of hours there – entry is free – will transport you to 19th-century colonial life. This was the home of William Charles Wentworth, statesman, lawyer and explorer. In 1813, with Gregory Blaxland and William Lawson, he helped winkle out the route through the Blue Mountains that opened up the plains west of Sydney to settlers. He’s entombed a little further on in the Wentworth Mausoleum, which peeps down through the trees to Chapel Road. You can walk in to pay homage if you wish.
On now to Watsons Bay, a historic harbourside suburb with a beach almost as famous as Bondi. For many visitors, the ferry ride from downtown Sydney’s Circular Quay is – rightly – a must-do day trip. Swimming (there’s a netted area), soaking up and photographing stunning views, and dipping into Sydney’s earliest history are all on the agenda – not to mention a leisurely seafood meal at the famous Doyle’s on the Beach Restaurant. The South Head Heritage Trail leads to the dramatic cliffs of The Gap and South Head, where the red and white Hornby Lighthouse signals the entrance to Sydney Harbour.
From here, walk or drive the short distance north past quaint old cottages to Camp Cove, another serene beach of great historical importance. Here, Captain Arthur Phillip and eight or nine men pulled up their whaleboat to camp overnight on January 21 1788. They’d left windswept and arid Botany Bay to scout north for a better location for Australia’s first settlement. Next day as they explored Port Jackson (Sydney Harbour) their eyes must have popped as they discovered what Phillip called “without exception the finest harbour in the world.” Eight miles up, where Circular Quay now is, he pinpointed the perfect bay. On January 26 1788 he returned with all the First Fleet’s 11 ships and 1,400 people and raised the British flag at what he called Sydney Cove, thus founding the colony of New South Wales. As rock paintings and shell middens attested, Camp Cove had for millennia been a fishing and camping site for the Gadigal people; today it blends rich Aboriginal and colonial history.
Now comes an absolute must: from the end of Cliff Street, pick up the South Head Heritage Trail and ogle spell-binding views as you walk the loop above Lady Bay Beach out past the Lightkeepers’ Cottages to red-and-white striped Hornby Lighthouse, which has guarded the southern entrance bluff of Sydney Harbour since 1858. Linger and watch ocean liners slipping in and out, and admire views all the way back up the Harbour and across to Many and North Head, 1.2 miles away.
Time now to turn south, following the Pacific Coast bluffs, to Bondi. Where Cliff Street becomes Military Road, perhaps pause for 15 minutes to walk out to The Gap for more views of spectacular cliffs and rock formations. If it’s a hot day – it was 32deg C the last time I did this drive – you’ll be pleased to slip back into a car with air con as good as the Kona’s.
Follow Old South Head Road on past Macquarie Lighthouse, Australia’s oldest lighthouse. In 1791, just three years after the First Fleet’s arrival, a flagstaff and fire beacon were erected here to assist ships into Port Jackson. Governor Lachlan Macquarie replaced it in 1818 with a proper lighthouse using whale oil lamps with reflectors. Today’s elegant white tower took over in 1883.
A bit further on, turn left onto Military Road and scoot behind the clifftops to Bondi. Stop at the Dudley Page Reserve for a majestic view of Sydney. Shortly, as you come down the hill into North Bondi, the sight of the world’s most famous beach will unfold ahead of you. There you can begin another adventure – having enjoyed the memory-searing glories of Sydney Harbour along the way.
ROADBOOK
CLASS: Ocean Drive
NAME: The Longer Way to Bondi
ROUTE: Sydney to Bondi Beach
COUNTRY: AUSTRALIA
Distance: 14 Miles
It’s but four miles between two of Sydney’s legendary landmarks but you can make it a full day’s drive with the right Detours.