Who knew Sydney had a shy side? Di Webster spends three days on its world-famous harbour and discovers a city with genuine soul.

“Drive… drive…” Whoosh. “Drive… drive …” Whoosh. What is going on? I open my eyes and take a second to get my bearings. Early morning light filters in through the rainspattered hatch above the bed and a cool breeze drifts in through an oblong porthole beside my pillow. I peer out as a rowing pair powers by, their cheeks pink, ponytails swinging, oars carving into the satin water in perfect sync.

“Stroke… Stroke…”

I’m anchored in secluded Sugarloaf Bay off the southern tip of Garigal National Park in Sydney’s Middle Harbour, just metres from deserted Flat Rock Beach. There’s sand to the left, rocks to the right and a waterfall that, thanks to a couple of days of rain, has erupted from the escarpment. Birdsong combines with the gentle drizzle like a meditation video. “I wanted to shush the rowers so you could sleep,” jokes crew member Cameron MacDonald as I emerge from my cabin on MV Felix, the vessel that’s been transporting my husband, Steve, and I – literally and spiritually – around a Sydney you don’t see on billboards. It’s a story of secret urban beaches, coves so pretty and quiet they could be light-years from a city and wild headlands that keep their fascinating history hidden in plain sight.

While it’d be easy not to venture far from this 58-foot Salthouse cruiser with its paddleboards, floating foam island, inflatable pool pontoon, glorious food and much champagne, this iconic body of water needs context. Seeing the harbour from Sydney is almost a cliché. Seeing Sydney from the harbour is to develop a new appreciation of this mercurial city – at once fast and flashy, low-key and soulful.

Berry Island Reserve at Wollstonecraft, NSW

Which may be why, two hours after freeing the ropes from King Street Wharf, skipper David Higgins is manoeuvring his boat into the visitor marina at the southern end of Cockatoo Island, sending squawking seagulls into the grey yonder. Soft rain smudges the harsh edges of industry past and present – soot-covered old factories, rusty tin roofs, a featureless admin block – and a skyline punctured by brick chimneys and cranes.

I’m not going to lie; it feels like an odd place to kick off a voyage on a global showpiece declared “without exception the finest Harbour in the World” by Captain Arthur Phillip, commander of the First Fleet, in 1788, and endorsed by no end of real-estate gazillionaires since.

But as we’re about to discover, there’s no better place to understand modern Sydney than this industrial lump of sandstone. “It is where the rivers join and is in the middle of where the sun rises and sets over the harbour,” wrote Isabel Coe, leader of an Aboriginal rights group that set up a tent embassy on the island in 2000 in an ultimately unsuccessful bid to gain native title. “This would have been a very sacred site.” Though, sadly, no evidence of that early First Nations presence remains, Cockatoo Island, which sits in the Parramatta River between posh Woolwich and pub-peppered Balmain, holds the colonial chronology of Sydney Harbour like a thumb drive: the remains of a grim and forbidding penal establishment, the infrastructure that drove a powerhouse of ship building and repair, gracious sandstone homes for the island’s administrators and, today, luxury launches and sailing boats moored in inlets and stacked in warehouses waiting for their well-heeled owners.

And that’s the story of Sydney right there – ancient wonderland, colonial prison, industrial work station and indulgent pleasure zone. Today, thanks to the weather, we have the old tunnels, the green grass and the grim and glamorous history all to ourselves. “You okay?” shouts a first-aid buggy driver, spotting two drenched figures striding purposefully along the dock. “We’re fine!” we shout. At the old prison, we trail our hands across cold sandstone walls that once housed as many as 500 men – “the worst of the worst”. We walk a carpet of wet jacaranda petals to a grand Federation home and marvel at the views from its lawn tennis court. I’m drawn into yet another stone building by a tinny recording of Advance Australia Fair to find a 1930s newsreel about the docks flickering on the wall. It’s just me and 100 years of heritage in here and it’s compellingly spooky.

“We’ve got paddleboards if you feel like getting in the water,” skipper Higgins says later, after we drop anchor off Queens Beach, a sublime little smile of sand on the harbour, at the bottom of a cliff in Vaucluse. Like the many hidden treasures Higgins is turning up, we had no idea this beach existed (and Steve grew up in the area!). I decline the SUP, feeling no need to break down the reasons (20 per cent not hot enough – the weather, I’m talking about – 80 per cent lack of core strength). I’m happy to relax with a cool drink and watch frolicking dogs, intense joggers pounding the two kilometre Hermitage Foreshore Walk and a hillside waterfall that I swear starts gushing while we’re taking in the scene, as though there’s a props master concealed in the foliage.

Paddleboarding off Queens Beach in Vaucluse, NSW

Besides, there’s plenty of exercise ahead for us. We meet Alan Toner outside HMAS Penguin, a naval base that sprawls across Middle Head, one of the harbour’s seven headlands and home to some of the best views in town – from the ritzy eastern suburbs right across to laid-back Manly. An army veteran who served in Iraq and East Timor, Toner now runs EcoWalks Tours, which offers a remarkable guided journey through Sydney Harbour National Park to fortifications that guarded the waterway from soon after European settlement through to World War II, with intriguing elements (and stories to match) from the Vietnam War era. Before we set off, standing on Middle Harbour Oval, Toner gives a moving acknowledgement to the Borogegal and Cammeraygal peoples, traditional custodians of Gubbuh Gubbuh (Middle Head) peninsula. It’s quite a moment, made more poignant by dozens of little birds that dart around us, skimming the grass like turbo-charged paper planes. “What are they?” I ask Toner later. “They are,” he says, almost anticipating the question, “welcome swallows.”

Steve and I have walked this track many times, never noticing the native fuchsia, flannel flowers and Sydney golden wattle that Toner points out, or realising how the blue flax lily with its vibrant purple berries was useful to First Nations peoples. We’ve also clambered across the gun emplacements that dot the cliff face not knowing the stories behind them. After leaving the army, Toner became a geography teacher with a forensic interest in military history, a passion for the environment and a knack for sharing his vast knowledge while making you feel like the smartest person on the bush track. “That’s right, Di!” he says in response to an observation. “Correct, Steve!” It’s as if you’re seeing the headland in colour for the first time.

Between stops, we dine at harbourside eateries, both celebrated and emergingly fabulous, the boat arrival adding an element of glamour that an Uber can’t match. On the last night we pull up at Flat Rock Beach, where, as if the setting isn’t dreamy enough, we welcome aboard Raphael Matet, owner of boutique outfit French Fare Catering. He whips up an exquisite meal (ocean trout ceviche, panfried snapper fillet, lamb with a pine nut and thyme crust, mocha profiteroles and a pear and almond tart) in the small galley. “This is my happy place,” Matet tells us as he snips micro herbs from the row of pots he’d loaded onto the boat’s dinghy and unpacked on the bench, before disappearing back into the night. Did that really just happen?

The next morning, I wake to the birdsong, the gentle drizzle, the scent of eucalypts, the rhythmic rowers. Sydney is renowned for glitter. On its harbour, I believe we’ve found gold.

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Harbourside dining


This always-busy, consistently excellent Rose Bay waterfront fine-diner is as much a feature of Sydney Harbour as the seaplanes that have landed in the bay since 1938. Starched white tablecloths speak to the restaurant’s smart service but also belie its buzzy community vibe. With floorto- ceiling windows framing the views, there are no bad tables but a prized pozzie on the balcony with the sun shining, yachts bobbing and market-fresh fish on the table is Sydney on a plate.

Betel Leaf @ Bathers’

It’s way past time to drag the “good view = bad food” trope to the trash. Occupying the top floor of the acclaimed Bathers’ Pavilion on glamorous Balmoral Beach, Betel Leaf not only has a stunning outlook over the sand and out to the heads but also boasts one of the city’s finest Thai chefs (Sailors Thai alum Ty Bellingham). Inside or out on the terrace – it’s up to you and the weather. Just do not proceed to a main course until you’ve tasted the Tasmanian scallops with green nahm jim.

The Boathouse Rose Bay

The new kid on the burgeoning Boathouse Group block, this sunbathed kiosk and restaurant sits on the marina at Rose Bay doing exactly what any smart establishment in this location should: offering tasty, hungerbusting fare for yachties and walk-ins downstairs and taking a more refined, seafood-focused table-service approach upstairs. Swing by the kiosk for brekkie – fresh air, sunshine and smoked salmon fritters.

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Image credit: Con Poulos

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