Experience the beauty of Sydney Harbour anew on the walking trail that links the city's two most famous beaches: Bondi and Manly.

Do you need a shower?

Asks a spritely grey-haired woman, smiling and offering me the hose she’s using to water her garden. “I thought you’d never ask,” I reply, pausing to wipe the sweat that’s charging down my face. Point Piper, in Sydney’s east, doesn’t see a lot of hikers. Residents glide in and out of this harbourside enclave by boat or luxury SUV. I’m surprised the appearance of a sweaty man with walking poles hasn’t been reported to the authorities. Perhaps it has. But the locals have no cause for alarm as I’ve innocently stopped about a quarter of the way through the Bondi to Manly Walk (B2M), an 80-kilometre trail that winds between the NSW capital’s two best-known beaches. It claims to be “the greatest city walk in the world”.

Mansions at Point Piper, Sydney

Unlike a wilderness trek, most sections of the B2M can be accessed by public transport, which means, as a local, I could have chipped away at it over weeks or even months. But I wanted a challenge so I settled on a three and-a-half-day itinerary with stops at four luxe lodgings along the way, including QT Bondi, the InterContinental Sydney Double Bay, the Wildlife Retreat at Taronga Zoo and Manly’s Q Station.

As well as self-guided treks, using the app and track notes found on the B2M website, you can also contact the organisers and have them sort out the logistics, from booking hotels and restaurants to transferring your luggage, while you saunter from one gorgeous spot to another.

Bondi Beach, Sydney

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My ambitious schedule means I’ll hike about 20 kilometres each day, carrying all my gear. Hence I’m toting not-entirelynecessary walking poles and wearing infrequently used hiking boots (#mistake). I start in Bondi and it says a lot about the suburb’s colourful cast of characters that no-one bats an eyelid as I click-clack along the promenade looking like I’m headed for the Himalaya. I walk from Bondi to South Head, skirting the dramatic 80 metre-high sandstone cliffs. When I pause at a viewpoint overlooking Diamond Bay Reserve in Vaucluse, I’m joined by a tradesman who’s pulled out his phone to take a photo of the ocean crashing against the rugged coastline. “Look how blue the water is,” says the tradie. “Just spectacular!”

After looping around South Head, the route follows the harbour’s southern foreshore towards the Sydney Opera House then hops over the Harbour Bridge and traces the northern shore from Kirribilli to Manly Beach. Along the way, I navigate a captivating variety of terrains. One minute I’m strolling through a manicured reserve (like Neutral Bay’s Anderson Park, which Sir Charles Kingsford Smith used as a runway in 1934), the next I’m trudging along a pristine white-sand beach (Sirius Cove in Mosman, named after HMS Sirius, the flagship of the First Fleet). Even when I’m forced to zigzag through exclusive harbourside suburbs, I frequently stumble upon hidden lookouts or am plunged into an unexpected pocket of bush.

Given Sydney’s obsession with waterfront real estate, it’s a miracle that so much of the foreshore is accessible to the public. One beguiling section is the Hermitage Foreshore Track, a 1.8-kilometre stretch of native bushland in Vaucluse. As I walk along a boardwalk flanked by dense thickets of wattle and grass trees, with the sound of cicadas buzzing in my ears, it’s easy to forget I’m in the city.

Along the way I’m offered glimpses of where I’ve come from and where I’m headed – which is either motivating or  demoralising, depending on how I’m feeling. And, surprisingly, I’m feeling quite enthusiastic until the afternoon of day one, when I discover my hiking boots have given me a blister. The staff at the InterContinental aren’t fazed by the man who winces as he limps into the lobby. After fashioning a MacGyver-style pressure-relief system from a foam insole, I’m back in the game.

As I continue, I take the opportunity to slow down and observe the everyday vignettes that make Sydney so Sydney. I watch schoolkids launching kayaks from Balmoral Beach, teenagers learning to sail at Rose Bay and families buying Magnums from an ice-cream boat at Clontarf Beach. I find myself in suburbs I’ve never visited on foot, where the mansions have names rather than numbers and even the carports have million-dollar views. I discover that the more desirable the suburb, the more steps I need to climb to reach it. In fact, in Mosman, on the Lower North Shore, I become so accustomed to climbing endless flights of stairs that I inadvertently trespass on someone’s back garden.

Of course, the greatest reward for walking all day is that you can justify eating all night. Some of my best food moments include succulent lamb shoulder at the homey Sean’s in Bondi; a perfectly cooked Wagyu steak at Me-Gal, the fabulous restaurant at Taronga Zoo’s Wildlife Retreat; and a delicious tarragonbutter-drenched snapper at stylish Manly Greenhouse.

By the time I reach Q Station on day three, I assume I’ve seen all the highlights. But the B2M has one more surprise up its sleeve: North Head Sanctuary. On my final morning of the journey, I join walkers, trail runners and mountain bikers on the fern-lined tracks of this delightful stretch of elevated bushland.

From here, all that remains is a careful descent to Shelly Beach and a stroll past Cabbage Tree Bay Aquatic Reserve to Manly’s spectacular ocean beach. There’s no fanfare, no champagne and – disappointingly – no sign, just a quiet feeling of accomplishment and a pang of sadness that it’s over. Another upside? On the ferry trip back to Circular Quay in the CBD, I can proudly name every bay, beach and peninsula that appears in our wake.

Shelly Beach, Manly, Sydney

Choose your own adventure

While the B2M follows a set route, how you tackle it and the activities and tours you do along the way are entirely up to you. Here are some pit stops to try...

Active types can start their B2M adventure with a surf lesson at Bondi with Let’s Go Surfing. Further along in your journey, explore Middle Harbour by kayak with Sydney Harbour Kayaks, before ending with a two-wheeled tour of Manly with Manly Bikes.

Scuba Diving, Shelly Beach, Sydney

To learn more about Bondi’s Indigenous heritage, join local Elder Walangari Karntawarra for a walking tour. You can explore The Rocks with Dreamtime Southern X or discover how the Gadigal people used the region’s native plants on an Aboriginal Cultural Tour of the Royal Botanic Garden.

Chowder Bay, Sydney

The B2M trail takes art-lovers past a slew of galleries, including Artspace in Woolloomooloo, the Museum of Contemporary Art Australia at Circular Quay and the Manly Art Gallery & Museum on the West Esplanade. Detour to visit Bondi’s Aquabumps and the Art Gallery of NSW in the CBD.

It’s hard to miss the military remnants scattered along Sydney’s clifftops but to explore them properly you’ll need to take a guided tour with the Harbour Trust. Options include Sub Base Platypus, a former submarine base in North Sydney; North Fort’s network of gun emplacements; and the tunnels of Georges Heights at Headland Park, Mosman. 

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