Harbour Clifftops & Bushland Bays: A 6-Day Sydney Itinerary for Coastal Hikes, Hidden Bushwalks & Local Culture

Wind pushes at your back as you walk up from Manly, the air already salted before the sun clears the horizon. The day opens on Shelly Headland, where the path crunches underfoot and the Pacific feels close enough to touch, then widens into North Head proper – war-era remnants tucked between scrub, views back to the city’s high-rises like a distant mirage. By late morning, you’re tracing the Manly To Spit Bridge Coastal Walk, the sound of cicadas rising from the bush as the track dips to quiet harbour coves and climbs again to sandstone ledges. Lunch is casual and harbourside along the route, bare arms against warm timber railings, before you push a little further into Sydney Harbour National Park, where the smell shifts to eucalyptus and dry grass and the light turns that pale, humming gold. Afternoon is for lookouts: Yiningma, Burragula, North Head lookout – each a slightly different angle on the same interplay of ocean, heads and city skyline. As the day softens, you return to Circular Quay, trading hiking boots for something with laces and leather. Evening stretches out on the water aboard a private harbour cruise, city lights flickering on glassy black, then contracts into the brick-and-sandstone intimacy of The Collective in The Rocks, where conversation rises over clinking glassware and low, warm lighting. Tomorrow, you’ll swap cliffs for pools and the softer curves of the eastern beaches.

Morning arrives as a soft roar at Coogee: waves throwing themselves against the rocks, the sharp tang of salt and sunscreen already in the air. You pad down to Giles Baths, where the pool feels like a secret amphitheatre carved into the coastline – jagged rock walls, water sloshing in rhythm, locals sliding into the sea with the casual grace of people who do this every day. From there, the Bronte to Coogee Coastal Walk unspools beneath your feet, a well-kept ribbon of path with views that keep demanding you stop and look. By late morning you’re at Bronte Baths, the concrete underfoot warmed by the sun, sea spray cooling your shins as you towel off and eat with wet hair and bare shoulders. Afternoon is for the Bondi to Bronte Coastal Walk, that much-written-about stretch of cliff where the path winds past sculpted sandstone, small coves and the kind of blue that never quite translates in photos. You end up back in the inner east, trading swimmers for something linen and light at NOUR, where the air smells of charred flatbread and spice, then sink into a quieter pocket of Surry Hills at The Blue Door. Tomorrow, you’ll turn your gaze inland for stories carved into sandstone and paint rather than rock and tide.

The day opens in Glebe with the smell of espresso and old paper – a neighbourhood where students, long-time locals and the odd professor share footpaths under plane trees. You start slow at Gleebooks, coffee in hand, fingers trailing along spines in the bookshop’s shelves before you slip into the back for whatever small event or quiet corner is unfolding. The streets outside feel lived-in: terrace houses with peeling paint, community posters stapled to poles, the faint ring of the light rail nearby. Late morning, a historical tour pulls the threads tight, giving context to the Federation facades and church spires you’ve been walking past. After a casual lunch back along Glebe Point Road, you cross the city to Lavender Bay, where Wendy Whiteley’s Secret Garden drops you into a different register entirely – shaded paths, rusted sculptures half-swallowed by foliage, the harbour framed by fig branches. As the light softens, you drift back to Circular Quay, where the sandstone blocks of The Rocks hold the day’s heat. Evening is part history lesson, part pub crawl on The Rocks Historical Pub Tour, the air inside thick with old timber and stories. Tomorrow, the wild comes back into focus as you head south to Royal National Park’s rawer coastline.

Today smells like eucalyptus and salt from the moment you step out: the air cooler, the light a little harsher, the city receding in the rear-view as you head south to Royal National Park. At Eagle Rock, the coastline feels rawer than anything in the city – cliffs dropping straight into whitewater, the wind carrying spray up to sting your cheeks. The track between Wattamolla and Eagle Rock is a patchwork of sandy sections, rock slabs and heathland, the crunch under your boots a steady metronome as you walk with the ocean always somewhere to your left. Lunch is simple and carried in your pack, eaten on a flat rock with the sun warming your spine and the roar of waves as background. In the afternoon, you take on a quieter stretch of the Royal National Park Coastal Walk, where the crowds thin and the sense of being out-there increases with each kilometre. By the time you’re back in the city, the sandstone towers of the CBD feel almost surreal. Dinner is low-key near your base, something hearty and close, before you collapse into bed with that pleasant fatigue only a full day on the trail can deliver. Tomorrow, the mountains call – different rock, different air, same pull.

Today trades salt air for something cooler and taller: the Blue Mountains, that classic three-day side-trip locals recommend condensed into one very considered day. You leave the harbour early, streets still damp from overnight sprinklers, and by the time you reach the mountains the light has changed – softer, filtered through gum trees, with that sweet, slightly smoky eucalyptus scent in the air. The Blue Mountains Nature Tour carries you between lookouts, waterfalls and wildlife stops, each one a different way of understanding how this sandstone plateau holds water and time. Lunch happens somewhere between viewpoints, maybe at a café in a small town where the chairs are mismatched and the pie crusts are flaky, or as a simple meal overlooking a valley that seems to go on forever. The afternoon folds in Scenic World-style viewpoints and quieter forest paths, the temperature dropping a few degrees as you descend into gullies. By the time you’re back in Sydney, the city lights feel almost too bright after the layered blues and greens of the ranges. Dinner is close to home, a quick, satisfying bite before a slow wander through Potts Point’s terrace-lined streets, where Spicers Potts Point offers a nightcap and that hushed, residential calm. Tomorrow, you give the city one last, salty encore along the Bondi to Coogee line with stories carried by the land’s first custodians.

Your last day loops back to the coast, but with new layers. Morning at Bondi begins not with a pose on the promenade but with Walangari’s Aboriginal Cultural Experiences, where stories of Country, songlines and rock engravings reframe the sandstone and surf you’ve been moving through all week. The sound of waves underpins the guide’s voice, and suddenly the headlands and bays feel less like scenery, more like text. Later, you walk another section of the Bondi to Coogee Walk, this time slower, noticing details you might have missed before: a particular curve of rock, a cluster of native plants clinging to a cliff face, the way the light hits a pool at midday. Lunch is unhurried along the path, the afternoon reserved for one last quiet headland – Long Reef, where the city feels distant and the coastline stretches away in both directions. Evening brings you back towards the inner city: a pre-dinner wander through Local Edition’s art-lined space in Glebe, a final, thoughtful meal at Jane in Surry Hills, and, if you have the energy, a last drink in a cosy corner somewhere that already feels familiar. You finish salt-dusted, footsore and oddly grounded – like you’ve learned the city by walking its edges.