Sydneysiders have turned walking into an art form — whether it’s along coastal cliffs, through leafy laneways, up to harbour lookouts, or down historic staircases in The Rocks, it’s all about the journey. As a renowned walkable city with many landmarks close together, Sydney offers an array of walking tours that delve into interests from history, crime, nature and food.
Do be mindful of the urban sprawl — Sydney is extensive and while the core is walkable, outer suburbs require wheels. Exploring Sydney on foot with a knowledgeable guide uncovers fresh perspectives on iconic sights and reveals hidden corners you might otherwise miss — inner-city alleys with a shadowy past, one of Sydney’s oldest bakeries, and legendary tales of trailblazing immigrants. So why not come on an inspired wander through the harbour city?
1 Sydney by Night: Secret Bars and Stories
Award-winning touring company, Local Sauce, offers a bar crawl around some of Sydney’s coolest drinking holes. Meet your host (the venue changes depending on the night) and leg it to three to four different local bars. Enjoy a drink – first one’s on the house – while listening to boisterous tales about local legends. There are five different routes taking in Sydney’s eclectic small bar scene: Tuesdays it’s the city’s York, Clarence and Kent (YCK) street precinct, while on Saturdays you’ll criss-cross Surry Hills and Darlinghurst.
2 She Shapes History: The Women Behind the City Tour
Walk in the footsteps of trailblazing women – activists, writers, pub owners, nurses — who shaped Sydney. ‘She Shapes History’ operates walking tours nationally, and the Sydney itinerary begins in Hyde Park, where Gadigal women once gathered. You’ll stroll Macquarie Street where one woman saved some of Sydney’s most iconic buildings from demolition in the 1940s, visit the original Government House, and finish up in The Rocks, listening to stories that few Australians ever hear.
sheshapeshistory.com/sydney/badass-women-of-sydney
3 Fit City Tours: Harbour Sights Running Tour
Why walk when you can run? Fit City Tours operates guided running tours through the city, from the Opera House and Sydney Harbour Bridge to the narrow alleyways of The Rocks. It’s a fun combination of fitness and sightseeing, with a local guide to share their insights. The Harbour Sights Running Tour starts at 7am in Hyde Park and winds for nine kilometres through the Royal Botanic Garden, across the bridge and into the secluded Wendy Whiteley’s Garden. Finish with a coffee then catch the ferry back to Circular Quay.
fitcity.tours/destinations/sydney
4 The Fabulous Wonder Mama: Walking Tour of Oxford Street
Oxford Street Darlinghurst is the epicentre of Sydney’s colourful LGBT community. Join Wonder Mama – Australia’s favourite super hero drag queen – on a walking tour that takes you past iconic gay venues like Stonewall, The Oxford Hotel and Darlinghurst Bookshop. She’ll share fascinating stories about the history of the area, the local LGBT movement and the famed Sydney Mardi Gras. The two-hour tour will introduce you to a side of the city you’ve never seen.
fabulouswondermama.com.au/walking-tour
5 Secret Food Tour: Sydney
This three-hour culinary journey of Surry Hills uncovers gastronomic delights and exclusive eateries in Sydney. At lesser-known foodie spots adored by locals, try honey biscuits from Sydney’s oldest Greek bakery or freshly shucked oysters. In between flavour stops, you’ll be guided past a mix of old-world glamour with grand churches, leafy lanes and trendy boutiques. All this and fascinating stories about Sydney’s post-war immigration and the Greek, Italian and Portuguese culinary influences that shaped the way Sydneysiders eat.
6 Three-Day Royal National Park Walk Coast Track
From the milky-white cliff faces to secret beaches and pockets of rainforest, this three-day coastal hike in Sydney’s south spanning 26 kilometres, is ideal for nature lovers. With an expert guide from Life’s An Adventure, you’ll enjoy a mix of bushwalks and coastal views on the Royal National Park coastal trail from Wattamolla to Otford, then to Bundeena over two nights and three days. It’s a pack-free walk with lodgings and gourmet meals part of the adventure.
lifesanadventure.com.au/tours/royal-national-park-walk
7 The Rocks Walking Tours
Rich in colonial history and lined with cobbled lanes, The Rocks is Sydney’s oldest neighbourhood and the site of the first European settlement in 1788. Once home to convicts and dockworkers, it’s famed for its gritty past. The best way to uncover its curious beginnings is on The Rocks Walking Tours — expert guides lead you along the harbour shoreline, down dimly lit lanes and past heritage facades, sharing tales of the area’s original inhabitants.
rockswalkingtours.com.au/walking-tour
8 Australia in Style, Sydney Sightseeing Tour (Wheelchair Accessible)
If you have mobility or sensory challenges, these inclusive tours ensure that everyone can enjoy Sydney’s iconic hotspots. They offer customised experiences, with seamless access to Sydney icons and natural wonders for those with walkers, wheelchairs, or various disability levels. The Australia in Style team have more than 15 years offering step-free tours, and they’re proud to have been awarded the NSW Tourism Award for Excellence in Accessible Tourism.
9 Surry Hills Crime Scene Walking Tour
Calling all crime buffs and armchair sleuths, this one-of-a-kind walking tour lures you down dark Sydney lanes to crime scene locations from the 1820s to the 1960s. Hear gruesome tales of murders that took place in historic terrace houses or on Surry Hills street corners. Stand in the spots where bodies were actually discovered and learn about the police investigations. All this plus a final stop at a historic pub for a drink and a debrief.
10 Sydney Sights Free Walking Tour
Sydney could take a lifetime to explore, but this walking tour manages to capture most of the highlights and tell you Sydney’s story in about three hours. Local guides shepherd you to Sydney Opera House, the infamous ‘Rum’ Hospital, Cadman’s Cottage, and Queen Victoria Building among others, stopping at regular intervals to explain significant facts. The best thing? It’s free. The tour works on a ‘pay what it’s worth’ concept, so people on any budget can enjoy this fabulous city. Runs 10.30am daily from Town Hall Square.
