Think Sydney Harbour is just the Opera House and Harbour Bridge? Think again! While those iconic landmarks are undeniably breathtaking, the harbour stretches far beyond — revealing a world of lush greenery, elegant waterfront mansions, native bushland, and secluded sandy beaches. With a sprawling 317 km perimeter, it’s not only Australia’s deepest harbour but also the birthplace of modern Australia. There’s so much to explore, you could easily turn it into a two-week walking adventure!
But why not start with something more bite-sized and spectacular?
Introducing a unique way to experience Sydney: a 3-day, 2-night walking holiday that unveils the harbour’s best-kept secrets. You’ll stay at the stylish Rydges Australia Square Hotel, right in the heart of the city, and set out each day to explore hidden corners of the harbour that even lifelong locals haven’t discovered.
With scenic ferry rides connecting each leg of the journey, you’ll walk through some of the most stunning and surprising stretches of the harbour. From quiet coves to panoramic lookouts, this getaway promises beauty, serenity, and a few delightful surprises along the way.
Ready to see Sydney from a whole new angle?
🎒 What’s Included in Your Sydney Harbour Walking Escape
This 3-day, 2-night adventure is packed with everything you need for a memorable getaway:
🥾 Three guided hikes through stunning and lesser-known parts of Sydney Harbour
🛏️ Two nights’ accommodation at Rydges Australia Square Hotel, right in the heart of the city
🍳 Two delicious buffet breakfasts to fuel your mornings
🍻 Two hearty pub lunches (yes, they’re genuinely excellent!)
🎁 A fun goodie bag to kick off your journey
🌉 Entry to the Harbour Bridge Pylon Lookout, offering panoramic views of the city and harbour
With a maximum group size of just 12, this experience is intimate, relaxed, and personal. You’ll explore by day, and enjoy your own free time in the late afternoons and evenings. Whether you’re keen to catch a show, indulge in fine dining, or simply unwind with a movie in your hotel room.
The cost for the 3 days mini walking holiday is $775 per person twin share or $1150 per person for solo occupancy (room by yourself). Please note: for twin share, you must book with someone you know, as we’re unable to pair individuals.
🚶♂️ About the Walks
All walks are graded easy, ranging from 8 to 12 km. While there are a few short hills and staircases, the pace is steady and relaxed — designed so everyone can soak in the scenery. You’ll traverse a variety of paths including boardwalks, bush tracks, beaches, concrete paths, and quiet street sections. Expect to walk for about 3 hours the first day, and 5 hours the second and third days. This isn’t a speed challenge. If you don’t like stopping and looking at things, this might not be for you! There is a lot to look at on these walks!
This is not just a walk — it’s a chance to connect with nature, discover hidden gems, and experience Sydney from a whole new perspective.
The first walk on the Friday starts at 1.00 PM and the last walk on the Sunday finishes at 3.00 PM at the latest. It is a 29 minute train journey from the city to the airport – so please book return flights (domestic) well after 6.00 PM. We can arrange an extra night’s accommodation if you need this.
Upcoming dates:
November 13-15, 2026 – sold out but please see below…
We can run the program for groups on any dates, with a minimum of 6 people (subject to availability). This is a popular weekend for private groups of friends, families or for corporate events. Please contact us to organise your own private group walking getaway!
If you live in Sydney or have friends you can stay with in Sydney, you can still come along! Without the accommodation and breakfasts included, the price for the 3 days of walking is $390 – this includes the 3 guided walks, 2 really good pub lunches, entry to the Sydney Harbour Bridge Pylon Lookout and Museum and a goody bag.
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