Guided walks for over 55s

Come and explore Sydney and the great outdoors with us, meet new people, bring a friend! You don’t have to be a member of Vintage Fitness to attend.

• The next route: City Explorer
• Date: Monday, 17 August 2026*
• Start time: 11:30am
• Cost: $20  

*Can’t make this date? Scroll down for the 2026 calendar.

What will you see on this beautiful walk?

This is the kind of walk that reminds you why we live in such an incredible city. Expect a relaxed pace, fresh air, and a chance to soak up some of the oldest (and newest) parts of Sydney.

Along the way we’ll visit:

• The Rocks
• Dawes Point
• The Tea Cosy
• Walsh Bay
• Barangaroo Reserve
• Observatory Hill
• Fortune of War (Sydney’s oldest pub)

Plus plenty of hidden gems and historic streets along the way. It’s the perfect mix of gentle exercise, great company and site seeing.

Additional details for your walk

• Start & Finish: Customs House 
• Difficulty: Moderate – relatively flat along paved roads. 
• Timing: Allow around 2.5 – 3 hours
• Distance: 6-7kms 
• Bring: Water (we’ll have extra), sunscreen, a hat, and a light backpack for your bits and pieces.   

Getting there – transport information

One of the easiest ways to get to this walk is by public transport. 
Check NSW Trip Planner for the best route for you. 

Book now – this is a great walk – you don’t want to miss this one!

Urban Walk Calendar – 2026

Pop these dates in your diary and look forward to your monthly fix of fresh air, great views, and good company:

• Monday 11 May – Manly to Curl Curl
• Tuesday 16 June – Rose Bay to Watsons Bay
• Monday 17 August – City Explorers Walk
• Tuesday 15 September – Route TBC
• Tuesday 13 October – Route TBC
• Monday 9 November – Route TBC
• December – Date & Route TBC

We’ll share full details and booking links closer to each walk.