There are some really nice walks in the heart of Simon's Town. Here are a couple:
1) The Waterfall
Start at the Shell Petrol Station in town. Walk up the steps to the left of the garage. Follow the steep roads up the hill looking for the "skilift" pylons which will lead you to Barnard Street. The path to the waterfall begins where the road ends and it is a flattish easy path. It should take no more than 20 minutes to get from the start to the waterfall.
1) Just Nuisance Grave
The grave of our famous dog is at the top of the hill above Simon's Town and while it is a tough climb up the steps to the top, the view is well worth it. The mountain steps begin on Barnard Street and lead up to the Navy Signals area where the grave is located.
Pictures and video of the walk