Lucca is a wonderful walled city one hour train ride west of Florence, towards Pisa.
It is not a hill town, but it has a wonderfully preserved town wall which you can walk or cycle around in 40 minutes, looking down into the Renaissance town. The wall is very accessible and is 4.6 km in length.
There are many ramps down into the town from the wall at various points along.
There are 4 or 5 main gates and a few tunnel-like entrances between them.
Few of these are wheelie accessible so use the main gates unless you are intrepid.
the one opposite the train station has a ramp with steps. Another further around towards the Eliza gate has a very steep heavily cobbled ramp. I struggled down it but risked breaking my suspension. Another past the Eliza gate has a closed rusty portico.
Lucca has three or four main thoroughfares (at least the tourists seem to love them, lined with expensive shops or touristy souvenir shops. There is a charmless amphitheatre which also seems inexplicably popular.
As usual we wandered off these crowded spots and found lovely winding backstreets and charming little restaurants.
There is a very long market in Via dei Bacchettoni some days. Wednesday morning comes to mind.
Check here: tuscany.angloinfo.com/whatson.
My favourites are the comic (fumetto) museum, Museo Nazionale di Palazzo Mansi.