Cinque Terre, Tuscany or Umbria
 

We will be making our way from Venice to Rome in mid October. I'm travelling with elderly mother, so hikes are out. Easy, short walks about 1km on flat ground or very short gentle slope is doable. We will have a wheelchair for me to push wherever possible to conserve her energy. I want to expose her to beautiful countryside and architecture, Italian culture and hopefully engage with locals. I travelled through parts of Italy many years ago, including Pisa and Florence. So, we are not interested in going to these cities and hoping to enjoy stays in smaller/quaint villages with lots of character/charm.

I liked the idea of Cinque Terre as it is unique compared to Australian coastline, but a little worried about how much effort it will require if we stay in Monterosso and catch a ferry to admire the villages???

Next, we are (at this stage) off to Lucca, as it was suggested as a lovely destination and easily accessible. From here I'm planning on renting a car, and going for short drive through Tuscany (eg Montepulciano and Monticchiello) perhaps Umbria (Spello and Orvieto) and sample some lovely Italian wine. However, I'm unsure where we should go and hoping someone could shed some light on the most scenic and enjoyable route, including a few stops to vineyards/wineries?

I'd cross CInque Terre off the list right away. At that time of year you risk closures due to inclement weather, and I think a wheelchair would be a huge pain. Have you thought about how your mother will get around Venice also?

How many days do you have for the "short drive" part of the trip?

I think all three areas could be problematic. I can't evaluate your mother's mobility based on your comments, but my elderly mother who doesn't need a wheelchair would have trouble walking in all of the towns you mention with the exception of Lucca and perhaps Orvieto. And I wouldn't be able to push her in a wheelchair in any of them with the exception of Lucca and perhaps Orvieto. Orvieto is the only smallish towns I can think of that has bus service in the historical center, but I don't know if the buses can carry wheelchairs. Assisi has bus service from the parking area that circles but doesn't travel through the historical center. Again, not sure about the wheelchair on the bus.

In Tuscany you could consider Pienza, San Quirico, Volterra and Greve which are more or less flat with parking not far outside the center. In Umbria, I suggest Bevagna and perhaps Todi. Orvieto has a funicular connecting the parking area to the center plus the mentioned bus service. Todi also has a funicular from the parking area and a flat piazza in the historical center, but I can't remember what the walk from the funicular to the piazza is like.

Orvieto is flat once you get up the hill to it. The duomo is absolutely gorgeous. Lucca also not hilly. Montepulciano and Montalcino do-able, again, once you get up the hill to them.

Another vote for San Quirico d'Orcia. Check out Hotel Palazzo del Capitano.

Another idea in Tuscany... Montecatini Terme. The newer town is flat with some nice architecture, fountains, a big park. There is a funicular to the tiny historical town on the hill. The view from the top is great, but getting from the funicular to the main piazza involves a somewhat steep walk for a short distance. There is bus service from Montecatini Terme to Montecatini Alto.