10-day Road-trip, Round-trip from Florence

San Gimignano and Volterra are two pretty towns were you can park close and the walking is fairly flat (if I remember correctly). They are charming and good for a stroll and a meal and doing the la dolce vita thing. When we are in Italy, we just like to sit and watch, and soak up being there

I am laughing with / at your concern about your parents walking but my parent is 91 and I'm the 67 year old. Unless your parents have a disability you don't mention, have them do what I'm doing and start walking daily to build up stamina. My dad at 85 and I at 62 did fine in Italy...we built in a break for lunch at a at down Cafe everyday. We did a day trip from Florence with Walk Florence that took us to sienna,San gigniamo lunch at a winery and then Pisa. Great tour . Try and get first entry tickets if you are going to The Vatican in Rome and any other museums. That minimizes the crowds and sets up your day .We love hop on hop off buses....stay on for whole circuit. We also travel by train which is less stressful for us. You may want to consider training to and from Rome and just getting the car for days after you see Rome.

Are you planning on spending any time in Florence or Rome? Knowing this will help us steer you in the right direction as far as what stops might be reasonable.

Since you have not driven in Italy, check out ZTLS. Driving into cities and villages
Can be very costly as far as fines are concerned.

Download this informative rules of the road for Italy.
https://italybeyondtheobvious.com/

Thanks! I edited the post with a tentative schedule.

I would pick up car as you leave Sorrento, eliminates all those trains and you’ll probably have better options renting in Sorrento.

Where is your agriturismo in Tuscany?
Florence airport is only a short 15-20 min taxi from the historic center, no need to stay in a airport hotel

If your agriturismo is close enough, stay there for last night and return car in the am
I’d try to add more time to that Tuscany stay- as it is you won’t get there til late in day which gives you only 1 full day to explore the region.

Are your flights set?
Can you fly IN to Naples, out of Florence?
Fly to Naples
Sorrento 3
Get car
Coreno Ausinio 1
Tuscany 3
Drop car in Florence
Florence 3
Fly home

For your Tuscany sightseeing - Pienza is mostly flat, small and easy to walk around, and wasn’t too busy even with the ridiculous crowds in other places this spring. We visited midweek however, and it seems like your time in Tuscany covers a weekend, but October should be less of a peak time.

If you’re into wine there are plenty of great wineries in Tuscany. Good way to get off your feet and relax without the crowds (only 1 winery was truly busy of those we visited).