Tuscany. Easy access

The Chianti villages between Siena and Florence are not terribly hilly, Panzano has a hill in the oldest part, Castellina, Radda is flat. Siena has transport up or park at the top of the hill. You mention “ hill top” so Cortona comes to mind, Siena.

I'm not sure how many of these would be considered "hilltop" towns, but we drove through Tuscany for a week, based in an agriturismo outside Montepulciano and were able to access that town, Siena, Bagno Vignali, Pienza, San Querico, also Pisa and Lucca, Montalcino, Cortona and then on to Assisi and Orvieto, for 2 nights each of the latter places and returned the car in Orvieto. Parking was available, but it helped to research where the lots were before entering the towns themselves. For example, somewhere like Assisi did not allow driving unless you were staying in the town. We are also seniors who like convenient access, but we found all of these areas fairly do-able.

Have you decided where you will overnight during these 7 days?
Pienza would be my recommendation
Small, quiet and flat, central to lots of other towns

Pienza, San Quirico, Bagno Vignoni, Buonconvento are all easy to access and mostly flat

Montepulcuano has easy parking but the town is steep, lots of stairs and climbing steep streets

Montalcino has easy parking then a bit uphill to town which is mostly flat

Some good advice in your previous post
https://community.ricksteves.com/travel-forum/italy/tuscany-adventure

We will stay in two different area 2/3 nights in each and do day trips to other towns
Pienza looks lovely. Would we need to get a hotel outside of the town? If so, how would the walk be with Luggage getting to Hotel? Or would we be better staying outside of the town. Planning this trip to suit our abilities and I seem to be going round in circles. But so appreciate any help

We stayed here this past May and loved it
The view from our balcony was magnificent
Parking on site, steps to town- literally across the street
No elevator in this hotel but stairs were few and easy, the staff carried our bags up
Very affordable as well

https://www.piccolohotellavalle.net/en/

There are a few others just outside the walls at other end of town that also have parking on site
Hotel San Gregorio and Hotel Corsignano

For a second location I’d probably pick Lucca
Flat and to the NW so you cover both that area and the Val d Orcia area

Lucca hotel that has easy parking
10-15 min walk to center
Hotel Rex next to train station, you might even consider dropping car in Lucca and taking train back into Florence
http://www.hotelrexlucca.com/

Great ideas. Thank you so much

https://www.wanderingitaly.com/maps/valdorcia.html

Val d'Orcia hotel I would highly recommend the Locanda San Francesco in Montepulciano; for a farmhouse La Fonte near Pienza.

If Lucca is on your radar, the San Luca Palace has a parking lot steps from the hotel for €15/night without driving in the ZTL if you book direct. Ask for directions before you arrive. The suggested hotel of Locanda San Francesco in Montepulciano is not exactly easy access; it is in the highest part of town.

Parking in Pienza is very limited and it can be almost impossible to find a spot during the busy time of day. We stayed a week in Pienza earlier this year and did day trips from there. Someone above mentioned Hotel San Gregorio...we had booked a full week at a small no-frills hotel at the edge of town (based on good reviews) and were ready to leave after only a couple of days. We won't mention the hotel name or the issues, but after 5 days we couldn't stay there any longer, and moved over to Hotel San Gregorio. Hotel San Gregorio is beautiful and about the same price as the no-frills hotel, and it has a convenient parking garage underneath the hotel.

Here is a lit of interesting Tuscany towns and villages that are fairly flat, but not necessarily hilltop towns, with parking just outside the town gates or walls. Many are Italian Touring Club "Orange Flag" towns.
http://www.travelingintuscany.com/album/album10orangeflag.htm

San Gimignano
Volterra (if you park in the garage below Piazza Martiri della Libertà)
Pienza
Castiglione d'Orcia
San Quirico d'Orcia
Siena
Orvieto (just over the Tuscany border in Umbria, park in the garage and take the elevator or escalator up into town)
Pitigliano
Sorano
Sovana
Monteriggioni
Panzano In Chianti
Vertine
Montalcino (use the parking lot next to the castle)
Monticchiello
Castellina in Chianti
Castello di Fonterutoli
Castello di Volpaia
San Gusmé
Barberino Val d’Elsa
Murlo
Montefollonico
Bagno Vignoni
Buonconvento

Here's my report on Tuscany and Umbria from last March. It starts in Florence, so scroll down to when I rent a car for 9 days.
Some other posters added their experiences as well.

Which ever towns and village you decide to visit, it would be a good idea not to go directly to the town centre due to limited parking.
Siena has a one way system and if you do not have GPS you could end up going around in circles trying to get out.

I would be happier to park outside of towns, but my concern being…having parked the car, how far would the walk be into town, owing to our walking abilities. We can walk providing it is not too hilly. Would love suggestions of towns that are fairly easy to get to after parking
Thank you for your help

I would not go to Siena. We loved it but the streets can be very steep and hilly. It is not easy to get around if mobility is at all an issue. We went to Orvieto last weekend and it was not as difficult. Not part of Tuscany but not far. Great wine too.