Montepulciano is so nice! We stayed here, which is right outside -- https://www.follonico.com/en/index.html

Even just picking up my car in Florence I accidentally drove through a ZTL and got a traffic ticket in the mail a year later

Anonymous wrote:OP and thank you for all of the ideas. I've expanded my research to consider some of the smaller cities and towns. We don't mind driving in Italy, my car concern is really about parking options staying somewhere like Florence.

I'll report back after our trip to help anyone who does a search later this year.

Yeah you don’t park in Florence. You pick it up as you leave town or drop it off as you arrive.

OP and thank you for all of the ideas. I've expanded my research to consider some of the smaller cities and towns. We don't mind driving in Italy, my car concern is really about parking options staying somewhere like Florence.

I'll report back after our trip to help anyone who does a search later this year.

Anonymous wrote:We stayed just outside Cortona and got to daytrip around Tuscany and Umbria.

I love Cortona. My favorite Annunciation painting is there.

If you get a car, I'd suggest renting a villa 2 or 3 miles outside a small town in Tuscany. You'll get more space, easy parking and maybe a pool, and can plan day trips, avoiding traffic jams getting home.

Pick up supplies at markets and enjoy the view.

I would do Siena, or someplace nearby in the Val d’Orcia

We stayed just outside Cortona and got to daytrip around Tuscany and Umbria.

We stayed at Il Boro near Arezzo! Perfect base and beautiful facility. Took train to Florence but drive to Sienna, montepulciano, Cortona etc… would do it again in a heartbeat.

We visited Florence for three days in 2019 as independent travelers (family of 4).

We spent 2 days in Florence and the 3rd day we took this exact bus tour with the company below. The company has many other tours.

https://www.ciaoflorence.it/en/tour-detail/13

From going on the bus tour, they told us that if we got lost from the bus tour, the tour company home office could help us get back to Florence from Siena by train. So my guess is, it's pretty easy to go to and from Siena on your own. The bus tour left from the back of the main Florence train station.

We stayed at the Hotel Torre Guelfa. It's quirky and not deluxe but cool anyway. It has an antique breakfast room and a rooftop view that hotel guests can make use of. Rick Steves recommended it. In good weather you can walk to it from the train station. It's close to the historic center of Florence, near everything.

https://www.hoteltorreguelfa.com/

I felt a lot of the AirBnB's I saw listed for Florence were sketchy. My husband and I don't like to drive overseas unless it's impossible to get around. The one day bus tour of 3 cities saved us a lot of cost and hassle. You might feel the same.

Enjoy trip planning.

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:You should rent a car, that will be easiest way to see the region by far.

But not if they want to actually stay in Florence or Siena.

Italian cities are tough to drive in (many city centers don't even allow car traffic anymore) and parking is a nightmare.

The hilltop towns are difficult to visit without a car. You can park in the outskirts and walk to the center.

Yeah, visit Florence for a few days and then pickup a car on the way out of town. You could even do a one way rental to Siena or Rome or whatever.

Anonymous wrote:

Anonymous wrote:You should rent a car, that will be easiest way to see the region by far.

But not if they want to actually stay in Florence or Siena.

Italian cities are tough to drive in (many city centers don't even allow car traffic anymore) and parking is a nightmare.

The hilltop towns are difficult to visit without a car. You can park in the outskirts and walk to the center.

Anonymous wrote:You should rent a car, that will be easiest way to see the region by far.

But not if they want to actually stay in Florence or Siena.

Italian cities are tough to drive in (many city centers don't even allow car traffic anymore) and parking is a nightmare.

You should rent a car, that will be easiest way to see the region by far.

We are considering renting an AirBnB somewhere in either Florence or Sienna and using it as the base for 4-5 days of day trips around Tuscany. We would rent a car if needed, but leaning towards using trains.

Has anyone done this and if so do you recommend one city over the other? Added bonus, recommend your favorite neighborhood to stay in.