A Week in Tuscany with car (reply)
Buongiorno KJBurkhardt,
welcome to Discover Tuscany forum!
The period of the year you've planned to come to Italy is perfect: not so crowded and not so hot yet! The idea of renting a car to come to Tuscany is a great one.
But before leaving the wonderful region of Emilia Romagna,
don't miss Bologna and Ravenna. The latter is close to Cervia and its history is strictly connected with the Romans and the Byzantine Empire. There are many churches and remains dating back to Roman age. Furthermore the great Florentine poet Dante Alighieri, the father of Italian language, is buried there.
You will ask: why not in Florence? Well, because he was exiled during one of the countless civil wars old Florence faced regularly before it became the "cradle" of the Renaissance.
As to Bologna, since you're planning to rent a car there...that city is worth a visit before heading to Tuscany. It's a charming place which has preserved its medieval mood through the centuries. Its urban plan gives you an idea of how a typical Italian city looked during the Middle Ages (aside from the cars!!

) Don't miss the tower houses known as "Garisenda and "Torre degli Asinelli", veritable skyscrapers of that time.
As regards Tuscany, you wrote you already visited Florence last year and you're planning to visit new cities. Well, you'll be spoiled for choice!
Siena is a wonderful historical city, not as crowded and polluted as Florence and no less interesting than the Tuscan capital. Moreover its surrounding area and its countryside are beautiful and day trips are feasible.
There are many things to see.
On the first day you can visit the old city and its major attractions such as
the Cathedral (a must see!), the many "palazzos" of the city center or the famous "Piazza del Campo" where the annual "palio" (horse-race) takes place.
If you have a car, it'll not be a problem to reach the nearby towns. I can recommend, for example,
San Gimignano. It is worth a visit: a delicious small city famous for its tower-houses and its relaxed atmosphere.
On another day,
you could visit the Chianti area (north of Siena), famous for its hills, vineyards and red wine. This is just a short list of some of the most interesting small towns you may want to see:
Castellina in Chianti, Gaiole in Chianti or Radda in Chianti, the three in the north-eastern part of the Province of Siena,
or Greve in Chianti (just on the border between Florentine and Sienese provinces). All these towns are the ideal place where you can refresh yourselves and taste a good glass of red wine with some local specialities.
And if you want to get rid of the crowds and discover a very special place...I recommend you go to
the Abbey of San Galgano located to the west of Siena. A unique place: a huge abandoned abbey in the middle of the countryside that will move you with its echoes of ancient knights and monks.
I think these are the main attractions you can visit if you choose Siena as your base and if you have a car.
I am sure you will love that part of Tuscany and I also hope you'll find my suggestions useful
Kindest regards
Fabrizio