We will arrive from Venice and have four nights before leaving for CT. We will not have a car. We would like to see Accademia, Duomo, like some art and cathedrals but not sure what else. We prefer smaller towns, maybe hill towns?... What towns should we stay in, and what would you do with those five days?
We could rent a car, but just thought for the amount of time it may not be worth it. Could tell me what you would suggest if you were doing the trip?
no need to rent a car while in Tuscany, especially if you only have a few days. you can easily fill your time with one or 2 days in Venice, then take the train to FLorence (2 and a half hours, but you probably need to make a reservation at least a day in advance )and spend a full day or more in Florence. If you want to visit the Uffizi, it would be a good idea to get tickets online to avoid the lineup. If you want to take a day trip from Florence to Siena, you can easily take a bus. While in Venice you could take a day trip to Verona.
Verona is nice, Florence has great art - neither is the hill town experience you are looking for. Driving from CT toward Rome with Florence in the middle we visited: Pisa (for the basic photo op), Lucca (only okay not a classic hill town, the wall looks late 18th/19th century), San Gimignano (great medieval town even with the tourists), Siena (beautiful city but not a small town), Orvieto (really liked this Umbrian large hill town). Of the group, the only one that really captured the "hill town" imagination was San Gimignano. Next time I'll look harder for smaller, medieval towns like it.
Definitely get reservations for the Uffizi and Academia so you can visit the must sees in a timely manner.
So, in addition to the obvious -- Florence -- you might consider a night or two in Cortona, as you can get there reasonably easily on the train from Florence. Get off at Terontola and either take the shuttle bus (every hour) or a taxi. It's about 10km from the station to the town.
Cortona is definitely the hill-town experience: lots of steep streets, romanesque churches, people watching at Passagiata, a good museum and some nice restaurants. Great for a day or two -- any longer and you will be bored. Last time we stayed at a hotel called Villa Marsili. Really nice place with super-helpful staff, incredibly great breakfast (I normally don't rave about that kind of thing... but it was fab) and a nice garden for drinks outside in the evening.
Finally, you can (and probably should) rent a car for the best Tuscan hill town experience. And next time, consider staying longer -- see http://lodgephoto.com/blog/?p=13
Mathew