I will have five nights in Tuscany in between Rome and Florence in June. I plan on renting a car, but I need to pick a base. I would rather stay in or very close to a small town as opposed to at a farm house in the countryside. I'll be traveling alone and would prefer the option of being able to walk in the evening to have dinner and some drinks.

I want to do some day trips to Montalcino, Montepulciano, Cortona, and Assisi. I'd also like to visit Siena if I have time, but I've already been there so its not a must see.

Any recommendations for a good town as a base or even a specific apartment/home to look into renting?

I thought about just basing in Florence because there is an apartment there that I have stayed at a couple of times that I love. I'm thinking, however, that driving in and out of Florence every day trying to avoid the ZTL, plus the parking situation would be a nightmare. Has anyone done this?

My wife and I did Italy this past summer. We did Florence, Rome, and Positano and stayed in Assisi for a night before heading to Rome. We booked the night at Hotel Pallotta Assisi and loved it. Small enough town where 1 night was enough, although short stay, it was gorgeous and worth it.

Montepulciano and the surrounding region is amazing. In all honesty all of Tuscany is just wonderful. Wine, food, scenery and the people are all great.

San Gimignano was great. Stayed at Hotel Cistern, very nice.

We stayed in Trevi last summer and visited lots of places from there. Saw Assissi, had wine in Spello, made chocolate in Perugia and a couple other places. It was a great home base!