Florence-Siena-HillTowns in 5 days

Florence needs two full days min. Siena is a day trip from Florence. For the two addional days a car would be helpful to get the most of your time visiting small villages and countryside. There are a few thousands villages, towns and cities in ztuscany. Choose what fits your desires:
www.borghiditoscana.net

If you stay in Florence, you can easily day trip by bus to San Gimignano and Siena in the same day. You are not there long but Grayline (CAF Tours in Florence) has a tour that does it. You can also use public buses to get to and from Voltera. If you base out of Siena, you can day trip to Florence. It's an hour each way by bus or train. But, if you stay with public transportation, it will be difficult to see a lot each day. True, there is bus transportation out of Siena to many Tuscan hilltowns but the service is not frequent and the wait times as you change buses extends the travel time. Also, if any of your travel is on a Sunday, bus transportation in Tuscany if severly reduced.

Ruth, if you have a car I recommend you stay out of Florence and visit there on a one day basis,twice if necessary. Remember to prebook your tickets especially for the Uffizzi and or the Academia. We did this while staying in San Gimignano at the Leon Bianca, an excellent hotel. San G. is great base for touring around the other hill top towns. Caution do not drive into Florence, take the bus,it's simple and almost direct. Caution two, do not drive into Siena on market day, other than then, no problem,Bill.

Ruth, each opinion you get will reflect the author's interests/experience. For example, I'd happily spend all 5 days in Florence, while others would skip it altogether. The best solution would be to decide what interests you. I'd suggest getting a guidebook or two and identifying the "must sees" in towns you know you will visit (sounds like that's Florence, Siena), along with an estimate of time you'd like to spend at each site. That will tell you how much time you have left for other towns. The Rick Steves guides tend to be selective; they only identify the towns he targets, but they do a really good job of telling you what's in those towns and how much time you might want to allow for a quick visit. The DK Eyewitness guides are short on details, but have lots of photos and describe a wider range of towns than the RS guides.

We love the museums and sites but we also enjoy just getting a feel for the local fare. We have a vineyard so we love wine and all that goes with that as well. We just want to get our reservations so we can then plan our days so any help on that part is great.