My husband and i are planning a trip to tuscany in October. we plan to stay in Florence for 3 nights and the rent a car and drive to our hotel in Radda. Can anyone suggest the best route to take to Radda where we can see some interesting towns on the way to our hotel? also is it possible to see Montepulciano, Montalcino, and Pienza on a day trip from Radda? Any suggestions for day trips out of Radda?

forgot to also say we're staying in Radda for 5 nights. Driving back to Florence last day to fly home.

You picked Radda as your base but are asking about 3 wonderful hill towns all at least 1.5 hours south of there. Yes, they are doable from there but not easily. Why did you not base at least as far south as Siena?

Bob brings up a valid point. You might be better served by doing one of two things. If you are set on the hill towns you mentioned, base yourself a bit closer to the southern part of Tuscany. Or if you are set on a Radda base then concentrate on the areas closer to Radda. There are lots of things there to do. You could easily day trip to Siena. Greve in Chianti is interesting. Certaldo Alto, San Gimignano and Volterra are also within reach.

Thanks for the info. I am looking at possibly staying in Castelnuovo Berardenga which is further south. Also, we will be renting a car. is it necessary to have an international driver's license?

You will need an international driving permit if you happen to have any encounters with the Italaian authorities while driving your rental car. You won't actually need it to rent the car. It costs about $15 at a AAA store and you should get it before you leave. You'll need 2 passport size photos and your drivers license from here. Most AAA stores can also take your photo too.

You'll see lots of posts from folks that did not get them and were never asked. Ignore those posts and just get one. Supposedly the fine for not having it if you are stopped or get bumped by someone and need to call the cops is 50 to 75 euros. there have been some reports of people getting their car impounded.

Do not pick the hotel first---a common mistake. Pick the location---there are plenty of great places to stay.

any suggestions for hotels in the castelnuoevo b. area?

The advice you have already received should be reviewed with reference to a detailed map of Tuscany. Castelnuovo Berardenga is even more remote than Radda from the southern tuscan towns you are interested in visiting. What is your goal? If Chianti, fine to stay in Radda or Castelnuovo Berardenga. But if it is daytrips to Montalcino, Pienza or Montepulciano, then locating in Siena or south is far better. I would even argue that Chianti, especially where you are considering, is not convenient for San Gimignano or Volterra--too long a drive over windy, hilly, tight roads.
good luck--Paul

Paul, Castelnuovo Berardenga is just east of Siena. So they have moved about 30 minutes closer.

Look at a nice B&B named Borgo Argenina. But, how did you pick that area? What is your rationale?

OK I have my map. And thank you,notbob, I KNEW I wasn't crazy! C.B. is actually closer to Montalcino and the other towns I'd really like to see. What's my rationale? I'm trying to get closer to the Montalcino area but still be within day trip distance to some of the Chianti towns as well. I was thinking of visiting Greve and possibly Panzano on our drive from Florence to C.B. and then take day trips to Siena, Castellina, Radda and Gaiole and maybe some others.I would really like to visit Orviato in Umbria too, but I know I can't fit that in. In other words, I want to do it all. What I really need is more time!! (More money would help too!)

OK--I understand you want to see it all from one destination. You are right, you need 6 nites and 2 destinations to do it well. Why not just stay on the edge of Siena and drive from there. Look at the Santa Caterina hotel at the Porta Romana gate into Siena, or the Palazzo Ravizza in Siena with parking.

Why not stay 2 nights in Radda and 3 nights in Montepulciano or Montalcino Or vice versa?

Or stay very close to Siena as Bob suggested. Staying in a very small village for 5 nights may not give you as lot of dining options. I don't drive after drinking wine at dinner and our non-drinker won't drive on winding Tuscan roads after dark. Which isn't quite right, because she won't drive on them in the daytime either,

Thanks for all the info. we're probably going to stay right outside Siena. When I first made the decision to stay in Radda, I had not heard or read about Montalcino and the others until I read this forum that described them. The more I read the more I knew I had to go there!

Good for you---have fun !

As i was reading the other postings in the forum, I came up with more questions. I keep reading that shops and restaurants are closed on Sundays and Monday mornings. is this everywhere? just some towns? any suggestions what our itenerary should be on those days? We'll be leaving Florence early on Sat. Oct. 11 and driving to Siena, probably sightseeing on the way. Not sure which towns to see that day. Then we'll be in Siena Oct. 11 through 16. The day after we arrive is Sun. Oct. 12.