We (four adults) leave in two weeks for 18 days in Italy and during that time we will have four nights in Tuscany with a rental car. We will pick up the car as we leave Florence, then drop it back off in Pisa. We spend four nights at the Fonte de' Medici in the tiny town of Montefiridolfi (S. of Florence, W. of Greve). With this as our headquarters, we plan to take driving tours of the Tuscany area. Not necessarily in this order, but:

Day 1 - Chianti Road, seeing Greve, Radda, Gaiole and Castello di Brolio

Day 2 - West to San Gimignano, Volterra and Monteriggioni

Day 3 - South and East to Montalcino, Pienza, Montepulciano, Arezzo and possibly Chiusi

Are these days doable? We are aware of the the mileage, but not having driven in Tuscany before, we are finding it difficult to judge the driving times. We don't want to just whiz through the towns, but stop and see something of note while there.

We'd also like to see Cortona, but not sure how to work it in.

We'd really appreciate any help you could offer as to whether the days are doable or just too ambitious. All our other trip details are long-since planned, reserved and dealt with, but we are still fuzzy on the Tuscany route.

Thanks so much in advance your your help and advice!

Textraveler

Day one looks very doable. Depending on the time of day you are in each place I would recommend Ristorante Lamole or Ristorante Badia a Coltibuono for lunch. Ristorante Lamole is in a little town called Lamole, just south of Greve is a turn off for Lamole, takes about 15 min. to get there, but has some of the most spectacular views of Tuscany along the way.
Badia a Coltibuono is just out side of Gaiole. Both excellent restaurants with spectacular views.

Just a note on Castello di Brolio. You can not go inside the castle but can walk around the grounds. Be sure and go in the chapel and down in the crypt, it is very interesting to read the tombstones. Two tips, you do not have to park at the bottom of the castle and walk all the way up, there is parking closer to the top. Go to the gate entrance and ring the bell, it may take them a few minutes to answer the gate. We almost left thinking it was closed, then someone came and opened the door.

Can't comment on day two as I have only been to San Gimignano and am not aware of the distances.

Day 3 is definitely almost impossible, it is a pretty long drive. I just think you won't be able to do all 5. Maybe Montalcino, Pienza and Montepulciano. Pienza was our favorite town in Tuscany!!

Day 1 looks good, but that's the easiest to plan as that's your Chianti day, and that's where you're staying.

Day 2 is a bit busy, but doable. Remember that stores, etc. tend to close down for the afternoon. I don't remember if that's true for San G. and Volterra, but keep it in mind. You could visit Monteriggioni first; it's a tiny town that's simply cute, but there's not much there to take up lots of your time (unless you eat lunch there). Then on to San G., spend 1-2 hours there, and have lunch in San G. Then on to Volterra, where you could also spend several hours. The Etruscan museum there is very good.

Day 3 is too much in one day. I would suggest Montalcino, Pienza and Montelpulciano, especially if you're interested in wine. Arezzo I haven't been to. Chiusi is a nice enough town, but not on par with the others listed for this day. Cortona is also a good visit, but I don't know where you'd fit it in either!

Have a great trip - all of your possible destinations will make for a wonderful time.

Re: Day 3 - You're an hour and a half from your first stop which would be Montalcino. I think it's tight but feasible to then visit S. Quirico, Bagno Vignoni, Pienza, Monticchiello and Montepulciano in that order. Coming back to your headquarters, I suggest getting to the speedy road S326 toward Siena. No Arezzo or Chiusi. BTW, what about Siena - aren't you going there?

You have a good start but forget anything east---Cortona, Chiusi, Arezzo etc. Your day 3 will be full with the Mont. towns and Pienza. That will be a good day if you get off by 0800 and plan well.

I agree with others' comments - much too much for day 3. Personally, I like to slow down and relish my vacation. I even think Montalpuciano and Pienza and enough for one day if you linger over lunch and take into consideration the long afternoon closings. You'll love southern Tuscany!

Hi Tex,

I agree with the others, especially about day 3. No way could you do all the towns mentioned.

I would HIGHLY recommend fitting in a visit to Sant Antimo Abby though. It's just a 10 minute drive from Montalcino. Be sure to go when you can hear the Gregorian chants. They actually have their own web site (Italian only) giving the service times. This was one of the real highlights Oof my last trip.

Buon viaggio!

Thanks, everyone! I was hoping for some magic solution to allow us to do all of the Day 3 scenario, but alas...

Sort of like being limited to only three scoops of gelato, when you have an entire array of flavors to choose from!

to Jgg: Thanks for the restaurant and parking recs.

to Lexma90: I've been reading that the stores and sites in San G are staying open all day these days. We do plan to pass thru Monteriggionni for a quick view - thanks for the reminder!

to TuckH - we've been to Italy three times and have seen Siena before, but never any outlying towns in Tuscany

to Bobthenavigator - We will stick with the three cities you recommend

to Dorkforcemom - thanks for the reminder to take it slow. I just wanted to see all the towns. Guess I'll just have to come back for a Tuscany-Umbria-only vacation, eh?

to Dayle - we will squeeze in a visit to San Antimo Abbey; have read many recs for it.

We will take everyone's advice and stick to Pienza, Montalcino and Montepulciano for Day 3. I'm glad you all give your blessing to days 1 and 2.

Thanks to all - textraveler