visiting Tuscany

I think it would be difficult to find one town from which you could visit Lucca and Montepulciano (the towns in your list that are the furthest north and south, respectively). Where does your tour end? I assume that's where you'd pick up your rental car. Actually, I'm also assuming you'll have a rental car! And where do you need to be at the end of your three days in rural Tuscany? If your tour ends in Florence, then you could pick up your rental car, head west to Lucca, then drive on to your lodging for the three days. If you did that, maybe consider a location that's further east and/or south than Volterra, as that's the furthest west of your other locations. I really like staying in San Gimignano. Yes, it's full of tourists during the day, but in the evening and early morning, it's delightfully quiet. The main piazza has a couple of cafes and two fabulous gelaterias, so it's a great place to people-watch in the evenings. No other towns that you "must see." You probably already have enough to fill your time. Volterra has a good Etruscan museum, as well as an interesting Roman theatre on the north end of town that doesn't get enough visitors, IMHO. And if you like Brunello wine, you can spend time in Montalcino tasting wines at various enotecas. Or even tour a winery or two.

We have never been to Volterra and Lucca, but I have heard only wonderful things about them! However, we have been to all of the other towns you mentioned. Driving all over Tuscany is just a joy; it is SO beautiful, I would think Volterra would be a great home base. There are SO many wonderful hill towns in this area, you don't want to spread yourself too thin, but some of them you won't need more than a couple hours to see most things. Do some research in Rick's Italy book on the towns and you will get all of info you need from him! WE LOVE RICK STEVE'S!!! We will also be in Italy from 5/25 - 6/12 this year spending about half that time traveling in and around Tuscany.
HAPPY TRAVELS!!

We just got back from Italy last night and went to most of the towns that you mentioned. Volterra is a beautiful hill town and would be my preference over San Gimignano if you plan to visit the northern towns. With only 3 days you might want to focus your trip to one area. Montepulciano would be a great choice to base if you wanted to do the southern towns such as Cortona one day and Pienza and Montalcino the other. If you have another full day to day trip you could also do Oriveto.

Too many towns, too much driving. Have you driven in Italy? I have not, I've only ridden in a car with friends. They had lived in Italy for a year and had traveled the routes many times....and they were STILL confused by the roads! Here is what we're doing: Arrive Milan-overnight Cinque Terre - 3 days Tuscany Farmhouse - 5 days Chill... http://www.airbnb.com/rooms/6913 Florence - 5 days Tourista stuff Bagni Di Lucca - 2 days, visit Lucca (Rent a car, drop in Milan)
Parma - 1 day Milan - 3 days Fly home. That is a 21 day trip that will be relaxing. One thing I learned. Many talk about how challenging navigating around large towns can be. Very small streets, traffic, tool roads, yada yada... We finish 5 days in Florence and I was going to rent a car and drive to Bagni Di Lucca. ...but after thinking about it, and checking out the cost (the same...) I'm going to rent the car in charming, relaxed Lucca instead. We'll take the train to Lucca for 12 euros and not hassle with traffic in Florence and toll roads. Many people enjoy lucca, and we're looking forward to it. We got great rates at a hotel in Bagni Di Lucca, the Corona. It's only 10 miles from Lucca. Couple nice restaurants, including one at the hotel. If you spend much time on these boards I think you'll figure out that you need to cut down the number of towns. You could easily eat up two days enjoying Lucca. You're from Idaho. I was born in Montana. We're used to driving long distances to see things. It's not like that in Italy. Distances are smaller, but driving is not as simple. Half the enjoyment of Idaho or Montana is driving through it and enjoying vistas. In Italy, enjoyment comes from relaxing in a small town and soaking it in. You can't do that at 100 Km/h.

Our tour ends in Florence; we were thinking of renting the car at the train station there, as we will be going on to the Cinque Terre after our three days in Tuscany. Thinking that we would bring the car back to the train station (if it's even possible to rent a car there!) and then take the train up to Cinque Terre. Does this sound like the best way to do this, or any other ideas?
Camille

We finish our five days in Florence and head to Bagni Di Lucca from there. I was going to rent in Florence like you planned, but after reading all the chatter and thinking about it, and checking prices (they are the same....) I'm going to take the train to Lucca and rent the car there. MUCH more relaxed, I'm out of Florence, don't need to pay the tolls to get to Lucca, etc. The train to Lucca is 5.80 euros each. I'm booking a car at Hertz using Kayak.com. $57 a day for a itsy bitsy teenie weenie clown car. Pick up in Lucca and drop in Milan. If I were you I would Rent and drop in Lucca, or rent in Lucca and drop in La Spezia perhaps. I just checked, you can get a 3 day rental for $57 a day at Hertz doing what I just said (Lucca p/u, La Spezia Drop) That's what I would do. After reading my previous post, I realize I repeated my incredibly wise advice. Sue me.

Ted - I love your incredibly wise advice; keep it coming! No, seriously, it's not a lot more expensive to pick up the car in one location and drop off in another? I'm beginnning to like the idea of getting out of Florence and getting the car somewhere else.
Camille

Ted
Good info from your Italy itinerary. Wondered if there was a particular reason for spending 3 days in Milan. Your other destinations are awesome and I was not impressed by Milan. Unfortunately, most of the buildings are post WWII because of the destruction. Of course, there is the Teatro alla Scala for opera and Da Vinci's "The Last Supper" but that won't take 3 days. You might want to consider spending another night or 2 in one of your other destinations. Otherwise sounds wonderful!

Camille - rental car offices in Florence are some distance from the train station. Better to get out to the airport and pick up there. Driving in Italy is easy. You have identified some long trips for only three days, though. With a rental car, I'd suggest basing in an agriturismo (free parking) between Florence and Siena and seeing Montalcino, San G., Siena, and possible Montelpulciano. If you do, don't try Lucca (I love Lucca, though) or Cortona. Not enough time.

With everyone's great feed back, I think I'm changing our plans! How about taking the train from Florence to Siena (my husband really doesn't want to drive in, around or near the city!), renting the car in Siena, booking a room somewhere on the outskirts of Siena (Rick Steve's mentions several in his Tuscany book) and traveling out from there. Might have to skip Cortona, it looks to be too far away. Can stop at Lucca on the way up to Cinque Terre (train from Siena). Thanks for all the super info so far, I really appreciate it!
Camille

@ Bobbi: Reasons for three days in Milan: Actuallismo, we should break this down. We are spending three passion filled nights in Milan. A Friday, Saturday, and Sunday night. We leave from MXP at 7:10 AM on Monday morning. So, Sunday night is going to be a very short passion filled night. No laughing, please. Sunday night is REALLY short. So, we arrive Friday. Friday afternoon, after I've spent Friday in Parma stuffing my cheeks with all the prosciutto and parmesan they can hold. I expect to collapse in our room Friday in a prosciutto and parmesan induced coma, only to wake up watching reruns of Perry Mason episodes dubbed in Italian. That leaves Saturday. On Saturday the object of my desire wants to go shopping in Milan. I hear it has something remotely to do with Fashion. Don't ask me, I'm trying to recover from a prosciutto and parmesan induced coma. Pass me the foccacia, grazie. Truthfully.......(never trust a man who says truthfully.....) we're at the end if a 21 day odyssey in Italy and it's all about the approach to MXP at 7:10 am on Monday mornng. So, I'm not going all "Rick Steves sees 20 cities in 20 days!" at this point. But that's just me. :D

@ Doug in Portlandia, This is how I chose to pick up a car in Lucca as opposed to Florence. I had two choices: 1. Getting to the train station in Florence, which we were close to, with our bags then taking the train to Lucca, and picking up a car there... 2. Getting transport to the rental car office near the train station, about twice as far as the train station, then getting a car, then navigating to Lucca and paying tolls and for gas, etc... It was an easy decision to take the train to the more relaxed Lucca and get a car there. I've driven from Amsterdam to Paris, drove in and around Paris for a week. I've driven in Munich. I've driven from Geneva to Flan, a ski area near Chamonix, and through the Mt. Blanc tunnel to Italy.

Ted- you crack me up! I love your "Parmesan and prosciutto induced coma!" and, of course, the "passion-filled nights!" I hate to finalize our plans and end this fun commentary Any comments on my last trip-related ideas?
Camille