Driving through Tuscany: Pienza, Montalcino, Montepulciano & Chianti

Most, if not all, of those cities (including Siena's, which are monitored by cameras!!!) have limited traffic zones. I went in with a rule of thumb to not drive into ANY towns because like you, I was nervous. Rick's book does a great job of showing/telling you where the parking lots outside the city centers are. In all of those towns you mentioned, there is easy parking all around the town centers that is really well noted with signs. we just followed the BIG P signs, drove slowly, and had no problem. Same for Siena! I was really nervous too, but following Rick's advice for parking lots and using a GPS, I was able to all of the dreaded ZTLs. Driving was actually quite a pleasure! You already have a great list of towns there. My travelmate and I quite enjoyed our tour of the Castel Brolio, which included a free chianti taste. Also, I wouldn't miss Volterra, which has a great Etruscan museum, interesting alabaster workshops, a Roman amphitheatre, and is all-around beautiful. Certaldo has an interesting little old town, as does Colle di Val d'Elsa.

Stephie,
See http://www.slowtrav.com/italy/tuscany/hs_planning.htm

Stephie, my husband and I did this last September. Once you are out of the city, the country roads are easy to use. Getting into and out of Siena was the worst, so I recommend you find a place to park near the edge of town within walking distance to your hotel. We wish we'd ordered the optional GPS--when we picked up the car there were none available. We did have a good atlas of Tuscany.

We drove to Panzano, on a hill above Greve in Chianti, and met world famous, larger than life butcher Dario Cecchini and his American wife in his shop/ restaurant. His food and store are amazing. It was one of the highlights of our trip. You probably know there is a government wine tasting room in Greve where you can tase over 100 different types of wine. We spent several hours and bought great souvenirs there. Driving to both of these towns and to Montepulciano from Siena was easy.

Driving within Siena was a nightmare--streets that look like they go through on the map don't--the last 100 yards are a stairway or one-way in the wrong direction. We went round and round for 1/2 an hour just trying to get out of town and onto the road, as well as back in and turned in the car early.

We avoided the dreaded ZTL's by reading all about them on this site, watching for the signs and parking on the outskirts of towns.

Montepulciano is VERY steep--it felt like mountain climbing after parking at the very bottom.

Sometimes you just have to ditch the car and get a gelato. We loved hanging out at Il Campo in Siena during cocktail hour and gladly paid the drink prices for a ringside seat at an outdoor cafe during passegiata to watch the parade of people going by--Buona vacanza!

Stephie, There is plenty of parking in Pienza, only a short walk from that magnificient walled city, look for the signs. Montalcino has adequate parking as well. Montepulciano is a wonderful place to explore, and while it is a little step, there is a shuttle that will take you to the top, and you can take a slow walk back to the bottom. Make sure and venture to the walls and take a look at the surrounding countryside. It is awesome. The driving in the surrounding countryside is easy and a wonderful experience. Watch out for tailgating, that seems to be a requirement for Italians. Worst of all are the motorcycles, one actually reached out and steadied himself on our car, he was that close! We had a hard time finding parking in Siena, but finally found the Roman gate, and there was plenty of places to park. Do NOT try to drive into the city. Wow, sounds like a great trip, I can promise you will love it. Enjoy! Caio, Jeff

Stephie, I forgot to tell you that there is parking right outside the walls of Montepulciano, on both ends. If you can find it, you can drive to the very top, and park in a small lot, onb the left of the city. Enjoy, Jeff

Thank you all for the great information and suggestions! We will definitely look for parking outside the towns.

Stephie, I am so excited for you two! I agree with what everyone has said. As long as you can read a map, or have gps, you should be fine. We took our first trip to Italy in 2008 and are planning our next trip back in 2011. Driving through Tuscany is actually quite simple and can be alot of fun!! Relax and enjoy the beautiful scenery. You will soon realize 3 days isn't hardly enough, so plan to go back again for a longer period. Italy has changed me somehow; I love their culture, their food, wine and their way of simplified living; much different than we in the US are accustomed to.
As far as the towns you mentioned, the only area we haven't been yet is Chianti but that will be in 2011. We did get sort of stuck in a maze driving through Siena,but that's a long story!!
Best of luck; i'm new to this posting page but i'm looking forward to meeting new travel buddies!!

The only thing I have to add is to find out when each town has its market day, the day varies. For instance, I think I recall that Siena's is on Wednesday, and I know that Cortona's is on Saturday. It is great fun to walk through the market, but a lot of locals come into town for market and it can make it harder to find parking. For that reason you may want to plan your trip around when the cities you want to visit have their market days.