visiting the hill towns from Florence

We had a car for one day in Florence and did Chianti and Siena. All your rental car agencies are in the Via Borgognissanti (it's actually a street) area of Florence. Check Google Maps to see how far they are from your hotel. They are not out of the city, but they are not in the ZTL or the walking district. You have Avis, Hertz, Budget, Thrifty, Auto Europa and Europcar. Don't forget your IDP, you get it at your local AAA office. If you don't have it they can't rent you a car. Some of the other tourists at my wine tasting got there on the bus to Chianti. Good luck on a rental car, it could be kind of late. If you don't like museums the only two I'm going to recommend are the Academia, visit the Duomo (Basilica di Santa Maria del Fiori) and the Medici Chapel. They don't drag on and on and on. Try to pre-purchase your ticket at this site.
http://en.uffizi-com.waf.it/museo_dett/27-state-museums/3175-uffizi-tickets-reservation.html

If you can do a group tour, your hotel or the tourist information office (right across the street from Santa Maria Novella train station) will probably be able to accommodate you - the cost of the tour would be about the same as a one-day car rental. All the towns you mentioned are accessible by bus or train.

Be careful with driving while wine tasting. The laws are much stricter in Italy. We hired a driver to take us to wineries, that way everyone can taste and not worry about driving.

Since you're into food and wine, strongly recommend that you plan on spending most of a day at the verrazzano winery-they have a spectacular 3+hour mid-day dinner with a flight of 5 wines and Grappa near Greve in the Chianti region along with a tour of the winery(www.verrazzano.com) My DW had the vegetarian courses and they were unbelievable while I was more on the carnivore side. You are at a banquet table with others and it is wonderful!

My husband and I just returned from France in April and did not need IDP, nor did we need one in Italy 5 years ago. However, the rules may have changed. Renting a car was great (have done the trains, too) but, parking is always an issue. The trains are fabulous because it leaves you the time to SEE where you're going rather than navigating and getting lost. Just study a schedule before heading out. We loved the small villages of Montepulciano and San Gimignano as well as, Volterra. Sienna is beautiful but, big. Adamo, at Cantina Contucci, was quite hellpful with wine tasting and tour of the cellar..the wine was fantastic too but then it all is when you're in Italy! It was not in the least bit crowded which added to the ambiance. And, if you don't care for museums (neither do we) then just walk through a couple of the MANY ancient churches...architecture, paintings, stained glass, all stunning. The roads between these small villages are winding, beautiful, twisting and turning through the mountainous Tuscan Hill country. Volterra was full of ssurprises! AN ancient Etruscan hill town with it's own rediscovered Roman theatre, a great market and very windy. The markets are my favorite for picking up inexpensive wine and picnic lunch items. Views are phenominal!...as well as in San Gimignano though we liked Volterra better. (And that was before the infamous Twilight Series of books). RS walks are usually informative and fun so, check those out, too.
Didn't mean to get so long winded, sorry. Have a wonderful trip.

Just wanted to add to what Julie said, Italy's limit is .05 (compared to a .08 in most US states). Fines and possible jail time can be intense. If the point of your car rental is to visit the Tuscan countryside and wineries, it would be easier to go with a tour. If you want a car just to drive around and explore, then a car might be a good option. Just consider your priorities! If you want to visit Siena, it is easily done by bus from Florence. Other ones are a little trickier, but still doable with public transportation.

Any advice on how to do a day trip by bus both ways from Florence to Siena would be appreciated. Also, what highlights in Siena would you recommend as we won't have time to see everything. Also, we do walk a lot. Can you walk around parts of the medieval wall?
MEC in Michigan

If you are not that into museums and want to do the wine country and cooking classes in villages why are you staying in Florence for 5 nites? I would think about staying in one of those smaller villages with a car, then make a day trip by bus into Florence. From all the places listed it appears you will be having the daily hassel of trying to get out of Florence. There are so many wonderful areas to drive and explore in Tuscany that seem more well suited for what you want. I always have a car and have taken day trips into Florence but prefer staying in the villages. I am not saying you should skip Florence, but you can see a lot of it in a day if you skip most museums. I always get my car at the airport in Florence and head right out of the city, being careful about the zones.

Margarette,
http://www.sitabus.it/sita-toscana/Firenze-Siena2010.pdf See the campo where the palio is run. Palazzo Pubblico, town hall, has Sienese art including Ambrogio Lorenzetti's Good and bad Government. Climb the Torre di Mangia for a breath taking view of the city. The duomo is has a great exterior and is filled with works by Donatello, Bernini, Michelangelo, and Pisano as well as containing the Libreria Piccolomini. Even the floor is covered in art. The bapistry and crypt are beneath the Duomo. Spedale di Santa Marie delle scalla is a 1000 year old hospital that has huge works of art. The archaeological museum under the hospital. Museo dell'Opera del Duomo. The above is only part of what you can see in two of the piazza. There is much more.

Hi Amber: I spent a week in Florence last month with my wife and young daughter. Before leaving the US I booked a one-day tour to various Tuscan towns, including Siena and San Gimignano. We also rented a car for another day and expored on our own. In my opinion, the tour, while nice, just wasn't worth the expense. We all had so much more fun just being in the rented car, making our own itinerary and seeing what we wanted to see. Sure, the tour stopped at a winery for a look around and lunch, but that was mostly a way for them to sell wine and olive oil. Also, you are driving in a relatively small van and if some of the others on the tour are not a good 'match' it could be a very long day. Next time, we will skip the guided tours and spend more time in control of our own sightseeing. Be sure to download the RS podcasts...

For a rewarding side trip that takes little advance planning, take the local bus to Fiesole, a hill town above Florence. It's the ATAF Florence city bus Number 7, departing from the main train station. There are two or three bus companies operating out of that area. I think the Fiesole bus departs from the westerly side of the train station. More at http://www.fiesole.com/