Driving in Tuscany and itinerary help

There are several Frommer's books about scenic drives in Italy that you might benefit from taking a look at. One is Frommer's Italy's Best-Loved Driving Tours and the other is Frommer's 25 Great Drives in Tuscany in Umbria. I recommend you avoid booking a tour and just hit the open road by yourselves. It's a lot of fun, and no more difficult than country driving anywhere in the US or UK. The roads can be a bit serpentine at times, so just go at your pace, and don't get flustered if the locals tailgate you, wanting to go faster. They know all the best places to pass you, believe me. Don't waste the days you have with a car on San Gigmignano, Volterra or Arezzo. They're easily reached by bus or train from Siena or Florence, and your car would just sit in a parking garage or lot most of the day. Use the days you have a car to visit places like Montalcino, the abbey of Monte Oliveto and the Colli Senesi... having a car is your big opportunity to see all the special little things that most tourists don't get out and see.

Do you mean that you have two full days to visit Florence (3 nights), or 2 nights in Florence, which equal one full day plus (probably) part of another day? And the same question for spending time in rural Tuscany (remember that Florence is located IN Tuscany). If so, either way, that's not a lot of time for either place, especially as you're also visiting Rome, Venice and the Cinque Terre in the same two weeks. In any event, I would suggest that you rent a car for your two days or nights in rural Tuscany. It's much easier to get around that way, even Siena and San Gimignano, if you choose to visit those cities. There's no need for most people to take a tour to visit the area. I don't find it difficult to drive in Tuscany. The signage is quite good (much better than a similarly-rural area in the U.S.); some roads are winding with little shoulder, but they tend to be well maintained. If you were comfortable driving in the UK (on the opposite side of the road), then you'll be fine in Tuscany. Depending on your itinerary (i.e., where are you fitting in the Cinque Terre), you could pick up a rental car as you leave the Cinque Terre or as you leave Florence. If you like Chianti wine, drive on the s222 through that area. You'll only have time for a couple of towns; all those you mentioned are lovely. Though Montepulciano is pretty far south, and would make the most sense if you drove from there on to Rome, though worth your time especially if you like their wine. And Montalcino, of course if you like wine. Florence is worth your time if you like Renaissance art; if you prefer more rural areas, then skip Florence this trip and focus on the rural areas - it depends on your interests / preferences.

Driving is part of the fun while in Tuscany. You can visit and stop whenever and wherever you please. Stay in Siena. There is a Hertz rental agency right next to the train station in Siena. Pick up your car there and include a GPS (well worth the addtional cost)and go. A car will cost you roughly $200 a day. Pick a city and enjoy the drive. One day go south and the next day drive north. Every stop is a new memory. Have fun.
RDB

I signed into Hertz.com and got a $50 rate on my Gold Card. Join their club. Check AutoEurope.com to see if a cheaper is offered (often on a Hertz car.) 1. What is the best way to see Tuscany in these 2 days? Ramble around the countryside. I especially liked Volterra and San Gimignano. Siena was too congested, and parking was too difficult. 2. Do we book a tour? Or do we drive? By all means drive it. 3. Is driving in Tuscany really hard? It's easy to drive, other than the roads being crooked. It's best if you can handle a manual shift. 4. How hard would it be rent a car in a place like Florence airport or Siena and then drive around to visit the towns? Airport rentals are expensive. Take a taxi to one of the Hertz locations in the Florence suburbs. They'll give you directions on how to get to Chianti and south of town.
5. Would it make sense to change our itinerary a bit and instead of spending 2 nights in Florence? No, you need two nights in Florence.

my husband and i had a great time driving around tuscany! it was defintely the highlight of the trip (the cute little fiat 500 had zero power, but we really had a great time driving it all over the place). the lowlight was returning the car to the florence airport, so absolutely rent that car, but rent it at a rental office, not the florence airport. we found a good deal through autoeurope. have fun!!

I agree with most of the other posts that you should rent a car and enjoy. There is no special trick to driving in Tuscany but if you drive in Florence (where we rented a car) plan on getting a ticket for driving in an unauthorized zone. I always try to be careful but almost always get a ticket in the mail a month or 2 after I get back. At this point, I consider it another travel expense! Last time we were in Tuscany we took a day-long tour in a small bus and the next day we rented the car. I think the tour was a mistake...you are totally at the mercy of the tour company, they make stops at places where they hope you will shop (I fully expect they get a percentage of the sales) and you may get stuck for the day with folks who don't share your likes and dislikes. Driving on our own was so much better. We stopped at whichever hill town caught our fancy and we stayed for as long as we liked. Plus, if you get a car with a GPS you can all enjoy the scenery without having someone keep their face in a map! We drove to Montepulciano, among other towns, and we were so happy to have the time to leisurely stroll the streets and not have to worry about getting back on the bus. Yes, a tour guide can be entertaining and informative but hey, that's what guide books like RS's are for! Enjoy. Bob