How to drive / stay 3-4 days in Tuscany?

So many of the lodgings are small with limited rooms which is compounded by finding rooms for three which is a added challenge. Secondly many of these small towns are very restrictive to driving in the center of the town where you may be hotel hunting. You often need to have a special permit from the hotel or will incur large fines often received once you return home.You too may find these medieval roads challenging in a car so people often park in car lots outside as Rick Steves recommends. This then adds to the additional walking sometimes uphills for your mother and you carrying luggage. I think you should quickly decide which towns entice you most. As they are small most can be seen in a day. You may wish to find one lodging only and day trip which could allow some flexibility and you won't be lugging luggage and wasting your time trying to find a bed. You may wish to ask the question on this board of which of these towns are best for your mothers capabilities which will really help you decide.

I haven't rented a car in Pisa. However, generally the airport or the train station is the easiest place to rent. Florence is a beautiful, compact city. However, it doesn't sound like you're enthusiastic about it so I wouldn't stop. Your time would be better spent in the countryside. You could stay about 45 min. south of the city in Castel San Gimignano and from there you could see Volterra and San Gimignano. Then you could continue heading south and stay outside of Siena and take a day to see Siena. Further south we stayed on the outskirts of Pienza. Send me a personal message to get my travel blog website. You could then turn the car in at the train station in Orvieto and take the funicular up into the hilltown and spend the night there. It's one of my favorite hilltowns and is just an hour train ride into Rome. I rent my cars through AutoEurope or Kemwel. You can check their rates online but call them to make final arrangements. Make sure to get your International Drivers Permit at your local AAA office. No test is required. Just $15 and two passport type photos.

Collin, So, we've done this particular drive twice, recently! We met our friends in Pisa, at the airport, and they rented the car there. It was very easy, and very accessible. I could not tell you how far the train station is from the airport, though, but a googlemap would do that. We actually then drove into Pisa to do the tower. The RS book tells you where to park, and we did that and took the bus in to the tower. It's not worth REALLY worth the visit, but it's also one of the those things that I am glad I have done...so I won't have to do it in the future sometime. The drive down does pass "through" Florence. It might be worth going up to the San Miniato church, which has spectacular views of Firenze, if you are not going to stop. We loved our visits by car to Montalcino (did the Brunello tasting), Montepulciano (visited Cantina Gattavecchi for a wine tasting), San Gimignano (for the towers), Cortona (for a hike along a Roman road through the forest) and Siena (for Il Campo). Yes, you can be spontanseous with a car. That's the beauty of the car. I've done Europe three times by car, now, and it's easy enough to drive into town, find the TI, and ask about places to stay. From Siena, the main toll road down to Roma is actually a spectacular drive, one of our favorites, and you can cruise at 85 mph, so you can really do it quickly. Cheers! IM me if you are interested in our blog posts on these places.

Collin, As you're planning to rent a car, I assume you're aware of the usual "issues" for driving in Italy? If you need further details, post another note.

What are the driving issues? I am trying to avoid driving for most of the trip, but this portion seems to make more sense via car due to our time limitations and amount of time when using buses to get from town to town.

The driving issues are: get the International drivers Permit. Buy a Michelin, or similar, map at a Barnes & Noble and familiarize yourself with the signs and roads you want to take. A GPS in the car is definitely helpful. For Siena and Florence, do not enter the ZTL zone because you will incur a fine in the mail. If you follow Rick Steves' directions for getting into Siena (in his Italy tour book) you will be fine. For Florence, you have to park on the outskirts and this would not be easy with your mother. PM me for an idea of where to park. When driving on the autostrada (freeway) always stay in the right hand lane except to pass. Passing is done quickly and efficiently. There are speed camera traps everywhere so mind your speed limits. Parking is never free. When parking in a lot, look for the kiosk. Driving on the autostrada is not free. There are tolls which you can pay in cash or credit card. I prefer to pay cash so I do not incur exchange rate charges. You will be fine driving. We, and many others, have done it for years all over Italy.

Just did this in reverse order. Picked up car in Rome, drove to Tuscany, stopped at Pisa on way to CT, then to Verona. Driving is a snap if you remember that what we would consider laws here are general guidelines in big cities in Italy! We had a garmin and it really helped (except occassionally wanting to send us down the dreaded closed areas!) Italy also does robo camera speed checks, so it was nice to get a heads up on those. As far as your itinerary, we stayed in one spot (castlina) and day tripped around Tuscany. We had two women in their 60s and my nine year old son, so it was nice to have a hub to return to each day. We loved sienna but were there during the Palio. We day tripped to Florence, San g., volterra. Perhaps, you could make a hub farther south, so you could day trip to more cities on your list? Pisa was one thing our son wanted to see, so we went. We can say we saw it. I was sorry not to see the town more itself but we were in the go to get to CT. Good luck!