Safety driving in the hill towns of Tuscany.

Most European hatchbacks and small station wagons (which are the majority of cars) have rigid panels that lift when the rear hatch is opened and that provide a visual barrier to anything that may be stashed behind the rear seat.

I've seen thieves slowly cruising parking lots, when they think no one is watching, looking in car windows trying to determine which one is worth the effort to break into.

If things work out terribly for you and your car is built such that stuff in the back is visible, stop by a housewares store and buy a black flat bedsheet (un lenzuolo, if my Italian dictionary is correct) and carefully drape it over the contents, making sure everything is covered. From the outside, all a thief would see is black. In other words, nothing interesting.

That's 20€ or so for some peace of mind. Not a bad bargain, in my opinion.

This advice is only for short term stops, such as at a tourist site or a restaurant. For overnight stops, haul everything out. Leave nothing in your car of any value.

We drove around the Tuscan countryside last summer in a hatch back rental with no problems. As previous poster mentioned, the hatch backs come with a 'cover' so that your stuff is covered. We drove from Pisa to Cortona with a day stop in Volterra--with all of our luggage--and had no problems. We parked in Volterra's parking garage, placed the hatch back cover over our luggage and spent a lovely day in the town. I would not, however, leave anything in the car overnight. Have a great trip!

What would you do if you were traveling in your State?
I’m asking because I lived in Italy half of my life and traveled to it yearly during my other half life and nobody broke into my cars. On the other hand, during the half life in California my cars were broken into at least 6 times in public lots (mostly at transit stations).
Statistically I wouldn’t consider Italy higher risk than the US, especially in small villages like in the Chianti where theft is very rare. Hatchback cars have cargo covers, so they aren’t inherently more vulnerable than sedans.

Having said that, I wouldn’t bother to change hotels in your case. I would stay in the same place in Siena and return to it at night. San Gimignano to Siena is maybe 45 min drive, shorter than my daily one way commute to work. Probably shorter than the time you’d waste repacking and checking out of your Siena hotel.

On the way back from San Gimignano to Siena, see if you can stop In Monteriggioni for a quick visit. You have to pass by it anyway, and it’s worth it.

If you want to visit Volterra the day after, before heading to Montepulciano, and don’t like the idea of having luggage in the car, check out of your hotel in Siena, then leave the luggage at the hotel. Drive to Volterra and visit Volterra till the afternoon. It’s only one hour away. You have to pass by Siena again to go from Volterra to Montepulciano. On the way back from Volterra, Just swing by your hotel to pick up your luggage, then proceed to Montepulciano. Not a big deal. Just an extra 15-20 min.

mk,

You may be aware of this, but be sure to have an International Driver's Permit, as that's compulsory in Italy. That's used in conjunction with your home D.L., so you'll need both. Also be very careful when to avoid driving into the ZTL (limited traffic) areas that exist in many Italian towns (hefty fines!).

It really does not matter if it is a hatchback or not. Thieves can break into a true trunk as well--the pros have machines that pop the trunk. Rental cars are easily identifiable. This is just a risk I have accepted, but I tend to travel in rural areas. Anecdote does not equal data, but I have left my luggage in the trunk in parks and other remote places. Of course do not leave anything truly valuable or important, but then again, losing all of your clothing on a vacation is bound to be rather depressing at the very least.
Honestly I would never consider it a risk under similar circumstances in the US--why would anyone want dirty clothing? But there must be something in it for them...

What time of year is your trip?

My suggestion is to follow your plan of driving SR222, then driving over to Volterra getting there mid-afternoon. Spend the rest of the day and the evening exploring Volterra after you've checked in. Depending on when you want to get to Montepulciano, explore a little more in the morning, then head towards San Gimignano. Explore it for a few hours before heading down to Montepulciano. If you drove straight through, it's only 1 1/2 - 2 hours from San Gimignano to Montepulciano.

There is a large parking lot just outside the main gate into San Gimignano. It is in a busy area and I don't think it would be easy to break into a car without being noticed. I appreciate your concern and desire to be careful, but I think that too often Italy is depicted as a den of thieves and folks become overly concerned about the safety of their possessions.

Hertz gave us a nice Peugeot diesel SUV for our rental car. We called her Deedee, since her passenger door had a big dent (dented door). The dent was properly documented before we left. Deedee had tinted windows and a cover for the storage area. It was really hard to see if there was anything stored in her. We left her in a public lot in Greve from 6:15 in the morning to 8:15 at night when we took the bus into Florence. We had no problems.

How many are in your party? How much luggage are you taking?

Thank you all for the information and especially regarding the coverage in the cars. I feel more comfortable driving with the luggage during the day, especially stopping in the little hill towns.

Dougmac, we will be in this area around the third week of September. I am thinking of doing what you suggested, after the SS222 drive, going straight to Volterra and checking in there and then spending the rest of the day and night there. Then the next morning stopping in San Gimignano and possibly a quick stop in Monteriggione.

There will be 2 of us traveling. As far as luggage, I know Rick Steves recommends each use a carry on size. Since we will be in Switzerland the week before coming to Italy, I am not sure if we will be able to fit all in such a small suitcase as we will need warmer clothes for Switzerland but we will try. Otherwise we thought possibly each having a backpack along with the carry on size (which we would then check in), otherwise a medium piece for each, which now thinking may be to big to fit in the area in the car that covers up the luggage. Any thoughts on that?

In looking through some guidebooks for accommodations, some mention in town and a few within walking distance outside of town, which do have parking for those driving. Rick Steves mentions the steep climb into town if you stay outside (we are fit people that do hiking in the mountains), but would you recommend staying in town? I am sure there is a parking lot right outside also, right? Any suggestions of places to stay are also appreciated. Thanks all!

I drove to Volterra and chose Rick's listing for the "handy for drivers" La Primavera B&B, which is very close outside-the-wall (about one US block from Gate/Porta Fiorentina), with parking at no extra charge. It was a nice place to stay and also probably a better fit for my budget. The next-closest inside-the-wall hotel (La Locanda) is also at the bottom of the hill, so not much different in terms of walking between the hotel and the central square.

On the chance of a car being broken into, strategies include 1) taking valuables with you and 2) possibly leaving those hidden bags unlocked and easy to search, so thieves can see for themselves that you did take valuables with you.

You'll be there at a wonderful time of year. Check to see if there are any harvest festivals nearby, especially if you are there during the weekend.

We've done a number of 2 week trips, but not a 3 week trip. We have used our trusty RS convertible backpack. I'm not sure being able to do 3 weeks out of carryon unless you are hardcore. Maybe you could do two carryons and one checked bag, so just one of you has to do the heavy lifting. If you take two checked bags, I don't know if you've heard of the trick to put half your clothes in each bag in case one gets lost. That way both of you will have some clothes.

I don't think you can go wrong staying either in or out of the walls. As you mentioned, the places are easy walking distance. We strolled from one gate to the other in less than an hour and we were taking our time. The next time we go back to Tuscany, I dream of staying in Volterra. My dream for that trip also includes two weeks in Rome.

There is a large underground car park just outside the main gate. You actually walk up a staircase into the town. Be sure to hang out in the evening just outside the main gate. You'll be treated to the townsfolk taking a stroll. There will also be a spectacular sunset. I took a photo of the town bathed in a warm sunset glow which is now the wallpaper for my phone as well as a large print in our house.

Thanks again for your replies and suggestions. The Primavera B&B was what I was looking at so good to know that it is a quick walk into town. Hopefully we can get a reservation there. Also excellent suggestion about dividing our clothes among the two checked suitcases. Great to know that you want to go back and stay in Volterra as it is reassuring to us to stay there. Thanks!