Exploring hill towns with luggage in trunk...

I am not sure what you mean by secure. Even lots with people in booths taking money are not completely secure IMHO. We have driven all over Italy, and really never had truly secure parking. We did use a "manned" multi story parking garage in Mestre, but I still don't think it was really secure. Perhaps they had security cameras, but I doubt it. On the plus side, we were never broken into. The best thing to do (even if there is nothing in the trunk) is to have nothing visible on the inside of the car that can be seen through the window. Other than that, life is a risk (an I don't like it anymore than you!) However, our trips have been worth the risk since we love driving around Europe. I hope you have a great trip and no problems with theft!

A parking lot with attendant is no guarantee, however it's safer than unattended parking. Keep contents out of sight and don't open the trunk at the parking lot, so that nobody see it's full of stuff. If you need to access and get stuff from it, do so before you get to the parking. If you can, back your car as close as possible against a wall or tall bush or tree etc., so that the trunk handle and keyhole cannot be easily accessed and maybe the trunk can't even be opened. That doesn't prevent people from accessing it from the inside, especially if it's a hatchback with seats that recline, but it's a deterrent.

Cat , I'm certain you will get all sorts of conflicting opinions on this so what follows is my personal take on this . Essentially , you have no choice but to utilize the trunk of the car for storage , UNLESS you are checked into a hotel and can leave it there . The key issue is what is in your luggage . I frequently do exactly this and have done so on all my trips . I pack our two small bags of clothes ( 12 lbs each , carry on size ) in the trunk . My wife and I each have a backpack , and anything sensitive ( phones , cameras , CHARGERS , medication , paperwork ,etc ) stays in the backpacks which go with us . The car gets ripped off ? All they get is some clothes . I mean , really , what are you going to do , Schlep every thing around with you all day ? The parking lots are as secure as any place else . One other hint , pack your stuff in the trunk , BEFORE you park so that no one observes you stashing it . If anyone has another alternative , I'm all ears . Besides , agonizing over something as unimportant as clothes or tooth brushes can put a real kink in having a grand time . By the way , in a total of 4 months traveling in Europe over the last three years , I've not had a problem . Doesn't mean that it couldn't happen , but it isn't worth losing sleep over . Have a great trip !!

Leave your clothes, toiletries etc in the car. Take everything else of value with you eg travel docs, any jewellery etc. Good use of a moneybelt or similar, I always use one when moving between places. Replacing your clothes will be a pain but a lot easier than your passport. Also be aware that thieves have targeted rental cars parked in motorway service areas. To date it has been worse south of Rome but can occur anywhere.

Thanks everyone. I'll keep the car clear of anything in sight, pack trunk beforehand, take my necessities in my backpack and go explore :)

Siena is a very difficult city to park in, and it's very hard to negotiate the streets with so many people and apartment complexes. I prefer to go there by bus from Florence, which drops you off in the middle of the city. Staying in the countryside outside San Gimignano or Certraldo is a central location to do day trips out of to places like Volterra. Booking.com represents many properties in the area.
Working out of a central location will let you not carry luggage in your car. It's best if you travel light enough where your luggage can all fit into the trunk out of sight.

Thanks David. Is it pretty easy to leave the car in a parking lot outside Siena if you're staying in town? I imagine it could be expensive. Plus dealing with your bags...
I'm still tossing around an agriturismo outside town, or a hotel in town...

We stayed in an Agriturismo just outside of Siena. The day we spent in town we parked outside the walls and walked into town. It was easy to do that. Other days we drove to hill towns.

Hi Andrea!! :)

Over a period of 30 years we've driven extensively in Europe, mostly in Italy. We've been broken into 3 times. Once in a lot in Avignon, twice in remote area of rural Italy. Thieves want fence-able stuff so they will rifle through bags quickly looking for jewelry or a camera, etc. They don't want your socks. We carry a bike chain with a combo lock and chain the bags together to encourage rifling not removal. Then we unzip many of the luggage compartments. Obviously we do this before we park. Then we don't worry about it. It's unlikely and it would be a relatively small hassle, certainly less hassle than some arbitrary stranding by your airline.