car rentals and driving in the Hill Towns

How much luggage?

Probably 4 small carryon suitcases.

Chiusi has a few major car rental companies near the train statin. Orvieto only has Hertz and you must book with them directly to pick up at that office, not through Auto Europe. GoogleMaps and www.viamichelin.com will both estimate driving times. You can drop the car at any town where the same agency is represented, usually for no fee, such as Pisa or La Spezia (closer to the Cinque Terre).

Most rentals have hatchbacks and those are extremely insecure with luggage. No one is fooled by the cover and often the luggage sort of pokes up and makes clear it is there. I would drive to the hotel in Montepulciano and stow the luggage and not be doing hill down visits carrying it. If you do need to stop for lunch or whatever with luggage in the car, be sure you don't open the trunk/hatch at the stop -- do that before you reach the destination and be sure NOTHING is left showing in the cab of the car and carry any valuables with you: ID, cameras, computers. We had such things in messenger bags that went with us even at a rest stop or else one of us stayed with the car while the other went into the rest room.

Of course you know you can't drive into hill towns but they have very well marked tourist parking around the perimeters of the old town usually with giant blue and white signs with a big 'P' on them. Montepulciano is a great base and a beautiful town and in the evening you will have lots of restaurant choices on foot which is nice since the driving limits on alcohol are so low in Italy that the driver really can't risk drinking at all.

I would take the taxi from your hotel in Rome to the rental office of your choice. Each rental company (Europcar and Hertz and Avis are the largest) has many locations in Rome. The locations near the Tiburtina station are really close to the freeways.

From Rome to Montepulciano it's 2 hrs.

I would return the car at La Spezia, the closest location with rental car offices near the Cinque Terre. From La Spezia, after you return the car, reach the station by taxi and take the train. I would not return the car in Chiusi. Too many train changes from Chiusi to Monterosso.
4 adults need a large station wagon (maybe an intermediate, if your luggage is not excessive). A VW Passat Station wagon would work perfectly.
You could also rent two small economy cars. The price would be the same or less..

Thank you for the great suggestions. I think we will need the larger car, rather than two small cars, because only one of us wants to drive. I didn't realize there was so much theft so I appreciate the tips on how to handle our luggage.

Many thanks!

Kathy

I didn't realize there was so much theft.

I didn't realize it either. Because maybe there isn't. It's advice for you, just in case.

I've visited Tuscany over 35 times in the last 28 years, always had a rental or relatives' car. I also used to live in Tuscany (Florence) before then, where I had my own car.

None of my cars were ever broken into, although my bag was stolen from a friend's car trunk while at the Cinque Terre (maybe 35 years ago).

On the other hand, in just the last 15+ years, my wife and I had 3 car break ins at BART train stations in the SF Bay Area and two break ins while the car was parked in front of our homes in two different Bay Area cities here in California. Most recently, two weeks ago, they stole my gym clothes from my car, while I parked near work in the rich San Francisco peninsula (some of those Facebook techies must have liked my Adidas sweats).

Therefore based on my personal crime statistics where I was victim, I must assume there is more theft in California than Italy, however leaving luggage in the trunk is always a risk anywhere. Hence our warnings and advice. If you do intend to leave luggage in the car unattended, do it in a guarded garage, and just leave items that you wouldn't mind to depart from and being donated to the local thieves' community.

I didn't realize there was so much theft so I appreciate the tips on how to handle our luggage.

We were a little concerned before we took our trip to Tuscany. We soon found out that Roberto is right, stories of widespread theft is an exaggeration.

We rented our car at Rome FCO and took a leisurely drive to our agriturismo just outside Greve. We stopped at the Autogrill and had lunch with our luggage plainly visible in the back of the Renault SUV we were given. We also poked around a town or two on the way. We had no problems.

During our stay, we just exercised the same common sense we use in the states. We didn't leave valuables in the car or anything within sight that would be tempting. I took my Garmin which I would stow in the glove compartment, but unless we were going to be away from the car for a long time, such as the day we parked at the stadium at Siena, I didn't even take down the Garmin mount.

I'm much more worried about theft when we visit our son in Silver Spring Maryland than I was in Tuscany.

Thanks again for the advice. I've also had the same experiences as my fellow Bay Area poster--much more theft here than in Italy. Common sense must prevail and then it work out just fine.

Kathy

We did a similar itinerary in reverse last month. From Monterosso we took the train to Pisa. At the main train station, we hopped on the very efficient "Pisa Mover" tram to the airport where we picked up a rental from Hertz. After touring around Tuscany, we dropped the car off in Orvieto. Hertz is right across the street from the train station - we didn't plan that, just good luck. The train to Rome takes an hour.

Don't forget to obtain the compulsory International Driver's Permit for each driver listed on the rental form. These are easily obtained at any AAA office for a small fee and are valid for one year. They must be used in conjunction with your home D.L. so you'll have to bring that too. There was a post on the forum recently from someone who wasn't able to rent a car in Italy without an IDP.

You'll also have to be vigilant to avoid the dreaded Zona Traffico Limitato (limited traffic) areas, as hefty fines will result for each pass through one. Do NOT drive in Florence, as the city is just about saturated with automated ZTL cameras

Thanks again for all the good advice. One last (well maybe not) question is whether we can use Google Maps for driving directions?

We've used Google Maps to drive in Europe with great success - in even the teeniest, tiniest streets in some very small little villages. In fact, she's now called "Googalina, Our Lady of the Dashboard" in our family because she has been such a great travel companion. We bought an inexpensive attachment that allows us to 'clip' our iPhone into the air vent in the car so the map is easily visible; we also put the sound on so the driver can hear the directions. We always get a local SIM card for our phones so we don't worry about data charges but Google Maps uses a very small amount of data. If you are worried about data usage, download the maps for the regions where you will be traveling ahead of time and use the GPS function off line.
We are leaving for Rome in a couple of weeks, taking the train to Orvieto where we will spend 3 nights before picking up a car and touring Tuscany - 4 nights in each of Cortona & Montepulciano and 3 nights in Lucca where we drop the car. The last part of the trip is 4 nights in Florence, 6 nights on a bike tour and then 5 nights in Rome. Googlina will accompany us everywhere - we simply wouldn't leave home without her.

You can use any app that you use at home. Google Maps and Waze both work. I like Google Maps, but Waze has the added advantage that warns you of the upcoming hidden speed camera machines. Since there are tens of thousands (literally) throughout Italy, if you have a heavy foot and want to avoid to have fines in the mail (or your credit card charges, courtesy of the rental company), I recommend using Waze.

Thanks again for the great feedback and advice. One more little question:
How complex will it be to take the train from Monterosso to Milan to fly home?

It's not complicated. Boarding a train in Italy is as simple as boarding a train anywhere else. From Monterosso there are actually Intercity trains to Milano Centrale that require no train change, therefore no reason to be nervous. You get on in Monterosso, and the last stop is Milan, where you get off.
Train timetables are here:
www.trenitalia.com

For a primer on Italian train travel check here. Intercity trains are also described.
https://www.seat61.com/Italy-trains.htm#What%20are%20Italian%20trains%20like

Again, my thanks. Your help and advice have been terrific!