Renting a Car for the first time in Italy

Suggest reading the Rick Steves info about car rentals in Europe under Driving on the Travel Tips section of this site
https://www.ricksteves.com/travel-tips/transportation

The only major car rental company that Google Maps shows at Camucia is Sixt. You may have to book directly with them, as it appears they are not represented by Auto Europe. You could return the car to any Sixt location in Italy. It pays to book ahead to get the size and price of car you prefer, rather than being charged for a big car when that's all that's left. Car rental reservations usually have generous cancellation policies. For just a few days, I think you might as well divide up the duties with him driving and you navigating.

Rented one for the first time this Sept and driving and the rental process is not hard. Make sure to read up about ZTL zones, go to AAA to get your DL from the states translated into an Internal Drivers Permit.
Ok to do just for your DH if he will be the sole driver. It adds a daily fee to have more than 1 driver anyway.

I used and would recommend Autoeurope.com
I would look at the site for the options and then call so you are somewhat knowledgable first rather than blindly calling, they are a consolidator so sell different brands, stick with something from Europcar, Hertz or Avis ; avoid the others. We used Europcar and had a positive experience.

You will get a manual unless you pay a good amount extra and insist on an automatic.

Keep in mind small cars in Italy are much smaller than small cars in the US. What they consider mid size or intermediate you likely will think is a compact, it will just be a better grade of car rather than a physically larger car in many cases. For comfort reasons you might not want to go with the lowest cost option and also look at the luggage space.

Usually best to rent from a larger city where there is competion, for your trip I would rent as you are leaving Florence right before or after check out. We used the Florence city office of Europcar for pickup and it was painless. We had stayed in Florence and when leaving town went to the office and drove out of town just follow their instructions on getting out without going into any ZTL zones. It will be fairly straight forward.
There are a couple of Florence offices, this is the one we used and was good for driving out of town plus a short walk from the train station area and most attractions in Florence.
Via Borgognissanti, 55/red

The countryside you do need a car to explore properly, some of the roads can be narrow and curvy so you need to pay attention at all times but driving around is not a problem.

At the back of Rick Steves travel books he has driving symbols that you should familiarize yourself with. It is nice to understand those symbols before you go!

When we were in France there was no one on the road and we ran across a symbol we didn't know. We stopped so I could looked it up and found it's meaning: NO STOPPING! We had a good laugh.

We use Sixt and book directly with them, always.

We plan to spend the first few days on our own exploring Cortona without a car, taking the train into Florence for a day or two

Cortona is pretty small. We thought a day in the town proper was enough to see everything.

I agree about the size of Cortona, but you could certainly take multiple day-trips to Florence which is about 90 minutes away with approximately hourly service. Orvieto's worth at least a long day-trip. It's about an hour by rail, and the trains run roughly every 2 hours.

If heading away from Cortona by train, you'll need information on bus transportation from the hill-town of Cortona down to the train station of Camucia-Cortona. One of the first things I'd do upon arrival would be get hold of that bus schedule! Be careful about weekends and holidays; service may be infrequent. It is not safe to assume that the bus in synched up to the train schedule, though it may be. I assume taxi service is also available to and from the train station if it's inconvenient to wait for the next bus. Carry the taxi telephone number(s) with you in case you want to summon a taxi to the train station.

If you use a GPS at home take it with you if you can get European/Italian maps for it. You do not want to be trying to figure out a strange GPS.

all,

As the others mentioned, you'll need to be aware of a few "caveats" when renting cars in Italy, and also when using public transportation such as trains. A few points to mention on your travel plans....

• As stated above, your husband will need the compulsory International Driver's Permit which is used in conjunction with your home D.L. These can easily be obtained at any AAA / CAA office for a small fee and are valid for one year.
• You'll have to be extremely vigilant to avoid the dreaded ZTL (limited traffic) areas which exist in many Italian towns and cities, as hefty fines will result if you pass through them. Do NOT drive in Florence, as it's just about saturated with automated ZTL Cameras. There are other pitfalls such as driving in Bus lanes to be aware of, and also automated speed cameras on the motorways including the devious Traffic Tutor system. You may find THIS website helpful.
• You'll also need to do some homework on using public transit. When riding Regionale trains using locally purchased tickets, you MUST validate the ticket prior to boarding the train on the day of travel or risk hefty fines, which will be collected on the spot. The same applies for Metro, Buses, etc. When riding on the fast trains such as Freccia and InterCity, tickets are specific to train, date and departure time and can ONLY be used on the one train listed on the ticket. If you board the wrong train by mistake, you'll be deemed to be travelling without valid reservations and again probably fined on the spot. On those trains, your seat reservations will specify the coach no. (Carrozza) and seat no's. (Posti) where you must sit.
• Two stations serve Cortona, Camucia and Terontola. Of the two I prefer Camucia. You'll need to use the Bus to get up to the town (I can't recall if the driver sells tickets). For the trip down the hill, there's a convenient Tabac shop on the road just below Piazza Garibaldi, and you can buy tickets there.
• I agree with the others that two nights and one full day is probably adequate for Cortona. However, it that's going to be your first stop it would probably be good to add one night to allow more time to get over jet lag. Which airport are you flying into?
• If you're going to have the car for even a day or two during your time in Cortona, as I recall there's a convenient car park just below Piazza Garibaldi on Viale Cesare Battisti. It's easy to get up to the Piazza from there as there are two Escalators (assuming they're working at the time). The car park is free AFAIK but you can check with your hotel on that.
• If you haven't alread, I'd highly recommend packing along a copy of the RS Italy guidebook as there's an enormous amount of information there that will help your trip go smoothly. The 2017 edition will probably be released in December, but it probably won't differ too much from the 2016 edition.

Good luck with your planning!

Where will you be before going to Cortona? Rome, Florence? You could pick up a rental from there and drive to Cortona. Also, where is the apartment exactly? Does it have parking on the premises?
Cortona can be visited in a half day, so having a car for your entire stay will greatly enhance your ability to visit several towns nearby, e.g. Arezzo, Anghiari, Castiglion del Lago, Lucignano, Montepulciano, Pienza (just to name the closest ones).

We just returned from a month in Italy and France. I rented cars in both countries through Kemwel which is a consolidator. In Italy it was a Fiat from Hertz at the Florence airport and at the Nice airport a Citroen from Autoeurope. No problems with either experience. I highly recommend you rent a GPS through Kemwel if you don't have an up to date one yourself. They will ship it to you a couple days before your departure and you just need to send it back when you return. Ours did an outstanding job with verbal directions as well as a map showing which road to take out of a roundabout on the display plus a readout of your speed and the speed limit.

No to confuse the OP anymore but wanted to mention regarding GPS since it has been mentioned a couple of times.
Before our trip I bought a Tom Tom with European Maps preloaded (similar to what you would get if you rented one from Kenwel or AutoEurope)
I also rented a wifi hotspot from Expresso Wifi for our time in Italy

My experience though I packed the Tom Tom and had it in the car the entire time, I never once used it!
It seemed like 1999 technology compared to using the Waze app on my IPhone since we had unlimited data and Waze (my favorite app at home) was far superior and had visual and verbal notifications for each upcoming speed trap as well as showing speeds you are traveling vs. the speed trap limit.
You would never believe me how frequent speed traps are on the highways and how rarely speed limit physical signs are present. The app if it did not save me money on tickets it most definitely saved me time by being able to speed in sections where there were no speed traps.
While we traveled to some off the beaten path locations where we lost wifi /cell service as long as your intended route had been entered when you left a more populated area the app keeps the map and directions active using what it downloaded previously and your phone's GPS, so we never lost routing anywhere in the country.

Just my $.02 but I left the Tom Tom behind in the car in Venice when we dropped it off, after this experience I would never use a stand alone GPS unit again and no reason for it to count toward weight and space in our return luggage.

Though I fully agree you need something, my preference for Italy would be in order: 1.) Waze app on your phone as long as you have data in Italy, 2.) Car's internal navigation if you are lucky enough to get a car with this and an LCD screen (not happening on an economy or compact rental), 3.) Standalone GPS unit

Thank you everyone for some great advice.

We will be flying into Rome and plan to take the train to Camucia/Cortona where we have rented an apartment for two weeks. We are not buying train tickets in advance and hope to purchase these at the airport. I have read a number of posts stating that this is the best option as one never knows about flight times of arrival. We should be arriving in Rome in the morning from Toronto, Ontario.

Yes my husband will be acquiring an International Drivers license. We hope to rent a smaller type car and a manual transmission. Fortunately my husband can drive a manual although he hasn't for years. hmmmm. But the first week we will get the lay of the land and probably go on a guided day trip or two.

I do have an IPhone. I don't plan on purchasing or using data (I don't think). Will just link up to hot spots? Hopefully our apartment will have fairly good WiFi. We are purchasing R.S. guidebook to Florence and Tuscany. I love R.S. insights and advice. We used his books for visiting Rome a couple of years ago. It was worth its weight in gold !! LOL. We learned many things and took advantage of his many hints and tips as well as being on a cruise message board somewhat like this one where people offered invaluable advice. Thanks again for all your help.

I wouldn't rely only on printed maps and lay of the land for driving around Italy.
You really should plan on some sort of GPS solution.

My post about the Waze app along with the Expresso hotspot rental is because the hotspot rental is probably similar in cost to a GPS rental and for me much more valuable so something folks should look into and compare vs. renting a GPS or buying Europe maps for their GPS.

Just to clarify, an International Drivers Permit is a translation of your state license, so you need both to drive in Italy; don't leave the state license at home!

Have a great trip.