Driving alone in Italy

Could you share your exact plans with the number of nights at each location?

When you say Milan Airport, is it Malpensa? If so, I'd rather take the train to Milano Centrale then Brescia, and rent a car there, rather than dealing with Milan traffic.

If you arrive at Linate Airport, it's less of a problem.

define navigate! Putting some details into an electronic device that will then talk you through the journey is very different to actually following maps whilst on the move. And does your experience include finding way through towns with ZTLs?

The part of this plan which seems odd to me is what seems to be an intention of flying from Venice to Naples (Ryanair??) in order to tour Puglia. Why not use the train for this part, Venice (either station) to Foggia is possible every hour with a leisurely break at Bologna. If you're not actually planning any time in Venice then take the car to Bologna and catch the train from there.

Only you really know your confidence levels.
I'm a bit older than you, but lived in Spain for 12 years. I had an automatic - and a partner!
I would not have wanted to drive solo anywhere I did not know. In fact, I still wouldn't, even in UK!
Think about train to south Lake Garda and lake steamers for sightseeing there.
Rent a car or train to Bolzano, say - fairly straightforward drive.
The next bit is more diifficult to decide.
Don't know yet why Venice features, but you could fly straight to Bari.
Even the train is over 9 hours.
Rent a car there for local touring.

Many tourists that rent cars in Italy get very expensive tickets in the mail months after arriving home.
Parking is difficult in larger cities and many smaller cities have zones that don't allow entrance unless you live there.
Also, theft from cars is a big issue in places like Naples.

Suggest you consider taking the train or group tours.

Well...I drive alone here all the time, just me and my semi-trusty GPS, but I live here. I just got back from a big loop around central Italy, Abruzzo to Tarquinia on the opposite coast via autostrada, returning via back roads through Lazio, Umbria, and back to Abruzzo. The roads are typically safe in that they are well-paved and well-signed, and drivers have slowed down due to the ubiquitous speed cameras, but of course you can always find an idiot overtaking on blind curves...I think your plan is just fine.

For me, the trickiest driving has been around Milan just because the roads are bigger (six lanes each way sometimes) with lots more traffic than where I usually drive. Also be aware there is one privately-owned toll road up there for which you pay the toll online after driving it. Don't forget to pay if you end up on that road! Pedemontana. The rest of your itinerary is fine to drive and gives you lots of freedom. I would do it and have done it.

One suggestion: if you are here a minimum of 3 weeks, consider the French car lease program instead of a regular rental car. The insurance included is truly comprehensive. It pains me to tell this story, but when we moved here, we leased a minivan on arrival due to bringing too much stuff. I had that car in Switzerland, northern Italy and Abruzzo for 4 months. I returned it without a single undamaged quarter panel - significant dints on all sides, mostly from encounters with Swiss rock walls. They didn't even blink and didn't charge me one nickel extra. short term car leases Europe

If you want to do it, go for it.

You can do this!! I am in your age group, ore or less, and I've driven in southern Italy alone.

If anyone tells you the it is difficult to drive out of Naples airport, disregard them. The autostrada is right by the airport and you'll get on it after exiting. (But you could consider train from Naples to Bari and rent the car at Bari airport)

What makes the driving a delight is to rent a car with a GPS installed;;not the to depend on peering at a tiny phone screen. You can set the voice commands to English, if you prefer.

Yesterday I arranged another rental at the Bari airport, from SIXT. (Will go in a few weeks). I recommend that agency.
I get GPS included and all coverage, including theft, with no deductible.

Use a GPS device/app that you are familiar with. In Umbria and Tuscany I used my brought-from-home Garmin and got routed onto a dirt road and a back country road that was two-way but without room for opposing cars to pass each other most of the way (luckily I didn't encounter another car). So I started using google maps on my phone as well and sometimes got conflicting directions. At home and in the US I use Waze all the time now (didn't have access to it on that Italy trip). The problems with Waze are it is a battery hog (not a problem if you bring a charging cable) and also a data hog.

I think that there is way more to driving in Italy than you may expect.. Americans drive in linear patterns. Most Italians do not unless on a motorway. They are spatial and assume that a space will miraculously open up if they decide it should so they just go where they want. One hand for the steering wheel and one for the horn. Add in people on motor bikes zipping around you on both the right and left.

You mention exploring small towns. This means narrow roads and often extremely limited parking.

I don’t think you would find this a positive experience!!!!

Picking up rental car at Milan Airport driving from milan to lake
garda

If you are arriving on a transatlantic/overnight flight this is probably not a good plan. It's at least a 2 hour drive. I would only consider this if we had a driver and a navigator.

Train to Garda then on to Bolzano- pick up car there would be a safer plan.

One of my favorite things about traveling in Europe is riding the trains. It’s relaxing, and there is beautiful scenery, and people watching on the train. Your itinerary is easily accomplished by train travel, without the stress of finding parking, fuel, directions, and safety, among other concerns.