This is not a trip report.

FWIW, I'd try to get the car in Bellagio as I suspect the drive along Lake Como is fantastic. With five people, economy-wise I think the car would work better

If Bellagio don't have the right car pcik up consider that Como is just sa short bus or boat ride away - a large commercial town with lots of car rentals.

Arranging cars ahead of time thru U S middleman is usually gthe best deal rather than renting directly in Europe. so contact Kemwell, Auto Europe, Hertz, AVIS and other U S rental companies about their European offerings and where you can pick up your car.

Thanks. We are coming from South Africa, so i will then probably have to just book online, although i will find out from our rental companies if they have such connections.I have heard so much about the awful traffic congestion in Italy though. Will this be a problem for us?

IF you DO get the car in Bellagio I suggest you look at exactly where Bellagio is located on a map. It is not exactly in a great location for driving elsewhere, especially to Pisa, etc. You might be better off taking the car ferry over to either Varenna or to Menaggio to drive from one of those locations since they are more ideally located for driving elsewhere.

Now, as to scenery along the lake, you can see some of that if you take the train to a place like Lecco and rent a car there. As an alternative you could take one of the ferries all the way to the city of Como and drive from there.

Will this be a problem for us?>

Not so much driving around rural Tuscany as it will be in large cities like Florence where having a car is a liability as it cannot be driven in the city cenre,parking can be hard to find and expensive when it is - many hotels may not offer parking, etc.

So if going to big cities leave them to the last and turn in your car in say Florence and take the train to Rome or Venice.

Go to Google Images and enter ZTL. You will see what the signs look like for the car free zones look like. It may cost you hundreds of dollars if you pass these signs. I got lucky. It only cost me abot $120 USD in Vicenza. Someone recently reported a couple of hundred in Florence.

Then google "ZTL Florence" or any other city you might want to visit. It will show you the actual limits of the ztl's in that city on a map.

I am afraid you cannot really rent a car in Bellagio as it is a tiny village with limited service; I understand there is a garage there, but you would likely have to bring back the car to Bellagio.
IMHO the easiest thing to do is ferry to Varenna, train to Milan, fast train to Florence, and then rent the car in Florence. It is going to be a long day, and you should better have light luggage, but this is the quickest solution as train between Milan and Florence is much faster than driving.

Thanks asps. If we ferried to como and then rented the car there and drove the rest of the way to San Gimi, do you think it would still be better for us to catch the train? And if we went the train route, would it be better to go from Milan to Florence, or Milan to Pisa and then hire the car?
Thanks so much for all the acvice. Much appreciated.

I would just say drive the whole way from Como - it is not that long via Autostrada. If train Pisa is a lot more driveable to get out of that Florence would be. If the case of Florence consider taking a train to Florence' Rifredi train station, a main station a few miles north of Florence's main in town station that could be a complete hassle to drive out of for a novice at least.

Or try Empoli, a fair-sized town with a main train station that is closer to San Gimi than either Pisa or Florence I beliewe.

On further review, I think your best option would be to take the train to Pisa if it's only around 4 to 5 hours or perhaps to Empoli. The traffic around Milano and then to either Pisa via Genova or San Gimi via Florence is going to be pretty bad.