Does this look ok? Too much driving?
Fly into Milan and stay three nights (attend opera at La Scala)
Drive to Lake Maggire area and stay one night
Drive to Santa Magherita and stay one night
Drive to Lucca and stay one night
Drive through Chianti area and stay somewhere
Drive to Assisi and stay one night
Train to Florence and stay two nights
Trian to Rome and stay four nights. Fly home

You should post in the Europe forum

I would say, yes, too much.

I would say, yes, too much driving.

Actually, it's not necessarily the driving that's too much, but the moving around, checking in & out of hotels that's too much. You burn a lot of time doing that. I much prefer to stay one place more centrally located for a few days and drive or train for day trips.

Don't carry too much luggage, it's a hassle getting it on and off the trains, I remember dragging it up the step to the train from the platform on the Florence to Rome train.

I wouldn't stay anywhere for 1 night, barely pays to check in and check out.

Too bad you don't have Venice on your itinerary. For a first trip I would do Rome, Florence & Venice.

I'd save Milan, Tuscany and the Lakes for my second trip.

We spent 8 nights in Rome and barely scratched the surface.

I see you have 14 nights, I'd do 6 nights in Rome and the outskirts, 4 nights Florence and 4 nights Venice. You can do it all by train if you prefer. Just one man's opinion.

What ever you decide, have great trip.

I would absolutely hate having to drive almost every single day of a trip. All those "stay one night" would make me nuts.

You say 1st time to Italy, but have you traveled before? To other places in Europe or abroard? Or this is your first time ever out of the country?

I ask only because some people do like to have an intensely fast-paced trip. But I'm not one of them. I would cut at least half the places you mention. Actually if it were me I wouldn't rent a car and would go by train from Venice, to Florence, to Rome, and skip the rest.

Forget one niters--this is not the Amazing Race.
Do you have tickets for La Scala?

I see 5 hotels for this trip---max.
Stresa
SML
Tuscany
Florence
Rome

When is this trip? Some of your destinations only make sense when the weather is nice.

I don't have a problem with road trips in Italy. I enjoy them. But I think you can do see Lago Maggiore as a day trip by train from Milano (and only go if the weather is nice), and then take a train to Santa Margherita Ligure.

You can pick up a car in Rapallo (it is literally 4 minutes away from Santa Margherita Ligure) and drive to Lucca for lunch and a look-see. I would go to Chianti from there without spending the night in Lucca.

If you haven't already bought your plane tickets, I would switch your departure airport to Florence. That way, you could drive from Chianti to Assisi, spend the night, and the next day drop off the car in Orvieto (in Umbria) and take the train into Rome. Then make Florence your last stop and fly home.

If you already have your plane tix, some people see Assisi as a day trip from Florence, so you could consider that instead of an overnight in Florence. But howevermuch it drives other people crazy you are doing a road trip, if it isn't bothering you, then what the heck. It's your trip. Decide for yourself.

But if you can take trains instead of drive to some destinations, it can make for nice variety.

By the way, I don't think you can drop off your car in Assisi, which is what your first post implies you want to do. If you need to go to Florence ahead of Rome but don't want to drive a car into Florence, the simplest thing to do is drop off the car at the Florence airport and take the shuttle bus into Florence, or a taxi.

Just so you know the drive times:

Santa Margherita Ligure > Lucca: 90 minutes

Lucca > Bucine (east of Chianti): 90 minutes

Bucine > Assisi: 1.45 hrs

Assisi > Florence: 2 hrs.

Another reason I suggest the train to Santa Margherita Ligure is that the drive isn't any fun. Something else you might consider that would save you some time is to take a train from Milan to La Spezia, and stay a night in a scenic town near there -- Portovenere, le Cinque Terre, or Levanto if you need a flat town -- before returning to La Spezia to pick up a car and driving it to Lucca. You would have a very short drive to Lucca. (60 mins.)

You could consolidate your hotel stays a bit by either making Lucca a day trip by train from Florence, or vice-versa.

One night hotel stays are a major PIA. I would figure out how to do some of these visits as day trips from a place you are already staying and not change hotels so many times.

Thanks everyone! We are going to lessen hotel stays and do more day trips.

Chism