Help re Itinerary - especially in Tuscany area

Florence is in Tuscany but I understand what you're asking.

It really depends on what you want to see and do in Florence as well as the rest of Tuscany. If you can do Florence as a day trip then it might make more sense to stay somewhere else. If you want to spend several days there it might make more sense to do day trips from there. With only 5 nights I would choose a single location and do day trips. I wouldn't rent a car until getting to Florence and then only if the towns you want to visit don't have good bus or train connections. Parking is expensive and you won't be able to drive into any of the cities you plan to visit including Florence.

I would drop the car off in Florence before heading south.

donna

I know I'm making it more difficult than it has to be....

Venice is 3 nights!
Tuscany 4 nights
Amalfi 4 nights
Rome 4 nights

where should I spend the other one or two nights? Umbria?

Do you think it is a mistake to not stay in Florence? (I personally find it very crowded, but my friends have never been there?)

Do Florence at least as a daytrip. There are many other great hill towns: Siena, Montalcino, Lucca, Arezzo...

If you want to stay in Umbria, and you have a car, I like Todi, Gubbio, Assisi or Spello. Gubbio is a bit more out of the way. But frankly I think you have enough places without it. Save it for another trip, to me it is even more beautiful than Tuscany - the landscape is a little more rugged.

If you want to stay on the Amalfi Coast, I prefer Praiano to Positano. Less crowded. I know a small hotel on the water with free parking. Praiano is between Positano and Amalfi, so you can go in either direction and miss half the traffic.

By the way, the island of Torcello while you are in Venice would be a worthwhile excursion, and it's not far from Burano.

so I have 16 nights total....

venice 3
Tuscany/Florence 4
amalfi 4
rome 4

where should I put the other night?

With 4 people to fill up the car, driving can make sense and facilitates the stop at Maranello/Ferrari, but having a car that early in the trip also points toward sleeping outside of Florence, not in the city.

Yes, I would stay in Umbria for one night on the way to the Amalfi Coast. I love Orvieto. It's easy access off of the Autostrada and is a lovely hilltown. Has a beautiful Duomo, wonderful restaurants and, of course, Orvieto Vino.

Have you looked at the driving times involved. A drive from Florence to the AC will take about 5.5 hours without traffic. From Venice to Florence is about 4 hours and from the AC to Rome is about 4 hours. That's a lot of time for 4 adults to spend in the car. This will take up at least half a day when you change locations.

Donna

3 nites Venice. Pick up rental car @ Station. 5 nites Tuscan countryside. Drive to Orvieto.

Drop car by station. Direct train. 3H19m. Orvieto-Naples. Circumvesuvian-Sorrento. 4 nites
Sorrento makes a good transportation base for this area. Train Naples-Rome 4 nites
For Tuscany lodging, this, http://www.collelungo.com/EN/appartamenti.html , is very centrally
located.
With a car you are able to go where you wish when you wish.
From Venice to Modena is 120 mi. Modena-Castellina 110 mi. There are tolls along this route.