$600 is very good. I was curious and just checked hertz.de and they quoted about $850 in mid-February for two weeks, but the smallest car they had, manual. It did have snow tires. Of that $850, $450 was the drop fee, so it does include it online on that website. $400 for 2 weeks rental isn't bad, but of course, that's a teeny car. The SUV was more like $1030, but same drop fee.

http://www.autostrade.it/autostrade-gis/percorso.do#

That's the official Italian autostrade site. You can use it to figure out tolls. Italian tolls aren't that bad but fuel isn't cheap. At the moment diesel is over €1.3 at selfserve. Gasoline is far more expensive even before you factor in the worse mpg.

This site will tell you how much time, and how much money, each leg of your trip will require:

https://www.viamichelin.com/

I would suggest dropping off the car before arriving in Venice, or upon your arrival. The drive between Venice, Bologna, and Florence is not interesting. It's all autostrada, with heavy truck traffic and lots of tunnels (going through the Apennine mountain chain). After your visit to Florence, you could pick up another car for your time in the Tuscan countryside, and you could drive that car to Rome. There are some scenic backroads to Rome, so it's not such a bore as the drive from Venice to Florence.

While in Rome, the car would be an expensive nuisance, so I would drop it off on arrival.

In all of the cities you plan to visit, make sure you know all the rules regarding limited traffic zones, bus lanes, and other traffic issues. The large European cities were not designed for motor vehicles, and most cities do everything in their power to discourage people from bringing them into the city center. The traffic laws are enforced with hidden cameras, and it's very easy to rack up big fines without realizing you are doing so. What happens, at least as regards Italy, is that six months later, you get a letter notifying you of a traffic violation, for which the car rental agency has charged your credit card for their services to the traffic police in helping them find out where you live. The actual ticket will follow, usually months later.

But he has time to take side roads between Venice and Florence - like via Mantua - I once biked Venice-Bologna-Florence on nice side roads and negates hassle of returning car and renting another one. Stay in a hotel outside the no-go zone in Florence and use public transport - buses and trams to get into the center.

He's coming St. Nick's day. It'll be dark in the morning and dark in the afternoon. Staying in the cities is far more interesting then commuting.

Not talking about commuting from other places but just outside the no-go for auto zones - like in Florence outside the ring road - can walk in even as I did from a B&B on north side of Florence. In Florence in a real neighborhood with all amenities but no not from other cities. Or just stop in Florence on a Sunday when the ZTL is not in effect.

https://www.visitflorence.com/touris...-ztl-zone.html

Or if only wanting to see Florence for a day then yes base in Tuscany and take train or bus in and back - just seems two separate car rentals cumbersome and could be more expensive?

Or go to Tuscany from Venice and when done return car in Florence and then train to Rome?

Not sure Tuscany much fun if snows however at higher altitudes than Florence.

Pre-planning a road trip to/though these cities in December isn't all that practical. Sorry -- even if you are from the upper midwest. The days will be extremely short, so you won't have a lot of meandering time. But it is your trip.

If you just really REALLY want to experience winter driving, take trains and then rent a car for a few days to explore the countryside. Then drop the car and move on. And you will save the one way drop off fee so you can rent 2 or 3 different cars for a few days each and still save money.

Just getting a car in to some of those cities will be a hassle.

Yes even to stay in a hotel inside the ZTL in say Florence you can drive to it to dump bags and stuff but have to right away drive out of it and park in a remote lot - leave nothing of value in any foreign plated or rental car.

Tim330i--

We did drive between Prague and Vienna because my dad is a senior citizen and we wanted to see the towns where his family was from along the way. We got the car at the Prague Airport right after our flight. Driving to the small towns in southern Czech was pretty easy.Two places along the way worth a stop for you would be Lednice and Mikulov. Google them and let me know if questions...

Finding a reasonably priced hotel with parking was a pain in Vienna. Of course, we went in the fall and on a weekend. We ended up staying somewhat outside of the main part of the city.

If you are also struggling for lodgings on this leg, you could also stay at the Enziana. Decor was not great, but it was clean and decent bedding, newer bathrooms. Main advantage of the Enziana that you can take this little trolley train into the city core. It goes right by the hotel. Staff is also very friendly and almost always someone is on duty who is fluent in English. You do need to let them know upon booking that you will need a parking spot. And it's a little weird upon arrival because you park behind the hotel--do some mapping of this ahead of the time. That trolley goes by in front so don't drive along there.

http://www.enziana.at

When we got back to Prague, we had no need for the car. We dropped of my dad at our new lodgings and drove the car to the airport and turned it in. This allowed us to get a very central apartment with more bedrooms and privacy. However, even stopping to check in at the lodgings, the police came up and told us we had to move the car within 10 minutes or it would be towed. That is the norm in the old city centers and why a taxi, Uber or mass transit is easier to get around.

Had we wanted to stay at that lodging and keep the car, there was just no lot or structure anywhere nearby to pay and park it. Also the driving on cobblestones was pretty nasty.

So if hitting the rock-bottom prices is not your concern, I would go with a mix of driving and trains.

Good luck!