Cortina d’Ampezzo to Bellagio

For #1 yes,

For #2 check whomever you're renting your car from if they have the availability of a one way rental ending in Como.

You could drive a Hertz rental [originating in Venice] from Cortina d’Ampezzo to Lecco or Como [about 5 hours] and from there a bus or taxi [simpler] to Bellagio. We use Autoeurope, for which we have a toll free number to call.

These are a lot of stops. You should plan on at least 3 nights in each location [3 nights =2 full days].

Regarding Tuscany, you can pick up an Avis car leaving Florence, return it in Chiusi and take a train to Rome.

https://www.wanderingitaly.com/maps/valdorcia.html

Thank you both for these replies. I’m also starting to think we have too many stops. Since CT was what lured us to Italy in the first place, I’m considering giving up Milan/Como instead, but was trying to break up hiking (Dolomites) and hiking in CT. Maybe we should just stay in Milan and skip Bellagio or vice versa?

How about this [say 21 nights].

Into MXP, out of Rome FCO.

[3 nights] Bellagio;

[4] Dolmiti [car rental in Como or Lecco];

[3] Venice, dumping the car;

[4] Florence, including a day trip or two;

[3] Tuscany with a car leaving Florence [Val d'Orcia];

[4] Rome [Avis return in Chiusi and a train.

This definitely looks like a more efficient itinerary, thank you!, but CT is very high on our list. We may skip Bellagio and Milan and do this:

Venice (2)
Drive to Cortina (4)
Return to Venice (1), ditch car
CT (4)
Florence (2)
Pienza (3) with car
Rome (3)

Thoughts?

High speed trains do not serve the Cinque Terre, drive from Cortina directly to Liguria and ditch the car in La Spezia.

Train time from Venice to one of the CT villages is 6.5 hours, plus the couple of hours more when changing hotels.

Venice train to Florence [2:13], then a CT village taking the 7:54 from Firenze Campo di Marte [2:29]. Pick up an Avis car in La Spezia for Tuscany, return it to Chiusi [closed Sat afternoon and Sun] and take the train to Rome.

Note that Venice and Florence you have only a single full day.

The only places where the car is totally unnecessary are Venice, Florence, Rome, and also the Cinque Terre.
I would work my itinerary to leave those locations at the beginning and the end of my trip.
From north to south.
Start in Venice.
Rent a car at the end of your Venice stay.
Keep the car for everywhere else. I guess, given your itinerary, you might need to keep it at the CT as well (just keep it parked). Then visit Tuscany.
Return the car in Florence.
Stay in Florence (without car) then take a train to Rome for your last stay.
Alternatively, if you don’t want to backtrack from southern Tuscany to Florence. Keep the car in Florence (parked all the time) then visit Tuscany and return the car in Rome.
If you decide to take this last option, while in Florence find a hotel outside the ancient walls that has parking. I provided a bunch in the post below.
https://community.ricksteves.com/travel-forum/italy/nightlife-in-tuscany

I totally disagree. So driving from Cortina d’Ampezzo to the Cinque Terre? That's what, seven hours? Plus driving in the CT area is ill-advised. Drive 2.5 hours back to Venice and dump the car.

You all have been very helpful! Thank you! Given these inputs along with our strong desire to spend time in CT, we’ve decided to skip the Milan/Lake Como area for this trip. We will also drop the car we need for the Dolomites back off in Venice and travel by train from there. Now, I’m trying to decide how to separate the hiking portions of our trip (Dolomites and CT), which was one of the objectives of Milan. Since the direct train to La Spezia has to go through Florence, I’m considering after Cortina, drop the car and go to Florence and explore the city (2-3 nights), then go to CT from there for our 4 night stay, then return by train to Florence and pick up a car for the Tuscany portion of our trip. Back to Florence to drop the car and train to Rome for the last leg of our stay and our flight back to the US. I know that we’ll be doing tons of walking in each location, but hiking elevation and walking streets and staircases is a bit different, so I’m trying to give us a break between the hiking areas.

Again, thank you for the inputs and the links shared!

Or as another suggested, rent the car in La Spezia to drive to Pienza. I think this is preferred to save time.

If in your shoes, I would take the train from Venice to the Cinque Terre (via Milan is probably easier as it might require fewer train changes than via Florence).

After 5 Terre, I would take the train to Florence. After visiting Florence I'd rent a car in Florence, roam through Tuscany all the way to Rome. Return the car in Rome upon arrival.

An alternative to driving all the way to Rome is to return the car in Chiusi then take the train. This last thing is up to you and dependent on whether you want to visit Orvieto and/or Civita di Bagnoregio along the way. In the latter case, drive to those locations then return the car in Rome.

The best train route Vernice to Monterosso takes 5:27; 26 minutes more for the other villages. The first stop is Florence at 2:13. I say get off there and visit; then later the fast CT train at 2:29 from Campo di Marte. Then a car rental in La Spezia.

Perfect! Thank you!