My husband and I are traveling to Rome mid-May 2026. My current itinerary is as follows:

Rome: 2 nights
Levanto: 2 nights
Travel to Florence: 2 nights
Reggallo: 5 nights
Milan: 1 night

We land in Rome and will stay 2 nights. I have been before, hence the shorter stay. From there we have reservations in Levanto for 2 nights and hope to visit Cinque Terre. We do not have reservations yet for the two nights after Levanto. Could stay somewhere enroute to Florence? Looking for recommendations. The longer stay in Reggallo is for a course I am taking. Any information on what to see or do around this area would be greatly appreciated. We will make our way to Milan to fly home and only have the night prior to our flight.

Any input about the above itinerary would be greatly appreciated but specifically what to do about transportation. We thought about trying to use the train throughout but fear it might limit us especially around Cinque Terre. The property in Levanto has parking. Would it be recommended to get a car the day we leave Rome that we would keep the remainder of the trip and drop off in Milan at the end of our journey? Thank you in advance for any and all input and recommendations.

So you land in Rome. The next day you spend better part of six hours on a multiple trains for Levanto. Spend a day. Next day almost three hours to Florence

Then to end off you spend three hours getting to Milan for your flight home

You don't want a car for the vast majority of that trip. Having parking for part of it just means you can watch your car sitting . You won't need it in Florence.

My suggestion either add more time so you don't have two days here and there. Or drop places like Cinque Terre that are hard to get to.

Rome to Florence by train is ninety minutes. Ninety very easy minutes. But it's your trip and you need to decide how you want to spend your time. If Cinque Terre is important maybe drop Florence if you can't add more time

Can't address your specifics, but to me even if you hire a private car or taxi for some excursions and off the grid trips you are better off than renting a car. If the train gets you largely where you want to be, stay a few days wherever, relax and do day trips by rail and hire a driver. The hassle of pick up/return, fuel, maps, parking, speeding tickets, insurance....what are you really saving? You may save $$ and still see and do everything you want and let someone else drive. My thoughts.

Reggallo? Never heard about!

You've been to Rome, but have you been to Florence? If not, two nights is barely worth the effort. Florence is small geographically but enormous in terms of treasures and sights. And with so many easy day-trip options from Florence using public transportation, 5-6 nights there would not be too much.

As Reggello does not have train service, you will want a car if you hope to see anything outside of the town. You could pick up a car in Florence as you're leaving or in Arezzo, a very nice town about an hour by train from Florence. FYI, Arezzo holds a great antiques market on the first Sunday of the month and the preceding Saturday. Unless you have something specific you want to do/see in Milan, I'd change the return flight to FCO. Malpensa is a lot farther from Reggello, and most likely you'd drive the boring autostrada the entire way (4.5-5 hours). In that amount of time, you could drive mostly secondary and more interesting/scenic roads to FCO..

From Reggello, I'd explore Chianti and drive as much of SR222 (Chiantigiana) as possible.

If you keep the CT in the itinerary, you don't want or need a car.