Train vs Car -- Monterossa al Mare to Florence

If you rent a car read all you can about ZTL zone laws so you don’t incur hefty fines that will arrive in the mail six months later: https://it.usembassy.gov/u-s-citizen-services/local-resources-of-u-s-citizens/transportation-driving/.
The city of Florence is loaded with ZTL zones and is no place to drive a car. Especially since there’s a nonstop bus from Florence to Siena that drops you off outside of Siena’s old town (1h). Take that instead and rent your vehicle in Siena.
Trains are a hassle when there’s a transfer so pack light and do laundry instead.

I cannot comment on the train, but if you are comfortable driving at home, you will not find driving a challenge in Italy. They drive fast, but if on the Autostrada, stay in the slow lane. If on secondary roads, expect to pass and be passed.

We drove to the edge of Florence without difficulty. I did not drive in Florence. I would not drive in most major Italian cities due to driving restrictions and parking. So it depends on the location of your hotel. Florence is easy to walk. Perhaps stay in a town near Florence and train into town.

In Sienna, we have parked outside the town near an escalator for free. Assisi was more challenging, but there is parking at the edge of town.

Enjoy your trip.

I believe the nearest auto rental to Monterosso would be La Spezia - you would have to take the train that far and schlep luggage anyway. If you get the rail itinerary with one connection, the worst you would have to do is to change platforms - going down below the tracks and crossing over to the second platform. There is often an elevator available for changing levels.

And then what do you intend to do with the car once you reach Florence, where it would be a liability?

No. You shouldn't rent a car in La Spezia (near Monterosso) because what are you going to do with the car while in Florence? It will have to stay parked the whole time because the entire city center of Florence is closed to non residents' cars. Basically you will be wasting car rental money plus parking fees (at 25€ a day or more) for whatever number of days you are in Florence.

You should bite the bullet and take the train from Monterosso to Florence. Many train solutions require only one change (mostly at La Spezia or Pisa), with 3 solutions (2 in the morning and one in the evening) even fast with the Freccia high speed train that in about 90 min goes from La Spezia to Firenze Campo di Marte station rather than Firenze Santa Maria Novella.

Any Florence station will work, since, with luggage, you will still to take a taxi from whichever station of Florence to the hotel.

Train info here:
www.trenitalia.com
Station names are in Italian. Enter from Monterosso to FIRENZE (TUTTE LE STAZIONI), i.e. Florence all stations. There are at least 15 solutions a day requiring only one train change, and just as many requiring 2 train changes.

Leave the rental car to when you depart from Florence to visit the Siena area.

Thank you all for your responses. You've convinced me to stick with the original plan and wait until we leave Florence to rent the car. We hope to rent the car on the outskirts of Florence so we don't have to deal with the city driving. If you are aware of rental agencies on the outskirts heading towards Siena that you could share with us that would be great. Thanks again for your feedback!!

It’s either downtown near the station or the airport, tertium non datur.

I would definitely suggest taking the train from Monterosso to Florence. It's a very easy trip and you'll be able to relax and enjoy the scenery along the way.

As the others have mentioned, a few caveats to be aware of with car rentals.....

• You'll need to be vigilant to avoid the ZTL (limited traffic) zones that exist on many Italian cities (not just Florence). Each pass through one will result in hefty fines!
• Each driver will require the compulsory International Driver's Permit, which is used in conjunction with your home D.L.
• You'll also have to watch your speed carefully, as there are automated speed cameras.

Thank you so much again for your feedback. Getting the International Driving Permit is on my "to-do" list prior to our trip (we obtained them previously for trips to Portugal and France). And I will definitely read up more on the restricted zones before we leave. Hoping to get our rental car as much on the very outskirts of Florence as possible so that we avoid driving in the city. In Siena we have accommodations that include parking and our trip to Assisi will probably be a day trip only, so we will most likely park outside the town. Thank you for the links you've given me. Appreciate you all!