1st trip to Italy: Rome to Florence and Tuscany in between

I missed it was fall--you may want to share the specific time frame. Cinque Terre can get pretty rainy in late October.
I like this order better, but you don't have to go all the way to Florence to pick up a car. Many smaller towns have rental agency offices, and there is no fee for dropping off in a different location within the same country. I'd do an exhaustive search of rental options. Lucca or La Spezia maybe?
Be sure you know about ZTL.

I wish I could take back the 3 nights we spent in Monterosso. If it wasn't for Rue Cler, the Cinque Terre would be the biggest disappointment I have experienced in all of my trips to Europe. Add those nights to Tuscany, Rome or Florence.

One suggestion after five trips to the Chianti region and surrounding areas is to stay in a Chianti village instead of San Gimignano which mobs of tourists, bus tours. . Visit San Gimignano as a day trip. Stay in Siena, Radda, Castellina, Panzano, Greve or others along historic SR 222, the Chiantigiana connecting Siena and Florence.

Train to Lucca (~1.5-2 hours), Lucca 1 night Train to Florence , P/u
car and drive to San Gimignano, (60 mins). SG 5 nights, Tuscany base:
Day trips: Montepulciano, Siena, Chianti, Visit: wineries, biking
culinary classes, etc. Drive to Florence, drop luggage at Hotel, drop
car at airport or other location.

There is no need to go into Florence just to pick up a car. There are several rental agencies in Lucca- Avis, Hertz, Europcar...) We dropped at the Avis office in Lucca this past spring.

No need to go IN to Florence to drop your luggage either- just drop the car at whichever return location you have chosen then go to hotel in Florence. Take a taxi or tram, the agency desk will call a taxi for you if needed. Then you don't have to worry about ZTLs, parking etc. IOW- you do not want to drive IN Florence at all.
Be sure to check open/closed days/hours at the rental agencies.
There are several threads on the forum on how/where to drop in Florence that include Roberto's directions.

We always use AutoEurope.com for car rentals. Be sure you do your homework on driving in Italy, all drivers must have an IDP.

As for itinerary
Rome needs more than 3 nights- which is only 2.5 days to sightsee. Your first day is a jet lagged blur. Add at least 1 night to Rome
I'd skip CT for all the reasons above- time of year, crowds, etc.
Give Lucca 2 nights. With only 1 night you won't be able to see/do much at all, not worth it for a 1 night stay IMO.

Alternatively- if you drop CT
15 nights-
Rome 4 nights
Train to Orvieto- 1 or 2 nights- lovely town- pick up car here at the Hertz.
Drive to your location in Tuscany 5 nights
Drive to Lucca 1- 2 nights- drop car
Train to Florence- 3 nights

I think Christine’s advice to drop the CT and add days to Rome and Lucca or Florence is excellent. Orvieto is a gem, not to be missed. I also recommend AutoEurope for car rentals.

Unless you’re hiking in the Cinque Terre give it two nights and add a night to Rome. I agree with valadelphia about renting a car in Lucca. I also agree with Suki about making San Gimignano a day trip; San Gimignano is worth a half day.

I rented from Europcar in March at the Florence airport. There was a drop-off charge of €80-100 for any other location. Driving in Tuscany has its challenges - winding, hilly roads that are often 2-lanes without shoulders and poor signage or none at all. I used a Garmin and Google maps and sometimes got conflicting directions (like at a T-intersection one said right, the other left). Virtually all towns with historic centers have ZTL's (only authorized vehicles) and if you enter inadvertently, expect a large fine €€€ for every violation. Hill towns have parking lots outside (and below) the walls. Some are free, many are paid by machine, some when you enter, some when you leave. Then you climb up to the town. In late March with things just reopening after Covid, I always found parking. In October it may be more difficult.

Since you’ve never driven in Italy, download (yellow banner at bottom of page) the driving in Italy book. There a alot of different rules and regulations that are not found elsewhere in Europe.

https://italybeyondtheobvious.com/

Christine has given you a great itinerary.
I agree with Suki as to the crowds in San Gimignano, they can be overpowering.
Her suggestions of other Chianti towns is spot on.

Chiani recommendation of an alternate way to plot your course cannot be overstated.

Have a great trip!

You should pick up the car in Lucca and return it in Florence BEFORE GOING TO THE HOTEL to drop your luggage. Unless you stay away from the city center you may not be able to drive to your hotel.
I don’t know when you are going in the Fall, but if it rains the Cinque Terre won’t be a great place to visit. I would increase my nights in Lucca and visit the Cinque Terre on a day trip from Lucca (if weather permits).

I like many of the replies you’ve been given. My string advice us PACK LIGHT! Maybe 2 pr of shoes and leave out heavy items. No soap/shampoo etc. it’s easy to use washer at lodging half way through, hang to dry. Enjoy!

thanks all for the great feedback. got a Hertz rental in Rome with drop at La Spezia. much easier. Cheers, Fred