Driving in Tuscany

It would be helpful if you could tell us exactly where you are staying in Chianti, what you want to see, how long do you have, where are you traveling from, leaving from, etc. There are many very helpful folks here, but they need a bit more information.

The Chianti area is a hilly rural wine producing area between Florence and Siena, much like Sonoma county and Napa Valley in California.

Although there are buses serving the small towns in the area, they are infrequent, and are there mostly to serve commuters and school goers to Florence and Siena, therefore they are a viable option only at commute time. The bus service is scant to non existent in the evenings and all day on Sunday.

My suggestion is to rent a car.

If you decide to rent a car, there are a couple of things to keep in mind......

• each driver on the rental form will require the compulsory International Driver's Permit, which is used in conjunction with your home D.L. You can obtain an IDP at any AAA office for a small charge.
• you'll have to be extremely vigilant to avoid the ZTL (limited traffic) areas which exist in many towns in Italy. There are hefty fines for each pass through these. Do not drive into Florence! Be sure to do some homework on what the ZTL signs look like.

We are flying into Rome and take the train to Naples and then off to Sorrento for 4 nights. Our plan is to take the train to Florence and then either rent a car or take a bus to San Casciano in Val di Pesa for 4 nights. We plan to take a couple of day trips to Florence and Sienna. Take the bus or train to Florence and then the thought was to maybe rent a car to go to Sienna and other hill top towns. Then we are going to head to Lucca for a few nights. I would like to get to Cinque Terre as early as possible to make a day trip out of it and then drive back to Lucca or take the bus back depending on the latest schedule. Would love to explore the area with the Devil's Bridge. Then off to Rome, if we had a car then we would return it, for 2 nights.

Are your accommodations in the town of San Casciano or nearby?
If it’s a villa/Agriturismo outside of town, you need a car.
A bus can work IF:
1. Your accommodations are in the center of town.
2. Your day trips are to Florence and Siena only.

However be aware that bus service ends early in the evenings, so you can’t stay in Florence (or even worse in Siena) past 8:40pm (that is when the last bus to San Casciano departs from Florence.

If you intend to visit the Chianti countryside or smaller towns, a car is recommended.

Actually if this were my trip, I would probably rent the car in Sorrento and drive directly to San Casciano. If you don’t mind the long freeway drive (about 6 hours), the price of driving would be cheaper than 3 train tickets. It’s up to you. The trains+bus would take about the same time, but of course someone else would do the driving.

Regardless of whether you rent the car in Florence or Sorrento, if after San Casciano you are headed to Lucca for a few nights, I would return the car in Lucca. You can then comfortably take the train from Lucca to the Cinque Terre.

4 nights is three days. You'll need a car in Chianti.

You need to do some serious trimming of your expectations. You're trying to do too much in not enough time.

You also don't mention when you'll be there. Things will take a lot longer during peak season compared to shoulder or off season.

Lay out your plans in a detailed list, day by day. Also look at travel time from one place to another. Lots of folks forget to factor in how much time it takes to move from one place to another.

Chianti is charming. You'll have to decide what kind of experience you want to have - drive by and wave or savor the areas you'll be visiting.

One of the pleasures of independent travel vs tour travel is you can plan in time to act on a whim. When we visited Tuscany on a 10 day trip, we were locked in to activities on one day. We had a wish list, but we had the freedom to make changes. We did a few things not on our list, but discovered when we got there. If at all possible, pencil in a "free day" to allow for serendipity.

Yep. Car. And read this: https://www.italybeyondtheobvious.com/dont-mess-with-ztl-zones