Tuscany and Sorrento - Transportation Questions

We plan to use Arezzo as a base for exploring Tuscany by car. This seems very doable, but please chime in if you think otherwise.

It works, certainly, but it could be a fair bit of driving depending on where you’re going. Arezzo is on the eastern edge of Tuscany - Montalcino and Siena are over an hour away and Montepulciano is about an hour. For some that’s no big deal, others may find those drives on the longer side of desirable. Assuming you’re only renting 1 car for the 5 of you, it will likely be crowded.

The advantages of course are not repacking and moving hotels, and if you’re staying near town, the ability to walk to shops and restaurants

Agree with 1 on 1--it all comes down to the details. I decide how much driving I want to do and find a central accommodation. A small SUV would probably fit you all.
As for the transfer, it's not going to break the bank on a trip like this to make your life easier.

We enjoy driving, getting lost, and finding our way back home somehow. An hour in the car is nothing for us.

The train from Naples to Sorrento isn't that bad, but you'll have 2 or 3 flights of steps to get to the Circumvesuviana platform to Sorrento after you arrive at Napoli Centrale. But cost is only about €15 for the 5 of you. Travel time from train station to train station is 70 minutes. There is a train every half hour or so.

Private car for 5 will likely be about €200 and drive time will be about an hour. Less stressful except for the person in the front seat watching the driver zip through Naples traffic. Depending on where your hotel is in Sorrento, they may be able to get you all the way to the front door, or at least close.

*if you choose the train option and your hotel is too far to walk with luggage, be warned that a taxi from the train station won't be cheap. We were about a 5 minute walk from the station in April, but it was raining and the taxi cost us €24. For 5 people you'll likely need 2 taxis.

There are plenty of places to see close to Arezzo. I would not skip over them to go farther places, but of course one or two longer drives would not be unpleasant to those who like long drives. If everything on your dream list was farther away, I'd have a think.

1. It depends on what Tuscan locations you want to explore. Besides Arezzo itself, from Arezzo you can reach in less than one hour the following popular tourist destination towns: Cortona, Lucignano, Monte San Savino Anghiari, Poppi and the Casentino Valley, Castiglion del Lago, Loro Ciuffenna. If you have other locations in mind, then it might take longer than one hour to drive there. So tell us which you are interested in and we might indicate a closer base.

2. If you have a rental car, why don't you drive there? I know it's 5 hours' drive (nearly all on 4 to 6 lane freeways), but with 5 people, it might be less hassle (and less money) than multiple trains plus a private transfer. You can return the car at Sorrento if you don't need it (or want it) after you arrive in Sorrento.

There is an escalator in the Naples Centrale station to the Circumvesuviana level (and a long walk), and an elevator in Sorrento.

I'm thinking I will rent and return the car in Florence with the plan of driving to/from Arezzo. I need to research the other posts about how best to rent in Florence....

Thanks for the feedback on Arezzo. I decided to change our lodging to something more central, so now we are a little bit outside Siena.