Driving from Pienza to Sorrento

I would just drive. It is not a very interesting drive and it takes a solid 5 hours, but it is an easy drive.
Driving to Orvieto, taking a first and possibly a second train to Naples, then the Circumvesuviana to Sorrento, will be less fluid.

Drive! From Pienza drive the two lane highway to Chiusi-Chianciano freeway entrance, then take the freeway south (Roma direction) all the way past Naples. There is nothing frustrating unless you get frustrated when you drive on an interstate freeway in America. There are numerous rest stops (Area di Servizio) on the freeway where you can eat, shop, use the restrooms, refuel without needing to exit the freeway.

Googlemaps looks like route avoids Rome and Naples traffic. I am hoping that the traffic into Sorrento for car drop off would not be too difficult in non-peak season (October mid week).

Italian A-something divided freeways do not enter the cities; you won't take Rome's ring road either.

October or not, memorise the ZTL sign.

Driving route on viamichelin. Return the car to Hertz on Via Capo,8. There is cab stand nearby.

I would not assume that the drive is faster, especially if you book Frecciarossa trains. Driving a car in Sorrento is not as bad as in Naples but still annoying. If you demand control of your personal transportation, sure, take the car. I would take the train.

I will say that the last segment, Naples-Sorrento on the Circumvesuviana train in high season is not for everyone. It's like the worst subway anywhere, no A/C, jammed seating. Fair disclosure. We were happy to pay for a car service back from our five nights in Sorrento to the Naples train station, also because we were overcharged for a taxi from the Circumvesuviana to our downtown Sorrento hotel on arrival.

From Chiusi to Sorrento is nearly 4.5 hours' drive, to which you need to add the time for any pit stops at one of the Area di Servizio, for bio breaks.

The train from Chiusi to Naples is 3h 15m to 3h 45m, but then you need to add the last leg on the Circumvesuviana train, that between train transfer and train ride will take another 1.5 hours. Taking a private car service could save you the pain of the crowded Circumvesuviana commuter train, but won't save you any time, from the Central station in Naples to Sorrento a car is not any faster than the train.

The travel time is similar, however if you select the train option, you must rent from Avis/Budget because that's the only rental office in Chiusi. Also there is some value in not having to lug your suitcases aboard trains and across the station in Naples. If you drive, you place your suitcases in the car trunk in Pienza, and you pull them out at your hotel in Sorrento and after leaving your luggage at the hotel, you can return the car at the Sorrento car rental office (Hertz and Europcar are across each other on Corso Italia, Avis-Budget is on the same street but a few hundred meters before, coming from the freeway). However it is also true that some find driving stressful, and the train is more relaxing in that case.

In terms of cost, with 2 passengers, the car is slightly cheaper.

It's up to you.

“From Chiusi to Sorrento is nearly 4.5 hours' drive, to which you need to add the time for any pit stops at one of the Area di Servizio, for bio breaks.” To that add a half hour to return the car, 15 minute cab rife to the hotel. So 5:15; 6 hours including breaks.

So leaving at say 8 you are in the hotel at 2PM.

The train from Chiusi takes 3:30 to Napoli Centale; from there about 1.5 to Sorrento, driver to the hotel.
You arrive at the station 15 minutes ahead of the train, allowing 30 minutes to return the car, 1 hour to drive from Pienza. So that’s 6:45.

The first Chiusi train you can take arrives in Naples at 2:33.

The lesson: don’t plan a trip going from the Val d’Orcia to Sorrento in one day.

Ok - maybe we should scratch Sorrento and stay for 4 additional days in Tuscany. We realized Sorrento would be logistically challenging during the initial planning stage. 8 days in Tuscany is a good alternative.

How about 4 in Chianti and 4 in the Val d’Orcia.

If you were in Phoenix for 8 days, you would not go to the Grand Canyon because its 250 miles away?

I am sure you can find interesting things to do in Tuscany, but is ~ 260 miles really that burdensome?

I so enjoyed Sorrento and Pompeii that I cringe at your missing out for what is a relatively short distance.

I also like the Sorrento peninsula (including the Amalfi coast, which is the southern coast of that Peninsula). Whether you take the train or drive is up to you (in your case, since you already have a rental car, I’d drive but that is me). Lots of people visit Los Angeles and then drive to Yosemite National Park (which is 25 miles farther from LA than Pienza from Sorrento), so I think it would be worth it.

It depends a bit on how much you want to see another part of Italy. Tuscany is lovely. Sorrento and the surrounding area is lovely and different from Pienza.

My travel style is to move around a bit so I can see and experience other areas. I’m not a hopper from place to place but I’m not a “lingerer” either.

I can see pros and cons to driving and taking trains, so that’s a preference call. Some discourage traveling about , saying that you lose days while traveling from place and it’s true that you lose a calm day sightseeing. However, you can have great experiences traveling on the train or car such as seeing how locals moving about, talking to others, seeing the countryside, etc. it’s part of the adventure.

I say make sure you pack light and then go. Explore!

Is this your first time to Sorrento?

Thank you for all of the advice! We have opted to drive to Sorrento- not sure why I seem to be taming my adventurous soul as I get older….