Tuscany overnight on way to Sorrento

Orvieto ( in Umbria but good location )
Are you driving or training?

Driving I am thinking. Any recommendations for where to stay in Orvieto?

Out of the local ZTL!

Driving this route is easy. You will travel on autostrada which are like interstate highways in US. We drove from Umbria to Naples only making a stop for food in an auto grill. If you really want to stop somewhere in Tuscany, Siena is wonderful but Orvieto would be easier.

Good point. Is it better to train from CT.? Then to Sorrento?

You won’t need or want a car in CT or Sorrento
And you’ll likely have to park below the walled town of Orvieto then take funicular up if you choose to stay there

It's always better to train as long as you want to get from A to B as soon as possible, without worries about fines and parking. If you want to roam around the countryside, it's better to drive.

Driving from the Cinque Terre to Sorrento would be quite odd, but it isn't a difficult drive. There are almost no tunnels after La Spezia. It's just boring and slow, at least compared to the high speed trains going from Florence to Salerno.

What ChristineH said. A car would be nothing but a headache In 5Terre or Sorrento. As far as a Tuscany overnight, I would look for a town with easy access. Pienza comes to mind there are many others.
Brad

I was concerned about the long haul from CT to Sorrento - all day train ride. My thought was to get a car and break it up with a couple day stop in Tuscany or a midpoint.

We don’t like schlepping luggage on and off trains and find it much much easier to drive a car between many destinations.

If you want to see a bit of either Tuscany or Umbria drive. The cities that have been identified are all good choices. We have not stayed in Sienna, but have day tripped to it. We stayed near Orvieto, but not in the city, rather at a hotel at the base. Too, a tram and the a bus. Nice town.

There is no need for a car in the Cinque Terre. We had one, but parked it for the duration of the stay. We walked, took the train and boat.

We prefer the flexibility of a car and the ability to explore along the way. It is likely more expensive, but we accept that for the flexibility. We have used trains and they present their own challenges, loading luggage, on a fixed timetable.

Either way you will have a great time.

all day train ride.

What day of travel did you enter on trenitalia.com?
It's 25 minutes from Monterosso to LaSpezia, then 5 hours to Napoli Centrale if you arrive on time to take the direct FrecciaArgento that departs from La Spezia at 8:55.

Book a private driver waiting for you in Naples and you should save both time and money. He will make a stop in Pompeii if you ask him to.

For now We don't know if the new trains from Genoa to Rome will stop in Monterosso and/or will end their run in Naples/Salerno. Anyway even with the current summer schedules that are valid up to December 12, it's not always an all day train ride.

Re luggage on trains: I have never seen an aged passenger who has had to load his/her stuff on by him/herself. The trick is waiting on the platform near some young guy with less luggage than you, or having 2 middle-sized suitcases that fit in the A shaped space between the seats instead of a mammoth one per person. And no... you are not supposed to tip the young guy.

If you plan on driving, with a stop in Tuscany, this might work for you.

Pick up the car in LaSpezia and drop in Chiusi.
Then train to Naples (3-4 hrs.)

On your drive south, stop in a few towns along the way to maximize your time.
I don’t think I’d recommend Siena as parking could be an issue.

I agree with Brad, Pienza makes a nice night or two, as there are several towns short drives from there. It’s also a short drive to Chiusi.

Download this e-book if planning on driving.
Bottom of page.

https://italybeyondtheobvious.com/custom-italy-vacations/what-to-do-and-see-in-italy/

It is ESSENTIAL to give the month of travel to get the best advice about high-traffic tourism locations like those you named. For example, on-the-way stops in June or July can take 20 or 30 minutes to drive up a curving hill and wait for a parking space, like Christmas at the Mall of America.

It is not true that they are "the same-ish", but few posters here visit both CT and AC on the same trip. It's a long distance, and they do have some conceptual overlaps. One of Rick's advices is "assume you'll return". We didn't go to Sorrento until our fifth time in Italy, and we still haven't made it to CT. Usually a trip to the north might include Venice or Pisa or Milan (and the Last Supper). Are you doing any of those?

--a Tuscany overnight that would get us closer to Sorrento. --

There is no place in Tuscany that is close to a midpoint. But Orvieto is a good compromise, and has superb parking, unlike most of Tuscany. I personally would not drive from Tuscany to Sorrento, but you clearly love to be in the car. And it is true that Tuscany is best seen by car. Your driving south should take Rome's rush hour into account. That said, another place to spend the night is Tivoli, if you want to see Villa d'Este. However, that can be reached from Rome by public transportation. I only suggest it because you will have a car.

Every night we were in Sorrento (last week of May), we saw 30 cars in line, waiting to enter a big underground parking lot on the outskirts (Hotel Ambasciatori area) of town.

Have you already done research on the multiple annoyances of car rental in Italy? (I already admitted that Tuscany is best seen by car ... ) Another place that's worth visiting, and even closer to Sorrento, is Viterbo, but it's not as rich a destination as Orvieto.

Okay, so maybe car from CT out of La Spezia. Head to Orvieto drop off the car and train to Sorrento. Make sense?

Travelling September 9-25. Okay another option is we leave out CT and the need for a car. Just do train. New Itinerary: Venice 3 nights, Florence, 3 nights, Siena 3 nights?, Sorrento 4 nights, Rome 3 nights.

In my opinion, your new itinerary is good (not a fan of 5terre). I would modify it a little by taking a day from Siena and adding it to Florence. You can also just do a day trip to Siena from Florence and save yourself one hotel change.

Agreed
But I’d take a day from Siena and add to Rome

Siena is a rich destination. You may want to check which weeks that the Cathedral mosaic floor is uncovered, and plan to book or buy the right ticket to avoid a long wait to enter the Cathedral. Check climate online - could still be hot in September.

I haven't slept in Siena, but I'd want to research whether there's a bus or train to one (?) other place to go for a daytrip. I mean like San Gimigiano, but it could be a less busy town - I just mean close enough to Siena to have public transport. It could be Monteriggioni or Castellina or Volterra, or others. It's not that Siena is urban-like-Rome, but that it's a little too urban for three nights in Tuscany. Alternatively, you could book a winery tour or something like that to liven up three nights in one big town.