Tuscany - Sorrento 11 nights looking for suggestions

It’s a lot of hotel changes in Tuscany. I would choose a central location (in or around Siena) and drive to the others on day trips. From Siena you can drive to the locations you mention in less than 90 min.
Orvieto makes sense to be visited on you way down to Sorrento, otherwise it’s a major backtracking. However the drive from Siena to Sorrento is a long 5+ hours, so if that must involve a stop in Orvieto, then it might make sense to spend a night there, otherwise it would be a very long day (drive+Orvieto visit).
You could also make do with 4 nights only in Sorrento (that is 3 full days, one for Amalfi Coast, one for Capri, one for Pompeii, which you could even visit on the way there or on the way back to Rome (3 hour visit is good for Pompeii).
Which towns to visit in Tuscany is up to you, there are a tons. San Gimignano is the most visited, and at times crowded (but I doubt it in July, since July is hot and all Europeans will be at the beach rather than visit art towns) but on the other hand it’s so iconic that it is worth a visit.
PS: with children that age, and with that heat, I would look for a place with a pool. Hard and expensive to find in the historical center of Florence, but a more affordable feature outside the historical center, and in Tuscany’s farmhouses or out of town/country hotels. Use the search feature in Booking.com to find a place with a pool. Pool not necessary in Sorrento or Cinque Terre, as you will be in a beach town.

Please advise whether you have visited Europe before, and whether you have rented a car in Italy before? Where are you flying into for the earlier part of the tour. We also need to know if you mean that you are visiting Rome for a few days after Sorrento, and not just going there to fly home? It would also be helpful to add your home town to your visible public profile for this newsboard. That would help us to know how you may react to the sweltering heat and brutal sun of every single stop on the proposed trip!

One reason for these questions is that it seems odd to rent a car and then stay one night in town after town. You have only mentioned towns that are large, and actually, reachable by public transit. But that's not the point. The time and energy spent checking in and out, and parking, is a big deal. Have you put these towns into Google Maps and explored actual distances? How did you select the list of towns, besides Florence?

I realize that it is different with children, but we tried to do at three smaller towns a day in Tuscany. Do you have our host's Italy book?

You are correct that your trip is not relaxing nor will any of you get a feeling for Tuscany. You are really shortchanging Tuscany only giving it one night in addition to the three nights in Florence, before driving off to Umbria which is where Orvieto is located.
You state that you have three nights for Tuscany besides your three nights in Florence but I can find only one in Tuscany, Siena. You are skipping Tuscany!
We rented a house with pool in the Chianti region of Tuscany in June for our family. It was warm during the day, and the pool was a life saver for the children after sight seeing during the day. They loved climbing the towers in San Gimignano. Have you done this type of foreign travel with kids before?
Honestly, all you seem to be planning is checking in and out of hotels, not seeing or enjoying Tuscany. Assisi is farther away in Umbria so drop it for this trip. Save it for a trip dedicated to Umbria. What do you want for this region of Italy before heading south? Which is more important for you, northern or southern Italy? Stay in a hotel at least two nights, better yet three or four.

We didn’t go south of Rome until our 8th trip to Italy. We have always gone south in October and it was still very warm, some places were hot..

I agree with the above comments. I would reduce days in Sorrento to add to Tuscany/Umbria. Even including Pompeii, I still think I'd drop a day since your time in Tuscany is short. I think Siena needs a couple days. As currently designed, your itinerary basically includes no time in Siena since you are spending the daytime in SanGimignano. I haven't been to Assisi and really would like to go. However, it seems like a bit of a drive for just one night, and in my opinion, you don't have the time for it.

Unless you have religious reasons for going there, I would skip Assisi. I've been and was not impressed. On the other hand, the cathedral at Orvieto is a wow.

We were impressed with Assisi and have been there several times but from our base nearby in Umbria. I think your children would be very bored there.

Dear all, thank you so much for the comments!
They are very helpful!
To answer some of the questions mentioned above:
We are from Pennsylvania. Have been to Spain and French before. This is our first time to Italy. We drove in Spain and all was very smoothly. I will search a house near Siena with a pool to use as our base. What are the towns or villages would you suggest us to visit? I plan to drive the Tuscany drive loop RS suggested in the book. The loop is near Siena. That might take a day. I did not want to cut the days of Sorrento is because we want the kids to enjoy more sea town days. I’m worried Tuscany will be too hot for them.

If you were planning on taking the car to Sorrento, I would reconsider unless you are dropping it on arrival.
I think if you just consolidate the Tuscany/Umbria time, that will make an improvement.
I’m always confused why people include Cinque Terre and the Amalfi coast in one itinerary (unless you have months to travel). They have some similarities.

Concentrate on Tuscany while you have the car
I would suggest basing at an agriturismo with a POOL. Somewhere near Pienza/Montepulciano

You should drop the car and train to Sorrento ( Orvieto or Chiusi)
Driving in Amalfi area will be an expensive headache

Only rent the car for the days you REALLY need
Rates are super high this year
Be sure you do your homework on driving in Tuscany or you’ll get some unpleasant surprises when you return home
All drivers must have an IDP

Be aware that Sorrento is built on a cliff. It has only one, tiny, sand beach, which is literally between the two commercial marinas. There is a strong smell of diesel fuel there! I think the elevator down to this beach is 2 euros, or a 1/4 mile steep-sloped sidewalk for free. The most expensive hotels in Sorrento are on the cliff, and they have wooden boardwalk swimming platforms (i.e. on piles, not floating) in the Gulf, private to the hotel, reached by the hotel's elevator.

The high-priced beaches in Positano and Amalfi are 100% pebbles, and also rather crowded.

You need to rethink your "beach time" and do a little more research. I haven't been to CT, but I wonder if the beaches are better there. Also, Sorrento books up six months in advance. You will not get your first five Sorrento hotel choices ...

There are a bunch of nice beaches in Tuscany --- no need to go all the way to Sorrento. Maybe save Pompeii for another trip.

We took one of our kids to Italy in the summer when he was 9 or 10 --- his very favorite place was Venice, but a close second was Orvieto. He loved the well, the Signorelli chapel (despite having no interest in art or religion), and underground Orvieto. My husband and I returned to Orvieto last fall after 20+ years and found it just as great as we remembered. We also visited Assisi and found it rather boring except for the art in San Francesco --- I can't imagine a child liking it. If we took our grandchildren to Italy again, we would take them to Siena and Orvieto. Siena because they'd like the floor of the cathedral, the Campo, the pedestrian-only streets, and the escalators between the top and bottom of the hill.

All of the towns you mention will be stuffed full of day-trippers all day, so the more you can stay in a very popular town for a few nights, and walk around it in the morning and evening, the better.

I agree with many of the above posts. Sorrento is stunning, but I would never describe it as a beach town. I would seriously consider an Agritourismo in Tuscany as a home base. In addition to being family friendly, many if not most have pools, which everyone will enjoy after a day driving the countryside.

I have really enjoyed reading this post, lots of great suggestions and advice.

I have a question, for Florence and Tuscany, would you base yourself in one for say 4/5 nights or do you really need to stay in both to get the best of both?

leanne, many people on their first trip to Italy prioritize Rome, Florence, and Venice, maybe with one other place like Milan or Bologna. I consider Florence (and its art) an entirely different, urban, experience than "the Tuscan countryside." A car is a hindrance while seeing Florence. Even Fiesole is easily accessed by a bus from downtown. In my opinion, Florence is (is capable of being thought of as ... ) a separate visit from "Tuscany." My opinion may be more true now that tourism is up and wait times for high-level sights can be long.

I suppose everyone wants to see the David and the Duomo, but how much do you like Renaissance art? Do you go to museums at home?

We didn't go to Sorrento or Tuscany until we'd had a least brief visits to Italy five times. I mean to pick up cruises, or go to Croatia, or things like that. All that said, I do think that it is much better to have a car to visit the smaller towns of Tuscany. As I wrote above, there are some towns easily reached by public transportation. But many of the smaller towns don't warrant a full day, so they are very hard to do while visiting other towns the same day. That's a reference to radial-spoke public transportation, not a comment about terrain or crowding.

Our first visit to Italy was two-weeks, Rome-Florence-Reggio Emilia-Venice. (I had been to RE on business without my wife, it's not a priority for others. Bologna more suitable for most visitors. But you won't meet anyone speaking English in RE.)

Edit: Note that the floor of the Siena cathedral is covered with protective plywood for a large fraction of the year. Dates published, I'm sure.

Capri is a lovely visit, but it is highly pedestrianized. Children who do not regularly walk a mile or more will balk before you get to see much of the island. We didn't go to any beaches, but I think they may involve hill-climbing or other long walks. (Also a rocky, cliff-y place.) There is a big, crowded public beach walkable from the ferry, but I wouldn't waste time on that for a 10AM-5PM Capri visit. Last week of May will be plenty hot.

The towns on SR 222 between Siena and Florence would be a good location to stay. Towns we have enjoyed staying in are Castellina, Radda, Panzano(*), Greve and more! You will note that I gave Panzano a star! Most villa rentals are a minimum of one week Sat-Sat. Be sure to check than anywhere rental you book has a/c as most don’t have it.
Our grandchildren loved Siena, San Gimignano and Florence(shopping.) We were in Siena for the Palio and it was so much fun!!