2 weeks in Italy with 12 year old

We took my kids to Italy when they were 13 and 11 and they loved the colosseum and forum, and Il Vittorio monument and the Pantheon. Also liked the Vatican (mainly St Peters Basilica). In Florence, we did a tour to San Gimignano and Pisa and they loved that and also seeing David at the Accademia, too. Pompeii was also a big hit, so I think you are on the right track. Add in lots of gelato and pizza and I am sure he'll enjoy it.
I would caution that you are moving around a lot, so make sure he has something to do on the trains. And pack light bc getting on and off trains can be stressful, esp w lots of luggage. We did trains everywhere and were very thankful we packed light. Good luck!

My 2 cents:

Rome – you have 2 full days, so maybe you can do “the Vatican, the Colosseum, and some other the top sites” but no real time to just wander and explore.

Florence - you have 2 full days, one for Pisa, one for San Gimignano, but no time to actually be in Florence. If all you have is 2 days, I'd spend them both in Florence.

Lisbon - from where and how are you going to Lisbon? This is extremely out of the way and a long way to go for just 1 night. Would you even get a full day there?

Sorrento - this is also out of the way and with one full day there you'd have no time to see Positano or the surrounds. I would skip Sorrento and add an extra night each to Rome and Florence.

Thanks! Lisbon is a long layover so we will just wander around and maybe check out one of the top sites.

Oh I see (about Lisbon). That's different then. :)

I also agree to drop Sorrento and add a day each to Rome and Florence. Looking back on travels with my son, other than the colosseum, I think a 12 year old would love Ostia Antica and the catacombs. From Florence, a short hop to see the leaning tower is also in order.

I would also drop one night in Milan and add it to Venice. You might want to take him to one of the places where they build gondolas and if you don’t want to kill your wallet on a gondola ride, at least take a traghetto for a stand up canal crossing.

As far as trains, Italy’s train fares mean a rail pass is a poor investment. The easiest thing to do is to go to the TrenItalia website and purchase tickets. Check the schedules and if you can firm up your travel plans, take advantage of the super-saver fares which necessitate early purchase. You’ll have to use Italian city names, not English. If you go from Florence to Pisa, there’s no need to purchase a ticket in advance since it is a Regionale train and prices are always the same.

I went with my daughter when that age and we had a blast:
Rome - we went with Through Eternity tours for their great tour - ULTIMATE COLOSSEUM TOUR WITH ROMAN FORUM AND PALATINE HILL. We also took them for the Vatican since we were so impressed with the first tour.

Not sure if you will be in Tuscany on your way to anywhere else but we did a great Gelato Bike Ride in Tuscany through I bike Tuscany. https://www.ibiketuscany.com/tours/view/gelato-ride There may be similar companies in your other areas.

We took the train from Rome to Pompeii and toured the ruins.

I would highly recommend the Free Walking Tour in Venice and getting your tickets early to the sites. We opted for Skip the Line at a few of the busier sites. One thing to check out at Saint Mark's Basilica is the Free English Tour that is given throughout the day. Look to the right as you enter the building and they usually have these started. They're given by college students from around the world that are serving through an organization that places these students at various churches in Europe for the summer. It was very informative - and free (and we ended up knowing a friend of our tour guides in Arkansas!).

We started our trip up in Venice, Cinque Terre and then made our way to Rome, Naples & Pompeii.

Have fun!

We did Italy when our daughters were 9 and 12. The biggest thing was not spending too many hours in transit--they just got squirrely. My kids were always pretty good at amusing themselves as long as they had space and weren't too restricted. They loved the Colosseum, and we rode bikes in Lucca. They liked riding the metro in Rome. If you go to Pisa, book tickets to climb the tower. There's also a mummy under glass in the Pisa Duomo. Just bring along something he can entertain himself with when he gets restless or bored. And stop for gelato.

What would your son be interested in? Perhaps he can give you some input on what he'd like to see, especially in Rome.

Pick places closer together and avoid the extra travel time.

Also, we traveled with kids while in Europe (we lived there for 4 years). They do have a limit on museum time, but that doesn't mean avoid museums. My 7 year old son was in awe of the Sistine Chapel. Just don't cram too much museum time into a day.
Take them to historical places, they will learn.

My kids loved the Eiffel Tower, gondola ride in Venice, climbing to top of the dome in the Duomo in Florence and a boat ride on the Seine.

I have asked he hasn't guven any suggestions. Then one thing he has said is he wants to go to Pisa. We will drop for lots of Gelato.

I will add my vote for dropping Sorrento. It will take too long to get there and back and you won't have time to enjoy the sights. Add the time to Rome. If Pompeii is a must-see, plan a day trip from Rome. Take an early early train to Naples, then the Circumvesuviana to Pompeii. If you have time (and energy), stop in Naples on the way back to Rome for a 2-3 hour visit to the National Archaeology Museum. In Pompeii, the RS audio tour and the sight's audio guide were just enough for me, but with a kid, a private guide for a couple of hours is well worth it. There are guides at the entrance, talk to one or two until you find one you are comfortable with (English, enthusiasm, interaction with the boy). An alternative is to do a half-day trip from Rome to Ostia Antica. You can continue to the beach from there or return to the city.

You'll have about 2.5 days in Florence. Pisa is a 1/2 day trip by train. If you want to climb the tower, reserve tickets in advance. Lucca is a good town to visit after Pisa by train. San Gimiagnono is only accessible by bus and would take at least 2 hours from Pisa just to get there.

Add a night to Venice, either one of the Sorrento nights or one of the Milano nights. Take a gondola rowing class.

2 nights in Sorrento gives you one full day. You can either see Pompeii OR go to Capri, not both. You have too many destinations. 2 nights Milan and a whole day in Switzerland is not a good plan. Drop Milan, add a night each to Venice and Sorrento.