Looking for thoughts/comments on our itinerary

Looks like you've done thorough research!

I would add some time in Lucca to your Pisa sidetrip. Pisa's major sights can be seen in about two hours (not counting travel time), in Lucca you can rent bikes or walk the wall surrounding the town, climb the tower with the tree on top of it, and enjoy the city. I would get to Pisa early in the morning and go to Lucca for lunch - better selection than the restaurants near the Tower.

In Firenze, you can go to the Fortezza or to Piazzale Michelangelo for great views of the city.

Orvieto will take most of a day: about 2.5 hours travel (roundtrip) by train; in addition to the castle ruins and Saint Patrick's Well, the Duomo is beautiful, there are several other churches to stop by, and it's also a good place for lunch or dinner. There are Etruscan ruins at the bottom of the hill.

In Milano, you can go up to the roof of the Duomo (elevator or stairs) and have some face-time with the gargoyles.

Thanks Zoe. The research has been a bit overwhelming. We just booked the tickets in November, so I haven't had that much time. Maybe that's a good thing but it's crazy all the research you can do. I had read that Lucca is a nice side trip as well. That sounds like a nice day.

If you decide to reserve for the Accademia or Uffizi galleries in Florence, note that they're both small, compared to the Vatican or Louvre Museums. At the Accademia, you could see Michelangelo's David and Prisoners and be out in half an hour. Two hours is enough to see most items in the Uffizi. See also Rick's free Audio Tour downloads for both city walks and museums in Italy.

You done good, tbrenk73. I think it's good to include Orvieto as a day trip from Rome, so you can all experience a small ancient hill town. Lots of choices of things to do there, a gorgeous Duomo facade, and good food. It is a 70 minute train ride from Termini, then a fun, quick Funicular ride from across from the station up to the old town. From there you can walk all the way uphill to the Duomo square in about 10-15 minutes, or catch a local bus which might take more or less time, depending on which route they take. I agree with Zoe that you could add Lucca on to your trip to Pisa. It is another very liveable small town with a variety of things to see and do. It is surrounded by a very surprisingly wide wall, and you can go up on the wall to walk, run, bike or picnic. You might follow Zoe's suggested schedule that day, or I was thinking of going to Lucca first thing, explore, eat in a restaurant or pinic on the wall, then catch the 30 minute train to Pisa and catch the Tower complex in the lovely late afternoon light. Some, maybe all, of the trains from Lucca to Pisa stop at a small station about 3 blocks from the Tower. If you want to climb the Tower, that will take more time, and you may need advance timed reservations, but maybe not in mid-April. Get back to Florence for dinner and the evening. In Florence, the Accademia Museum is indeed small in size, very impressive with the David and other excellent sculptures, and also has a museum of very old musical instruments in it. I think you might find the Uffizzi quite large tedious. When I was there 18 months ago, there were extensive renovations going on, many rooms were closed, and it was hard or impossible to locate some of the prime works. If you are not museum people, and with a 13 year old, I would skip it. However, nearby is the Galileo Science Museum, which is supposed to be fascinating, including for kids. I have not been there, but check out the reviews. And, so far, no one has mentioned gelato!, My two mottos in Italy: (1) when in doubt, eat a gelato! and (2) when you need a bathroom, order a gelato, ask to use the restroom, then pick up your gelato on the way out! Enjoy!

You seem to have given considerable thought to your itinerary. I just want to emphasize a couple thoughts from many of the posters.

You probably will not want much time in Pisa: the leaning tower and the Duomo are the two sites you are and may be interested in.
When in Florence, you may want to go Accademia just for Michelangelo's David (small time commitment, but perhaps the single most incredible piece of art that I have seen in all of Europe.
Piazzale Michelango does give the best views of Florence.
Orvieto is wonderful and there more than one tour of the caves. Make sure that you do the guided tour.

You may want to visit Capri; there is a small hike/walk to Tiberius' villa. This is more about the walk, the ruins of the villa are interesting, but definitely not a tourist magnet. Very limited explanations, but the views are amazing and the walk goes by many homes on Capri and you see the small but beautiful private gardens.

The Pantheon is a small time commitment and free look at a 2000 year old structure.

I hate to say to bypass the Vatican museum and head directly to the Sistine Chapel, but if museums are your thing, you may want to head directly to the chapel,

The Borghese Museum only allows 2 hours/visitor and the Berninis are amazing. Alternately, you may want to go the Villa Borghese to ride bikes, walk through the park, go to the zoo.

Spend a leisurely amount of time at an outdoor cafe and don't just drink the cappucino or espresso, but linger, enjoy it and soak up the surrounding (your 13 year old may not have too much fun with this).
Just tried to give you a few non-museum ideas.

I would encourage you to involve your son in planning/learning about where you are going. He might be interested in climbing the leaning tower (it does lean), or the duomo. It gets much more interesting if you know some of the background and know what you want to see. Otherwise any museum turns into famous paintings blah blah blah more famous paintings without forming any lasting memories. I think there are age appropriate books/movies that would be interesting for both him and you. Along the same lines have an idea what you want to see in the museums, there's a lot of stuff to wade through. I max out in an hour in almost any art museum so I miss anything that comes after the 45 minute mark.
I would second the gelato breaks! I think gelato is the ultimate cranky traveller fixer! Don't be afraid to change your plans if something isn't working. It's ok to sit in a cafe for an hour resting your feet and people watching instead of visiting the Uffizi.

Tbrek73,

I think your itinerary looks great!

I just noticed that you're only spending 3 nights in Florence not 4 as you posted...

On your post you say this:

4/2 Arrive 8:25 AM, clear customs, bags. etc. and train to Florence (4 nights in Florence).

4/5 Train from Florence to Rome, arriving Rome 10:35 AM (4 nights in Rome).

So you are spending 3 nights in Florence and thus you only have *one full day (4/3) to see all the sights there, especially if you decide to take a day trip to Pisa & Lucca on 4/4.

Have a wonderful trip!

In Florence, even non-museum people sometimes like the Museum of San Marco, which contains the original cells (sleeping quarters) where the Dominican friars used to live, each cell with a fresco by Fra Angelico. It's a way of seeing art in the place and for the purpose it was intended, to me more interesting than most museum collections. It's right up the street from the Accademia (Michelangelo's David and other sculptures) and both would take a little less than 2 hours (not rushing but not lingering, either).

Thanks Priscilla...I made a typo :)