Traveling with a family

No, that's a reasonable itinerary, especially if you have closer to three weeks. For the end of June, you might want to begin settling on which days you'll be where and think about reserving hotels. But you're starting with plenty of time to plan, and there are a number of folks here to help.

Almost tight for two weeks. For three weeks, you might be able to squeak in one more short stop.

Any other places we should think about visiting? Milan, Pompeii, other?

I'd say your itinerary is doable especially in closer to 3 wks. For example, Orvieto & Ostia Antica would be great day trips from Rome. From Florence, you could day trip to Siena & San Gimignano. From Cinque Terre, explore some of the nearby towns such as Portovenere & Camogli. In Venice take the boat to Burano for half a day. I would plan on a minimum of 5 days in Rome; there's so much to do there.

If you can fly open-jaw, it will maximize your time so you won't have to backtrack to catch your return flight. Have a wonderful trip.

Check the multi-city function for flights into one city and out of another-saves time and money by not backtracking (open jaw). Also, for that time of year, A/C is a must.

Check the multi-city function for flights into one city and out of another-saves time and money by not backtracking (open jaw). Also, for that time of year, A/C is a must.

I concur with the others. With 3 weeks (essentially 19 days since you lose a day on either end to the flights), you can do your four choices quite easily and probably add one more thing. If you only have 12 days, however, it'll be a push to get everything in. As the prior poster suggested, look into an open jaw aka multi-city flight, probably into Rome and out of Venice or vice versa.

For variety, I would actually not recommend Milan or Pompeii, as the former is a large city and the latter is somewhat out of your way. Consider visiting a smaller city/town, such as Siena (easily done between Florence/Rome), Lucca (between CT/Florence), Orvieto (between Florence/Rome), or Verona (between Venice/Florence).

We are planning on flying into Milan and flying out of Rome but nothing is set yet. I would love to visit a smaller town or city that has alot of history and culture that I can get to by train. Any ideas?

If you are going to Venice, fly into Venice and out of Rome or vice versa.

It's Italy--everyone has a lot of history and culture. :-)

I'll throw Orvieto out there again. It has a lot of Etruscan history (pre-Romans), and a magnificent Duomo and an interesting double-helix well that were built in the middle ages. It's situated on the rail line between Rome (about 1 hr away) and Florence (about 2 hrs away).

I have taken my (then) 14 old son to Europe, and my (then ) 11 yr old daughter .
What I discovered is kids enjoy seeing things they have heard about.. most kids have heard about places like the Coliseum,, or at least they know about gladiators,, this sort of background info makes sites far more interesting. Kids are not as much into "atmosphere" type sites,, meaning sitting in a lovely village square sipping a drink at a quaint cafe is not quite as enthralling an idea to them as it is to average adult,, LOL

So, with that in mind I would do two things, first ASK son what he knows about Italy, what interests him,, and second ask him to do a bit of online research himself. I told my kids they were very lucky to get international travel,, and I expected them to contribute to the trip,, NOT monetarily,, but by finding and suggesting some sites for us to see. Both were able to do this, and I see no reason your son couldn't.

Ps. With all that in mind, I would not skip Pompeii,, as most kids DO know about it,, or at least find the whole volcano thing fascinating,, far more fascinating then say the history of the Catholic church, which , if going to Italy,, it does help to have a clue about. LOL

Sounds like plenty of time. Spend most time in Rome - LOTS to see. Since you're mostly in the north, I strongly agree with the other poster's recommendation of Ostia Antica. It's about a 20 minute train ride from Rome. Detail are in Rick's book. It's an ancient, abandoned city like Pompeii, but with more access and far less crowds. Get a picture of your son on a 500bc toilet or behind the bar in a 500bc pub. Don't allot too much time for Venice. The Burano boat trip posted by another reader is a great suggestion. Also have plenty of time in Cinque Terre for hiking and maybe a boat ride. You can also scuba there. You might also consider an agriturismo where you could maybe do some farm activities.

With a 13 year old Pompeii and Ostia Antica are two destinations that come to mind first.

To reiterate an earlier poster -- stuff the kid has seen on TV -- so stopping in Pisa on your way from the Cinque Terre to Florence (while I don't normally recommend...) I would recommend stoppin for a 13-year old. It seems to me that some of the most touristy / hokey stuff is a lot more fun when children are in the mix -- so while I'd never do a private gondola ride in Venice with just adults, I'd make it a priority with a kid.

I'd also recommend at least three ice cream stops a day in Rome...