Five more days in Italy after Rome-Florence-Venice tour. Need help with itinerary

I assume you are starting from Venice. You could spend a night in Padova, then proceed to CT the next day. You can relax there. After 2 or 3 nights there take the train directly to Rome (about 4 hours). I think flights to the States from Rome work out better than flights from Venice. Since you will have visited Rome at the start of your trip, you may want to spend just one night there before heading for home. I don't think any of these towns are "very conservative" concerning family configurations. Go and enjoy yourselves. I love Italy and will be there in April!

Heading home from Rome is a better idea than from Venice. The flights to the US from Venice leave very early in the AM and getting to the airport in Venice is a little more complicated than in Rome.
Where to spend another 5 days really depends on your interests. I have spent more than 5 days in each of these cities and could have spend many more. But - if you want to see more of Italy, basing yourself in either Venice or Florence would afford you a number of day trip possibilities. You could also stay in Verona, Bologna or any number of smaller Tuscan towns and do day trips. RS has really sold the CT area but it's never been something I was interested in... You might want to read a good guide book to see what peaks your interest. RS does a good job with the places he covers but understand that he misses chunks of the country that might interest you.
I can't imagine a problem with your family in any of the bigger towns and maybe not in Italy as a whole.

Hi, John. You may well find that after the 9 day tour you want to spend more time in the cities the tour visited. This has always been true for us. Even the best tours just give you a taste of whatever city you're visiting. We've learned to plan extra days at the end of a tour to relax a bit, catch our breath, then enjoy our location in greater depth. Otherwise, I'm with Kathryn on the CT; I'd much rather spend more time in Florence or Rome, or take 2 or 3 day trips to Assissi, Padova... Your daughter would probably get a kick out of the leaning tower, and Pisa is reachable by public transport. Lots of options.. Buon viaggio!

Having 9 year old with you I assume that you will go when school is off. Prepare yourself it will be hot, very hot. Maybe you live in some hot areas of the States so you will be better prepared for it. But anyway their air-conditioning is not so strong as we are used to here. I don't know where your trip ends. I would suggest go to Cinque Terre. After three hot crowded cities this would be like vacation from vacation. I am sure your daughter will really appreciate it. I would recommend Monterosso out of 5 towns of C.T. It is the largest, has the best beaches and the best connection to the outside world, even some express trains stop there. You can get to Monterosso from Rome in less than 4 hours with one train change, from Florence in less than 3 hours with one train change, from Venice in 5 and half hours with two train changes. The closest big airport to fly back to US is in Milan. You can get from Monterosso to Milan in 3 hours and train is direct. I would recommend you go to Milan day before your flight and stay overnight there. Maybe you would have time to see LaScala and Duomo there. We did exactly this itinerary and it worked very well. Deutsche Bahn website is the best to check train schedule. If you want to buy some train tickets online ahead you have to use italian website.

John,

Padova, Vicenze (fairy tale town full of Palladian Architecture) or Verona and Lake Garda.

Sirmione, or Peschieria del Garda would be a good base. Easy train back to Venice.

If the tour ends in Venice, you should stay in the north of Italy.
The Veneto region offers the following, besides Venice:
Padova, Verona, Vicenza, lake Garda, Dolomites mountains (however these are better done by car)
A little to the west is the region of Lombardy: Milan, Lake Como, Bergamo. Near Milan airport is also Lake Maggiore and lake Orta. The north of Italy has so much to offer that you don't need to go far.
The possibilities are endless even without trekking back south to Rome. The Cinque Terre are not easy to reach from Venice. It's a 5 to 6 hour trip. That would be the last place I'd consider coming from Venice, even Naples is faster to reach. You can fly home from both Milan MXP and Venice VCE, respectively the 2nd and 3rd largest airports in Italy.
Somebody above said it will be very hot. I can't say the same since you don't say when you are going. July and August are generally hot. June and September less so. The rest of the year is not hot.
I also don't understand the connection between two dads traveling with daughters and conservative towns. What are conservative towns anyway? The ones that voted for Berlusconi at the last elections?

If you're looking for towns in the North of Italy, I recommend Bolzano! Bolzano isn't a big tourist town (there's not a whole lot to DO, per se), but the city is part of a region that was part of the Austrian Empire up until the early 20th century, so there's still a significant amount of German/Austrian influence in the food/language/etc. Residents in Bolzano switch from German to Italian and back again seamlessly - in the same conversation! It's fascinating.

I do agree that flying out of Rome will probably be easier, but if you are traveling in the summer, I would avoid Rome like the plague and deal with the added minor hassle of flying out of Venice.