Traveling to Italy with teenagers

Try to get accommodation with a pool. Many agriturismo in Tuscany and Umbria have those. That would provide some balance in combination with sight seeing.

I cannot stress enough how important it is to have at least one place on your itinerary with a pool. I also completely agree with the suggestion of an agriturismo. They are plentiful and range from quite basic to luxurious. My teens loved hanging out in the piazza of whichever town we happened to be in, in the evening. Also, keep a look out for any festival going on.
Last summer we happened to be in Rome on the anniversary of the moon landing and apparently this is hugely popular with Italians. So much so that there was a giant street festival/concert/jumbotron in the Piazza del Popolo. We saw notices earlier in the day and just showed up for a great experience.

You don't say their ages or interests. That might be helpful. Volterra might be good if they are into the Twilight books.
I have heard about some natural hot springs that are free in the southern Tuscany area that might be fun.

In Rome my teens loved Trastevere at night.

Ours were happy when they could connect w/ friends at home. We let them go to phone/ internet banks frequently.

We just returned from a trip to Venice and Rome with our 15 year-old godson and it was fantastic!

We don't have kids of our own, so were a bit apprehensive about the idea of taking him, but it worked out beautifully. Here are my tips, for what it's worth:

1) No forced early wake-up calls, unless catching a plane or train.

2) Balance out the big sight-seeing things with low-key strolling around, absorbing the atmosphere, poking around in shops, etc.

3) Eat before everyone is plotzing.

4) We rented apartments and it was lovely to have "family space" and private space, plus a very relaxed way to have breakfast in the morning at everyone's own pace.

5) The pool idea is a good one, if you're staying in hotels or inns.

6) Be prepared for your kids to want to see the big sites, but to do it much more quickly than you might wish to. We just went with this (been there before and will go again) and it was fine.

7) Don't worry about what things you may have read about Italian restaurants getting shirty with you if you don't order 4- or 5-course meals. Not true. We ordered as much as we wished (usually 2 or 3 courses) and were treated most graciously.

Buona vacanza!

Hi, I have three boys that we have traveled with quite a bit. Not sure of the age of your teenagers but here are my tips:
1. I make sure they eat about every 3-4 hours. Italy was great because they love the food so much. But a full stomach seems to provide much happiness. So does a gelato stop or sweet stop every 3 hours.
2. The Segway tour. We booked this tour in Paris and it was very fun. My 16 yr old loved it. IT was a break from the normal walking and touring. We all had a lot of fun. Almost all the major cities have the Segway or the bike tours. On Segway there is a minimum weight of 100 lbs. and I think the age minimum is 12.
3. I always google Free festivals, events, fairs and I check to see if there are any concerts in town of performers they might like. Food markets and off beat markets with colorful people makes for a fun walk around.
4. Watch movies that might pertain to the trip prior to going. A few years ago we went to Venice and my middle son had just read "The Lightening Thief" so he was very eager to visit Venice.

5. School tie in. If my boys have recently studied something in school that I can tie into the trip I do some research to find it. So various museum exhibits or historical war museums etc can relate nicely to things they are studying and all of a sudden the topic is real to them.
6. Google research for off beat things that people recommend. I printed 5 or so pages for Amsterdam last year . The blogger was rather funny and identified places to eat and shop. My son kept asking me to refer to her recommendations. Like he really knew her and trusted her!
7. Finally if you can get your teens to do some advance research on portions of the trip. I find it helps their buy in. Even if they are the ones to make the foreign currency conversion chart for the family.

8. Tours, Walking tours, guided tours,private car tours etc. While I mentioned the Segway, I also find that small group tours can be great for the family. Enjoy

I appreciate the recommendations! Our kids are 17 and 15, well traveled, but not hugely interested in museums and artifacts all day long (which my husband and I could totally do) so everyone gave some good tips.
We are staying in lovely hotels the whole time...Mom needs a break from any type of cooking, etc.
The part of the trip they are really looking forward to is Capri because they know they can be a bit more independent, which is why we picked it and are staying there the longest.
The bike/segway tour is a good idea.
I would love to find a place for them to see gelato being made, but have been unable to find that.
I used to be a chef, so they are used to cooking, and participating in our kitchen, but I don't make gelato.

Thank you all for your replys!

PS - One thing I forgot to add - we took an iPod Touch so our boy could stay in touch with his friends. We had wireless in our apartments, so it worked out very well without the hassle of schlepping a laptop or shelling out the $ for an iPhone.

As I've mentioned before on this board, if you have teenagers and want to hit the ground with them having an interest in Italy, buy Assassins' Creed II for Play Station 3 or XBox or the PC version and have them go through it before hand. I don't normally play computer games, but this one was fun and creates several 3D cities set in the late 1400's.

Venice and Florence are very accurate as to how the game renders the cities. The other cities, not so much.

I would think that at the ages of 17 and 15, especially being male, there's a lot they could do on their own. Florence (Piazza della Repubblica) and Rome (Campo dei' Fiori) are popular with the younger folks (and older) in the evenings.

On seeing gelato being made, I'm not sure what there is to see (watching something freeze?), but as I've never seen it being made, I wouldn't know for sure. The best gelaterias (gelaterie) make their own gelato, so I guess you could ask at any gelateria that makes their own ("nostra produzione" is one of the phrases you'll see indicating this) to see their equipment, and ask if you could visit behind the scenes before the gelateria got busy for the day.

Francis is right, Assassins' Creed is a really good game to get a teenager interested in those particular cities. It worked on my 13 year old son. Now he can't wait to see it for himself.