Italy with teenage daughter

Does she like to hike or take photos? The CT area is fantastic for both.

If you are looking for open air markets, there are TONS in Florence, you can spend all day exploring the booths. Most European cites have markets on different days. I might suggest that you Google the cities you are going to to see if you can find out about the days they each have open air markets. Some are just food, some are like flea markets. All unique and different, and so much fun!
Festivals are harder to find. It all depends on the day of the month you are in a particular town. We have just been lucky with our travel schedule to see a flag throwing event in Volterra several years ago. Again, Google the towns and specify Festival and see what you get for your dates of travel. In the Cinque Terre, check into sea kayaking... we did that there and it was wonderful! you might also see if you can add a day bike trip, there are lots of these around in Florence. Rent a bike in Lucca and ride around the walls. (these kind of work if you - mom- can/want to participate with your daughter, and if she's into physical activities or not. You are going to have the most memorable trip. I took my daughter to Rome, then took my son to Munich, just me and my kid for a trip, it was fantastic. Each one different, and each one fun. I let my kids tell me what they wanted to do, and we made it happen. A tour of the BMW factory in Munich ( and lots of beer gardens and beer) with my son, a trip to Ostia Antica with my daughter (and lots of shopping with her)

Interest in museums and history depends on the person, teen or otherwise. On our daughter's first trip to Italy (she's 13 now), she enjoyed museums even more than I anticipated, and we visited some that I didn't have on my original to-do list at all! Also, even though my teen both love art and history, there are some places I feel they MUST go, because of its importance in Western history - for example, we're going to London this Spring, and I feel seeing the Rosetta Stone ("just a rock, mom") and the Elgin Marbles (she does want to see these) are important. And, your daughter may find that is interested in some of the works in museums, or some particular eras of history - you may open new doors for her! Lots of markets, food and otherwise, in Florence. I found the non-food markets a bit junky and full of t-shirts and scarves, but your daughter may enjoy. At the food market, we bought a ion of different pecorino cheeses, and had a taste-testing session while resting in a nearby piazza. Another nice experience, in Venice, was wandering into a small scarf shop, far off the tourist track. The shopowner took her time with our daughter, helping her choose the perfect color, arranging it different ways on my daughter's neck, then carefully wrapping it in tissue and a box.

I imagine the shopping alone will be the thrill of the trip for her. Whether window shopping at the high end or street markets for trinkets. Perhaps give her a budget so she can plan her shopping and knows that she can enjoy occasional purchases - and it sneaks in a life lesson ;) Definitely involve her in the trip planning, both before and during. You might be suprised at some of the things she decides she wants to do or see. Even if she isn't excited about museums, don't forgo them completely. She should be exposed to it and while she may not be excited now, the experience will stay with her. Just limit it so she doesn't get burned out. Same with churches. And let her explore on her own once in the museum or church and agree to meet up at a set time. Mix in street food with nicer meals and lots of snacks if she gets hungry. When in Nice, the beach is a must though it's not a great one. A daytrip to Monaco would be a fun thing for a teen girl. Make sure she knows about Grace Kelly before you go. A gondola ride is a must, as is seeing the Murano glass being made. She might also love climbing the tower of the Duomo.

Most of the street markets in Italy are filled with a lot of stuff that is not very good quality, you have to dig to find the good stuff. If you are in Rome I would not recommend the Porta Portese. In Florence there are a lot of markets and since Florence is known for its leather, there are leather bags all over the place. If you go to the market a lot of the stalls have an actual store that you can go in too that might have more options. There is always the designer districts in all the cities as well because Italy is known for its fashion. In Florence it is behind the Duomo and in Rome it is on Via del Corso that leads up to the Spanish Steps. It might also help the have her pick some of the activities, she might actual want to go to museums (also if this interests her, a lot of the museums do have relatively good gift shops.)