Italy and Greece in 3 weeks with teen

2 nights traveling toward Cinque Terre, seeing high lights Florence, Naples, Pisa ?

Naples is SOUTH of Rome; Pisa, Florence & CT are North.

By late June all your destinations will be filled with folk like you, ( i.e. tourists.) so how much "of a relaxing and cultural trip" it will be is uncertain. Just be prepared to have lots of other tourist folk around.

Yeah that 2 nights between Rome and CT needs some work, but looks doable otherwise. See if there are any flights to Santorini from Genoa or Pisa--might save you some time. (Note they could be seasonal flights)
When/where are the classes? You only have two full days in Rome, so that could be tight.
If your daughter does not like hiking, be sure to plan some activities for CT.

Welcome!

How many nights do you actually have for this trip not counting your overnight flight to Europe?

If you fly from Rome to Santorini you will probably need to stay in Rome the night before

Could consider traveling onward to Florence once you land at FCO then put your Rome nights all together mid trip

Something like
Land in Rome
Florence 2 nights
CT 3 nights
Rome 3-4 nights
Then on to Greece

You can stop in Pisa on your way to or from CT
Naples is obviously the wrong direction
Expect large crowds everywhere
Book CT as early as you can

Thank you for the responses! We do not have anything booked yet, trying to figure out a rough itinerary and we are very flexible. We understand this will be high tourist season, but summer is our only option with school.
We would like to fly out on June 13th and return home on July 3/4.
We are also considering just doing Greece, but really liked the idea of seeing a little of Italy, plus I read Italy is more affordable and easier to get around?

I love the idea of either moving Rome to the end of the Italy portion prior to flying to Greece or fly to Santorini from Florence, those
flights were similar in price and time.

For the 2 nights to CT, I mixed up Naples and Siena, I have been researching so much everything is running together at this point. We are considering Siena, Pisa, a day in Florence just to get a sense, maybe Orvieto.

My daughter and I loved Florence. I hope you can go!

pbscd, What were your daughter's favorite things in Florence?

Uffizi Gallery, definitely! But she loves art. We went to the Accademia that morning (it was amazing) with our tour group, and the guide mentioned something about the Birth of Venus by Botticelli, which is at Uffizi, and the guide said it was about a 20 minute walk from the Accademia. But I also wanted to see Galileo's and Michaelangelo's graves at Santa Croce, so we stopped there on our way, I do recommend it, and then had about 2 hours at the Uffizi. I was so exhausted but I'm really glad we went, and she was grateful. It ended up being a highlight of our entire 13 day tour. She stood by the Birth of Venus painting a good 20 minutes just studying it. I was hoping she was enjoying it (she's not a super demonstrative person) but she was loving it. Then in the room next door, was his Spring, and of course that needed some time to study. But it was amazing seeing so many paintings in person that we've only ever seen prints of! Now we're planning a trip to Paris, primarily to see the Louvre and 7 other art museums. It was all wonderful, truly, and I'm so glad we could experience it. Florence is very very walkable. I actually heard recently on a podcast that Florence produced such a great number of thinkers and artists and this may have been in part, due to the thinking time they were provided while walking.

Edit: she was 14 at the time of our trip.

A few years ago we flew on Easy Jet to Mykonos from Milan. Easy Jet also flies straight to Santorini in season. Having survived Rome in 2023 (which WAS one of my favorite cities with many visits in the past) I wouldn't want to double back to fly out to Greece. Milan from Florence or CT is not a bad train ride. We personally prefer Santa Margherita over CT. While you don't need to go into every museum I think Florence should not be missed or seen in a day plus there are a lot of students which makes it more youthful city. We actually find Greece a better value and a lot of time easier to get around . Your daughter should enjoy Naxos with the beaches, cafes, promenades and very nice Greek people. We then took the quick ferry to Paros with crystal clear water and beaches and then Athens. Just some quick thoughts from a mother of two now grown up daughters who enjoyed many trips to Europe.

I was 15 the first time I was in Italy. I met my wife on that trip. She was 14 at the time.

I think your family needs to have a conversation to more clearly define interests and expectations.

Lots of your plans will be determined by transportation. Getting to and from the major cities is easy by train or bus. Seeing the charming hill towns of Tuscany or Umbria pretty much requires a car. For us there's two Italy's, the major cities of Venice, Florence and Rome, then there's the countryside and charming villages and towns. To really experience Italy, you have to experience both.

What is the draw of CT for you? Outside the picture postcard views at sunset, there's really not much there. CT in July will be a horror show. It will be overcrowded, especially on the days the cruise ship day trippers show up. Italy has so much more to offer to spend your limited time resources on visiting CT. Consider here instead.

When you plan, take into account the time it takes to move from one place to another. Moving often is a major time suck, eating up most or all of a day for each move. Run several itineraries in detail, calculating how you'll get from one place to another. Also budget in at least 2 "down" days at the end of the week where you have a clear calendar and can just decompress.

I think our main goal is to experience some of the top sites in Italy just to get a taste (with the idea of returning for a more in-depth stay) and pair it with a more relaxed greek island trip, mostly because we are a water family and this is my daughter's main interest.

Her #1 destination is Santorini. I figured because it's so touristy, we would just fly there from Italy stay for 2 nights so she can get her Instagram photos, then ferry to closer islands (Naxos looks great) without cruise ships.

Karen, Do you think our time would be better spent skipping Siena and concentrate on Florence? It looks like Pisa is an easy half day stop on the train north.

We all 3 wanted to see Cinque Terre, plus thought it would be a relaxing part of the Italy trip (more water, less site seeing), but I have to admit the other Riviera towns you both mentioned seem just as amazing and I love the idea of a little less touristy location if that is possible in June. The further north riviera towns would put us closer to Genoa to fly to Santorini.

we are a water family and this is my daughter's main interest.

Where do you spend time at the water? Make sure you are aware of the differences between European beaches and southern US beaches. I was used to going to Daytona Beach as a teenager and when we arrived in Nice when I was 15, I found a totally different experience. The beach was pebbles and the water was cold!

Have you considered doing Greece first?
The temps really climb in Greece in late June