First Time Trip to Italy - 9 Day Itinerary (10 with overnight layover in Copenhagen)

You won’t need or want the car in Florence and by the time you pick it up in Rome and get going it is already late morning so the time you’ll have for “exploring” Tuscany is very very little as you’ll need to get there to drop the car off
Must rental agencies will close early evening
Driving and parking in Florence is a nightmare that you probably don’t need

Could you head to Florence immediately on arrival via train?
Florence 4 nights which allows for a day trip to explore Tuscany hill towns - consider a guided bus tour?
Then return to Rome so all your Rome nights are at end of trip eliminates that 1 night stay/hotel change

I’d choose either Pompeii or Ostia Antica
Your time is already short in Rome - a day trip to Pompeii can be quite brutal with a chunk of time spent just getting there and back

I like the idea of flipping Florence and Rome, but we already have a short layover on the way from the States in Copenhagen and I think the family might balk at immediately heading to the train station on arrival after traveling for 12-13 hours. I will have to see how persuasive I can be about that.

What do you think about renting a car for the trip back to Rome if the itinerary stays the same? I should be able to return the car late at the airport and my hotel is right there.

I would balk at travel onward after flight as well!

Car for return trip to Rome could work
Just be careful about leaving luggage in parked car

Staying in the countryside would appeal to my daughters a lot less than being in Florence and tolerating a museum or two between shopping sessions.

The fun thing about art in Italy - and Florence specifically - is viewing much of it out of the vacuum we're used to seeing it here in the U.S. It's a different animal viewing it in situ, where it was intended to be, centuries ago versus removed to a blank-walled environment that doesn't reflect the atmosphere, such as the architecture, of the era. I think your teens will be impressed as long as you don't hit them over the head with it; smaller bites. :O)

Stop into a few of the better Florentine churches? It's true that what you have on the daily agendas won't fill them, even with the addition of some shopping, and there are a few that I'd recommend before the duomo as we found the exterior of that one to be more impressive than the interior. We can suggest a few if interested?

I'd love to see your gang trek up to Piazza Michelangelo and further up to San Miniato and Porte Sante Cemetery on a sunny day.

HI there, some good ideas above. Given the differences in travel styles, you may enjoy a LONG day trip to Pompeii (are you planning on doing it yourself or on a tour?) but I'm betting the teens wouldn't like it, maybe give them a day 'off' to shop and relax while you go to Pompeii? Personally, I would choose Pompeii or Ostia Antica, not both but that's just me. Here are some forum ideas about day trips to Pompeii - https://search.ricksteves.com/?button=&date_range=2y&filter=Travel+Forum&query=day+trips+Pompeii&utf8=%E2%9C%93

Wondering if you have included the teens in the trip planning and figured out how many / much time they can tolerate museums, or whatever you might have planned? Maybe they would get into it if they saw guide books and had a chance to pick something they'd like to do? Like Kathy above, I should have added the incredible art on view in churches and the opportunity to just wander, there's a classic walk between Piazza Navona to the Trevi Fountain, best done first thing in the morning before the crowds come out!

Suggest getting advanced bookings for the 'big ticket items' in Rome and Florence that might lessen the stress, including the Pantheon which can have long lines. Can you wait until you're in Florence to decide whether or not to rent a car to drive back to FCO? Not sure about one-way pricing, but that would be the easier route to add a car as you're heading to near the airport, and you could stop off at a winery on the way. Hope you have a great trip!

Thanks for all the suggestions. We did a similar trip to France two years ago for my oldest child's graduation so I have a pretty good sense for how much cultural enrichment they can tolerate per day. I try to get them invested in the planning, but they mostly just shrug. I know they have shops picked out they want to see. Otherwise it is hard to predict what they will enjoy. They all liked the Bayeux Tapestry, which shocked me. But then they all were bored to tears at the Musee de Cluny. They liked the Louvre, but obviously do not want to spend the whole day wondering through any particular museum.

I am still deciding whether to plan the Pompeii trip myself or do a group tour. I will do at least one group tour, I am just on the fence about whether to do it for Pompeii or take a tour from Florence that hits Siena and a winery. I would guess the wineries that accept the bus tours are not necessarily the ones that my wife is imagining in her head. It also feels silly to have the kids tag along to a wine tasting even if there are other stops that are more family oriented. I would be okay with them doing their own thing for most of a day so we could go on a proper winery tour, but I will have to see how comfortable the older two and my wife are with that plan.

Returning to the Piazzale Michelangelo/San Miniato/Porte Sante subject....
The reasons to consider it are threefold: The view; the church; the cemetery. All are free to visit, and none of them, individually, take oodles of time. We are all different, and your (active?) young people might enjoy the combo of indoor/outdoor attractions, as we did. :O)

The view from the piazzale is expansive.
https://florencetips.com/piazzale_michelangelo.html

The church is very, very old and has an interesting creation tale. I don't recommend visiting on Sundays when you might have to work around the mass schedule.
Hours: https://sanminiatoalmonte.it/contatti/
Some general background:
https://en.wikipedia.org/wiki/San_Miniato_al_Monte
https://florencetips.com/san_miniato_al_monte.html
https://www.san-miniato-al-monte.com

It also has a farmacia that sells products made by the abby's industrious monks.
https://sanminiatoalmonte.it/farmacia-monastica/
Translated from the website:
"In the monastic pharmacy of San Miniato a Monte it is possible to buy our delicacies (jam tarts, chocolate and lemon cakes, strudel, various biscuits), all handcrafted in the workshops of the monastery, and artistic candles in beeswax. Monastica Pharmacy: timetables Our shop is open every day generally from 10.00 a.m. until 6 p.m., with a break from 12.15 p.m. until 4 p.m."

The attached cemetery is an enjoyable wander amongst some engaging monuments and, yes, more of that view!
https://theflorenceinsider.com/porte-sante-cemetery-florence/

Maybe recover from your climb up with a glass of wine (and something different for the young folks) at La Loggia's bistro before heading back down?

Or take a golf cart tour! We have friends who did this in Florence in June. They are tourists who actually lived in Italy in the 80’s and they reported that it was great fun. We saw the carts on the street in Florence in May, and we’re wondering about them. They cost about 50E per person. I think the guide can be flexible as far as itinerary.

Has anyone been to the Museum of Costume and Fashion? My daughters expressed interest in that.

I like the idea of flipping Florence and Rome, but we already have a short layover on the way from the States in Copenhagen and I think the family might balk at immediately heading to the train station on arrival after traveling for 12-13 hours.

The train trip from Rome to Florence is almost effortless - may be a better use of a somewhat less productive arrival day. Those who are tired can nap on the train.