After an absurd amount of research, this is what I ended up with (and it's not even original, lol!). I am taking me 13 and 15 year old daughters who have never even been on a plane.
I like to plan everything and not wander too aimlessly (except when we want to, of course!) so I try to have a food option in each area in case people are too tired or cranky to explore/choose. We will probably do takeout/street food/gelato/coffee only. Recommendations very much appreciated.
I have a detailed map saved in google with all the sites, but if I'm missing obvious things we should look for near where we already are, let me know? :)
Day 1 Rome-
Colosseum, Forum, Palatine Hill combined tour midday
Self-guided food walk through Monti, back toward Piazza Navona (home base)
Sleep early or people watch in the Piazza
Day 2-
Vatican/Sistine combined tour noon
Trastevere food exploration
Spooky night tour (This is for the teens.)
(If we are energetic or have extra time, we will drop into Castel Sant'Angelo early in the day.)
Day 3
Morning Street Art walk in Ostiense
Rental car trip to Sacro Bosco. Possible stop at Villa Lante? (I have extensive maps- printed, electronic, and saved in photos- and instructions to avoid the ZTL. Hopefully it goes ok!)
If we are back early evening, stroll by Trevi Fountain and Spanish Steps after dinner.
Day 4
Choose your own adventure options. Pick 2-3 max.
Go back to something you loved
"Crazy" exhibition at Chiostro del Bramante (top of their list),
Centro Storico Coppede walk
Basilica San Clemente (top of mine),
Pantheon
Longer options: Catacombs tour or half day trip to Ostia Antica
Day 5
Breakfast in Rome (What would you have for your last bite?). If we haven't gone by the Trevi Fountain or Spanish Steps by then, we will take an early walk.
Train to Montecatini, dinner at the restaurant I went to on my honeymoon.
Day 6
Planned to chill on Alto away from the crowds, but daughter is begging for a Florence day trip. We will gauge energy levels, but we would take a walk by the most significant Medici sites (daughter is into the Medicis/Renaissance big time. Didn't decide this til after I booked everything, of course.)
Day 7
Daughter wants to do photo shoot at Montecatini Art Nouveau sites, fountain, spa areas...
Train to Venice midday
Dinner and sunset viewing in Venice, maybe evening gondola
Day 8
Morning walking tour
lunch and book stores
afternoon train to Cinque Terre
Day 9
Hike a little, rest a little, eat seafood
Day 10
Breakfast in Cinque Terre
train to Pisa for airport. We have a couple hours to get a last bite. They will most likely want pizza and gelato if anyone has any favorites. I will not play that by ear since we have a flight to make.
Day 11
Flight to Paris (We used airwander to look for flights and found a long stopover in Paris at no cost. Planned to head home on day 11, but my daughter has told everyone she was moving to Paris since she was 4, so couldn't resist!)
Evening Seine Cruise? (cheap one, lol)
Day 12
Large mapped walking loop of big sites with many bakery stops, lol
Maybe brief guided walk through Montmartre in late afternoon?
Late (for us) dinner. People recommended Bouillon restaurants for inexpensive but "French" feeling dinner for teens.
Day 13
Breakfast in Paris
Midday flight home.
Any Bostonians? We have a 4 hour layover. If we are on schedule (big if), we are making a mad dash for Modern Pastry. From Italy to the North End (chef's kiss). Start the trip with espresso and end with a legit lobster tail from our favorite Italian bakery in the US.
If I can recover quickly enough, I will post a trip report. I know we will be going at an unprecedentedly open time since the beginning of the pandemic.
Thank you for reading and thank you for your advice to help us plan!