a personal connection with a guide would be great.
Ruth, problem is that most guides also need to be pre-booked, and their fees are usually non-refundable if you cancel day-of. If flexibility is a must, then you need to rely on attractions that don't involve any advance entry fees or pre-reservations, or those that have easily obtainable tickets on the spot.
A suggestion for an underground tour that doesn't need to be pre-booked? Take a look at the catacombs of San Callixtus or San Sebastiano out on the via Appia Antica. You can walk in (on the days/hours they're open) purchase a ticket, and they'll put you on the next English-speaking tour. Wait times vary. These are very, very old and very interesting subterranean burial grounds. A prior thread from earlier this year with my links:
https://community.ricksteves.com/travel-forum/italy/catacombs-in-rome-3fe5a1cd-718f-4829-98c7-36f4f41344a8
While you're out on the Appia, you might want to explore a bit more of it? Most of what's along its length is free or have just small entry fees, Another recent thread with links:
https://community.ricksteves.com/travel-forum/italy/via-appia-antica-appian-way
I'll echo the vote for Ostia Antica: easily done on whim and weather! Rick has a self-guided audio tour and map (has one for the Appia too).
https://www.ricksteves.com/watch-read-listen/audio/audio-tours/italy
Yes, for the high-up view go to the Victor Emmanuel monument. No advance tickets needed.
Rent a surrey or bike to explore Villa Borghese? Fun for all ages and range of abilities, and there are a couple of rental places in the park (Bici Pincio; Ascol.)
Churches, churches, churches! The biggest bargain in Rome 'cause almost all are free, and almost all of the them are interesting in one way or another. For instance, I'll send you to very old lady Santa Sabina, up on the Aventine (free), for a look at a church that still retains its layout as a 5th-century basilica. The Orange Garden next door affords a nice view of Rome, and there's an interesting view of the backside of the Palatine on the walk up the hill. Peer through the keyhole in the gate of the Priory of Malta while you're up there too,
https://www.turismoroma.it/en/places/basilica-saint-sabina-allaventino
https://www.turismoroma.it/en/places/savello-park-or-orange-garden
https://turismoroma.it/en/places/villa-magistrale-sovereign-order-malta-aventine
Another underground adventure would be San Clemente: a church built upon the foundations of an earlier one, which in turn was built upon a Mithraic temple. The issue is that pre-bookings appear to be mandatory now but in March it may be possible to do that some morning in Rome - whilst waiting for your son to get up - if there are still openings for that day.
https://www.basilicasanclemente.com/eng/
The Colosseum does have two outdoor ticket booths for visitors who didn't make reservations in advance but I would make that slugabed get up early to stand in line with you; tell him if he REALLY wants to get inside without prior reservation, he'll have to rise and shine! You both have to be physically together to buy tickets, have legal IDs on you, and be able take whatever entry time they give you. I would guess that they do not sell tickets for the underground; those are the most in-demand ticket in Rome, and they sell out online within minutes of availability. Whatever you do, do NOT buy tickets from random individuals on the street. All tickets are nominative, meaning they'll have your ID info on them to prevent scalping.
Your young person will be free but they'd provide an entry ticket for him.
https://colosseo.it/sito/wp-content/uploads/2023/11/Biglietteria_Ticket-Office_Colosseum-scaled.jpg
(This is the official website but is only active the hours the colosseum and associated attractions (Palatine, Forum) are open)
Just a start? :O)