We're upper 40's/50 and going in October. First visit for both of us.
We're booking via
Your Own Italy which was recommended via another thread. THey book 'choose your own adventure' type tours for singles up to groups. You determine where you want to go, what you want to see/activities you like, etc. The owner (Carmen) then arranges transport in the country based on your budget and needs - i.e. - are you fine taking a train from point A to B but prefer private car service from B to C, etc. She also books any group or private guided tours you'd like, including art, archeology, cooking classes, restaurant walking tours, etc.
Edit to add to last paragraph: her site has a bunch of itineraries with costs, but she told me those are really just templates for ideas. She did say the pricing was accurate (as of 3 months ago when I first spoke to her). if you say "I want to see the Colosseum" the intinerary she provides will have the same description you see on the site. I should have our quote back any day now. She also noted that the tours/days of tours can be rearranged and I'm not pot committed to the exact itinerary as of today. I'm sure there will be a "can't change after this date" but with it being 3.5 months away there's still flexibility to change stuff.
We'll be there 9 nights and are staying exclusively in Rome to check it off the list. We're going to stay in 2 different hotels so that we have different areas of the city to explore on our own for each half of the trip. Initially looked at tours that take you all over the country or only 2 or 3 primary locations. We decided we'd rather stay in an area and absorb it as much as possible instead of changing hotels every other day and never getting to settle into an area. We'll take day trips to Pompeii/Herculaneum, another to Hadrian's Villa, etc.
It is just my wife and I, not a larger group. We're scheduling in open half days, currently our last full day/night wide open, etc. We can always pivot later as needed.
I also have a stack of Rick Steves books to start working through - a pocket guide to rome, his full newest edition of Rome, and Italy for Food lovers.
Sorry I can't provide any "this was great, this wasn't worth it" for you now but I'll definitely have a post trip report after we return in mid-October.
Staff - take out the trash.