I'm attempting to help plan a family trip to Italy this summer. 3 adults. We don't really need a traditional tour, but it might be useful to have a company arranging for bookings and private transfers. Is this more of a travel agent question? We were always diy travellers but are considering making it a little more plug and play for my Dad.
Cities under consideration include Milan, Rome, and Venice thus far.
I'm sure you can find that kind of service, but you could also do it for free and just hand over the info. Italy is such an easy place to travel, I'd rather use that kind of money for a flight upgrade, etc.
People here will freely offer advice once the itinerary is fleshed out.
We ran into some people in Italy that were using "UnTours". Never used myself but might be close to what you want.
Assuming you have seen this tour
It would be very easy to add on Milan at the start
https://www.ricksteves.com/tours/italy/my-way-italy
Otherwise I’d go the whole DIY route
As said above Italy is very easy to plan and you’ll get plenty of help here if you want it
We always plan ourselves, but friends of our have used a company (I think it's InItaly.com) for bookings. They have absolutely loved some of the places they've stayed. That said, I think their trips have been more off-the-beaten-track than the cities.
