In general it's doing websearches for:
- local tourist offices. Some such as LangheRoero and turismotorino websites in Piemonte are more active than others, but overall the city based ones have more esoteric options. I think the Bologna tourist office try such stuff.
- Web searches for specific interests e.g. walking groups, truffle hunting, and others here seem to find esoteric guided walks that way e.g. tour the markets of Bologna. There are also self-guided ideas e.g. again in Bologna we had a relaxing time hunting down the hidden waterways of the city. It wasn't big-ticket awe-inspiring stuff, but interesting and relaxing, taking us to lesser seen parts of the city and in general away from the main tourist sites.
- Another thought, not tours as such, but searching for city + festa often brings up different listings of local festivals and these can be a joy. From late night white/blue nights where there is street music and late night opening, to historic car rallies / rally's, truffle and other food festivals, to more historic costume / processions. It can be pot luck as to whether you time to be near one of these, but they are often really interesting / enjoyable, and it's not unusual to be entirely amongst Italians rather than tourists.
Another angle is what AirBnB is offering as an addition to their accommodation platform : "experiences" of various types, which can be anything from small tours with a local guide, concerts, courses, and what they call "social impact" experiences. Check out their home page.
Never tried any of this but certainly looks promising. The advantage is having all this variety on one site - which is AirBnB's strength in the accommodation business as well.
My husband and I are usually independent travelers, but we have done a few tours. Like Gail, we spent a delightful time with Luisella Romeo [http://www.seevenice.it/en] in Venice. She is knowledgeable and fun to be with. Well worth the expense. ...
Another enthusiastic recommendation for Luisella. One of the very best tour guides we have ever used - and we have used quite a few. She really has a gift!
Whether or not something like an AirB&B would work depends on what you want from the experience, I think. A casual type of tour, like cooking or wine-bar hopping would seem to be a good fit. On the other hand, if I want reliable information I think I'd prefer a licensed professional vs. an amateur.
Of course, I may just be hopelessly old fashioned on these matters. While I understand the convenience of the Uber and Lyft systems, I'm just not comfortable jumping in a car with an amateur driver. I like knowing that professional drivers are held to a higher standard, even if I'm kidding myself about how carefully those standards are checked by authorities.
Similarly, with tours I'd like to know I'm with someone who is educated on the subject matter at hand. As I said, some subject require less of that ... certainly cooking is something I can judge by the outcome, while if someone is giving me bad historical information I won't know unless I do some follow up work later.