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When I contemplated what would be the best way to immerse myself in Italian during my week in Italy, I decided I didn’t want to take formal classes. I am already doing that four hours a week in DC and I didn’t want to feel boxed into a curriculum when I could be out and about exploring. What I settled on was setting up tours with private guides who would speak in Italian but be able to explain things in English when I didn’t understand. And since they were private guides and I was the only one on the tour, I could ask them to slow down and help on points of language without feeling sheepish.

It is hard online to sift through all of the corporate results when looking for private tours. I wanted to deal with humans not a company or a website. One of the most promising boutique tour outfits that I came across was Bella Milano Tours run by Mirella Maestri and Valeria Andreoli. They offer all kinds of specialized tours related to food, fashion, history, etc. that go beyond the obvious things to see or do in Milan. And even better, they will create a bespoke tour so you can really dive into what interests you. When I emailed them about the possibility of creating an opportunity to have an Italian conversation with Italians over a good meal, Valeria was quick to write back with some options.

What she set up was a lunch at Trattoria Madonnina with her friend Donatella who is also a tour guide. Now this is the kind of restaurant I would probably not have ventured into on my own. Yes, I was trying to immerse myself, but I would have been intimidated by the fact that it was full of locals without a tourist in sight. It was a wonderful spot to pretend I was a local. There was a large party that arrived while we were there that included a young man wearing a crown of laurel. Had I been on my own I wouldn’t have had a clue what was going on. Thanks to Valeria and Donatella I got the inside scoop. Not only were they able to tell me that he had graduated from university that day and was there with friends and family to celebrate, but I got to know more about how universities work in Italy. Valeria also had lots of ideas for finding sweet treats in Milan. One of her specialties is a food tour of the city center.

Since I wanted to have as many experiences as possible, I also emailed a promising looking small tour company called My Private Milan. Owner Fabio was fantastic and set me up with private tours of three different museums I wanted to see.  Since my goal was to listen to and speak Italian and to feel a bit more like a local, I asked if I could have two-hour tours at La Pinacoteca di Brera, Museo Poldi Pezzoli, and Pinacoteca Ambrosiana on three successive days rather then some other kind of highlights tour. What amazed me about what Fabio was able to set up was that each of the three guides (Paolo, Fiamma, and Davide) knew so much about the history of the museums and their collections. If they know half as much about the rest of the city their brains must be enormous.