Everyone knows Duomo, Castello Sforzesco, Brera, and can give you advices on the “must see” and “must do” in Milan… Let’s find something different!
Here below I have chosen for you a list of 10 weird things to do in Milan, you will now terribly like experiment in Mediolanum!!!

Sports

1) Surfing in Wakeparadise! If you love surfing, this is the right place for you. I have to confess I didn’t know this place, neither, and I discovered it thanks to a Polish CS guest addicted to surf. You have artificial waves, areas to chill on a sunbed, bars… everything just outside Milan in Idroscalo Park (it is very close to Linate airport; if you come from the city, you can take the bus 73 to the airport)

2) If you’re brave enough and are coming to Milan between 25th and 26th January 2020, you can join the traditional “Cimento Invernale sul Naviglio Grande”. What’s that?! A crazy sport challenge against the winter temperatures! From 1895, brave swimmers enter the Naviglio in the coldest period of the year. Next year you have 2 options: the “traditional” challenge, on 26th at midday, and the “Lion” one, at midnight of the day before. Hot! 🙂 And it is not the only one: find here the calendar of all these events in Italy.

Culture

3) Do you love art? The disquieting Church of San Bernardino alle Ossa is waiting for you… Just near Milan University.
The Church is famous for its ossuary, built in 1210 to bury the bones of the dead from the ancient Brolo Hospital nearby, dedicated to the cure of lepers. You enter a dark corridor, and you suddenly enter to a ghostly chapel, whose walls are completely covered with skull and bones, watching you from above. They are believed to be the corpse of the Brolo lepers, but you have also evil creatures… the skulls inside the cases, in fact, belong to executed prisoners.

4) Here’s a treat for the lovers of darkness, the “Horned Madonna” in St. Eustorgio’s Basilica. This weird fresco, in one of the most important churches in Milan, has a meaningful legend tracing back to the Catharism. St. Peter martyr, during his fight against Cathars, joined one of their meetings and suddenly saw the apparition of Mary with the child, but… she had horns!!! It was actually the devil, in disguise, that’s how Peter was able to drive it away with a piece of holy bread.

5) If you arrive in Milan by train it is very likely that you end up in Central Station, classical masterpiece of XXth Century. Only a few people know that in the railway station there is a secret place, accessible to public only on special occasions (i.e. FAI special openings): it is the Royal Pavillion, a waiting room dedicated to the royal family who took the train from Milan to their royal palace in Monza. It is a luxurious space with pillars, marbles and decorations, totally in contrast with homeless people outside.

6) A mysterious garden, hidden by thick trees, in a noblevilla close to Porta Venezia. You just try to have a look inside, and here’s the surprise: ten pink flamingos around a small basin. This is “Villa Invernizzi” in via Cappuccini, a small exotic spot in the rich traditional heart of Milan.

7) Just a few kilometers from the centre, close to a metro station, you can leave modernity and go back to the past. You just need to step into Chiaravalle Abbey, founded in 12th Century by Cistercians monks, a religious complex rich in frescoes and pieces of art in the middle of the big south agriculture park.

By night

8) Tired of crowded pubs? Backdoor 43, the smallest bar in Milan, is the place for you. With 4 square metres and the same number of seats, it recalls the tradition of “speakeasy” clubs and offers high-quality cocktails, but of course you have to book in advance! (or you can have your “take-away” cocktail).
It has been opened after a nice unconventional marketing campaign: lots of thriller books, with a bookmark with the hashtag #backdoor43, had been abandoned in different spots in Milan… like in a 20’s noir!

9) Meet a ghost walking near Sforza Castle by night. This is the “most haunted place” in Milan, the center of power and intrigue. In the Museum of Musical Instruments, sometimes at night has been heard a melancholy harp melody: it is Beatrice d’Este, Ludovico il Moro’s wife, who died giving birth at the age of 24.
More disturbing is the legend of the “lady in black”. It tells how, during foggy evenings in Sempione park, many unwary young people met a lady completely veiled in black; after a night of love, they tried to discover the mysterious face, which turned out to be a skull…
If you like ghost stories, you can join one of Valeria’s Ghost Tour (really thrilling! read here my experience)

10) End the day sleeping in a real castle. Years ago, I have been for the week-end in one of this kind of accomodation, between Milan and Parma: “Tavola Rotonda” in Cortemaggiore is a magic castle tracing back to 13th Century, now a modern hotel with restaurant & SPA.

This is my list of 10 weird things to do in Milan. Do you have other weird places/activities to suggest? If you like, leave me a comment or visit my Instagram page 🙂