I visited Milan expecting a city that revolved around business suits, designer labels, and the occasional Da Vinci masterpiece (read: The Last Supper).
To be honest, Milan isn’t exactly the first place that comes to mind when you think of Italian charm – it’s no Rome, Venice, or Florence. But within hours of arriving, I realized I had completely underestimated the city.
Milan has a unique energy that sets it apart from the rest of Italy. As the country’s financial and fashion hub, it has an international flair. But if you walk through certain neighborhoods, you’ll be transported to the scene of a classic Italian movie. Cobblestones, trattorias, et al.
While popular attractions like the Duomo and Da Vinci’s “The Last Supper” are iconic, this article focuses on 7 unique experiences no Milan traveler should miss!
1. Take a Selfie with the Middle Finger
You read that right. What you see in the picture above is a giant middle finger unapologetically standing in the heart of Milan.
Officially titled L.O.V.E.(short for Libertà, Odio, Vendetta, Eternità or “Freedom, Hate, Vengeance, Eternity”), this provocative statue was created by renowned Italian artist Maurizio Cattelan. It was designed in the wake of the 2008 economic crisis and has been a controversial symbol ever since its creation in 2010.
The sculpture stands in Piazza degli Affari, directly in front of the Italian Stock Exchange (Palazzo Mezzanotte).
What’s worth noting is that the statue faces the people, not the building. While the artist never went on record to explain the idea behind it, you could say it signifies that the Stock Exchange is flipping a finger at the general population of Italy. Many interpret it as a satirical critique of capitalism and the financial elite.
In addition to being the shocking photo op that it is, L.O.V.E. is also symbolic of Milan’s edgy, avant-garde art scene – which in itself is immensely inspiring.
2. Feel the Creeps at San Bernardino alle Ossa
If you’re drawn to eerie yet fascinating places, San Bernardino alle Ossa is a must-see.
While completely unassuming on the outside, this church houses a macabre side chapel, the Ossuary, which is adorned with the skulls and bones of some 1,375 individuals who walked the earth centuries ago!
Believe it or not, these skulls and bones are preserved here to decorate the interiors as a way of paying respect to the deceased.
The practice originated in the 13th century when the nearby cemetery ran out of space. To make room for new burials, older skeletons were exhumed and moved to this ossuary.
Eerie as it sounds, the chapel reflects a medieval comfort with death that can feel alien to us today. In an era when life expectancy was low and mortality was a part of daily life, these macabre decorations symbolized respect for the departed and a reminder of life’s fragility.
Protip: Pair your visit with a stop at the nearby Duomo for a mix of the sacred and the surreal.
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3. Discover An Underground World at Crypt of San Sepolcro
Beneath the bustling city streets of downtown Milan lies the Crypt of San Sepolcro, a hidden gem that’s part spooky and part time-capsule.
The crypt is tucked under the Church of San Sepolcro, a relatively unobtrusive building that, if you weren’t paying attention, you might walk right past without a second glance. But descend a flight of stairs, and suddenly you’re in another world with dimly lit chambers, weathered stone walls, and a palpable sense of history.
The centerpiece here is the stone floor, which once formed part of the Roman Forum of Mediolanum, Milan’s ancient predecessor.
This is not a place overrun by camera-toting tourists. It’s a peaceful, contemplative corner of the city – right in the heart of the city (and a stone’s throw away from the Duomo!)
Protip:If you visit, also consider popping over to the fabulous Ambrosiana Library, a short walk away.
4. Explore the Contemporary Art Scene at Fondazione Prada
If you’re one of those people who think contemporary art is just a bunch of abstract splashes on a canvas, Fondazione Prada might just change your mind.
Housed in a former gin distillery (because why not?), this museum is as much about the building as the art inside. The space is a quirky mix of sleek modernism and industrial charm, with exhibitions that push the boundaries of what art can be.
You’ll find some mind-bending installations and sculptures that may leave you agape.
And the resident bar, Bar Luce, designed by filmmaker Wes Anderson (!), is a pastel-colored dream with a unique vintage appeal.
In a city known for its classic Renaissance art, Fondazione Prada is a detour into something completely different. Plus, it’s only a short metro ride from the city center, making it an easily accessible yet offbeat stop.
5. Visit Navigli: the Venice of Milan
When you think of Milan, canals probably don’t spring to mind. Fashion runways, sure.
Yet here we are, in Navigli, Milan’s charming canal district, designed in part by none other than Leonardo da Vinci. Yes, that da Vinci. Because apparently being a genius painter, sculptor, inventor, and general overachiever wasn’t enough for him.
Originally created to enable a water transportation system, the canals now lend themselves to a whole perfect setting complete with cobblestone streets, vintage bookstores, and really cool cafés.
The Navigli district is not only charming and picturesque, but it’s also lined with some amazing bars and nightclubs. It’s the perfect setting for getting a drink or watching the sunset – or both!
My recommendations for bars to stop by in Navigli are La Vinera (an authentic wine cellar where you can choose from a variety of freshly distilled Italian wines) and Rita & Cocktails (mindblowing cocktails and a snug bar feel).
Protip: Visit on the last Sunday of the month for the Navigli Antique Market.
6. Partake in the Apertivo
While the dictionary might describe an ‘aperitivo’ as a pre-dinner drink designed to stimulate the appetite, in Milan, it’s a full-blown cultural ritual.
Here’s how it works: you order a drink – perhaps a spritz, a Negroni, or a local classic like Campari and soda – and with it comes complimentary access to a buffet of finger food that could rival some small weddings.
Yes! I mean free. unlimited. Italian. snacks.
It’s not just about the free food (although I for one ain’t complaining!). Apertivo is an opportunity to do as the locals do – pause, socialize, and soak up the city’s brilliant energy. It can also be a way to save a bit on dinner.
Some top spots to try Apertivo include the Navigli district, with its canalside bars, or Brera for a fancier experience.
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7. Spot Murals in the Ortica District
If you’re after something genuinely off-the-beaten-track, head to the Ortica district.
Once a gritty industrial area, it’s now home to some of Milan’s best street art. The neighborhood has transformed into an open-air gallery, with huge, vibrant murals decorating the sides of buildings.
I’m no art connoisseur but you can’t miss the bold messaging intended behind these. There are depictions representing Milan’s working-class roots, local music icons, and even global legends.
Why is it unusual? Ortica is a part of Milan that most tourists never see, so it’s a truly very local experience. It also offers a raw glimpse into the city’s artistic pulse.
Protip: Grab an Ortica guided tour to fully appreciate the stories behind the artwork.
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