I’ll be honest with you.
When I first landed in Milan, I thought I had it all figured out—snap a few photos at the Duomo, grab some gelato, maybe check out that Leonardo painting everyone talks about.
But here’s the thing: Milan didn’t reveal itself to me right away.
It took wandering down a random side street, stumbling into a church covered in human skulls, and sipping espresso next to a garden full of pink flamingos before I realized this city is absolutely wild.
Milan isn’t Rome with its postcard views or Venice with its gondolas.
It’s different.
Edgier.
And once it clicks, man, it really clicks.
Stand On Top Of The Duomo And Feel Tiny
The Duomo is one of Europe’s greatest architectural and cultural landmarks.
But you already knew that.
What you might not know is that climbing up to the rooftop is where the magic actually happens.
I’m talking about walking among those Gothic spires, feeling the breeze hit your face, and looking out over the entire city sprawled beneath you.
The Gothic structure has jaw-dropping stained glass windows and towering spires that took 400 years to complete, and you can climb stairs or take an elevator to the rooftop for city views.
Sure, it’s touristy.
Everyone’s there.
But standing on that roof, surrounded by stone sculptures and the hum of the city below, you’ll get why people lose their minds over this place.
My tip: Go early morning or late afternoon.
The light’s better for photos, and you’ll dodge some of the massive crowds.
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Hunt For The Giant Middle Finger Sculpture
Okay, this one’s just fun.
There’s a giant middle finger statue that sends an unambiguous message to Italy’s bankers.
I’m not kidding.
Right in the middle of Milan’s financial district, Italian artist Maurizio Cattelan installed this massive marble sculpture of a hand flipping the bird.
It’s called L.O.V.E., and it’s aimed directly at the stock exchange.
When I first saw it, I couldn’t stop laughing.
It’s bold, it’s cheeky, and it’s so incredibly Milan—a city that doesn’t take itself too seriously despite all the high fashion and corporate skyscrapers.
Snap a selfie with it.
You’ll want proof you found this thing.
See Leonardo’s Last Supper (But Book Way Ahead)
Book tickets way in advance if you want to see the Last Supper by Leonardo Da Vinci.
I learned this the hard way.
The museum housing the Last Supper is located on the northern wall of the refectory of the Dominican convent of Santa Maria delle Grazie, and this work is a UNESCO World Heritage Site.
The thing is, they only let in like 25 people at a time, and you get 15 minutes max to stare at it.
But those 15 minutes?
Worth it.
Seeing this painting in person, the details in each apostle’s face, the way Leonardo captured that moment of betrayal—it hit me harder than I expected.
My hack: If tickets are sold out, book a guided tour.
Tour companies often have reserved slots, and you’ll get context that makes the whole experience richer.
🗼 I Wrote a Book About My Japan Travel Catastrophes!
Before I landed in Tokyo, I thought I was the “Final Boss” of international travel. Spoiler alert: I WASN’T. 😅
🚅 I boarded the wrong Shinkansen and ended up in THE WRONG CITY. I confused locals with my “expert” bowing that was more awkward than accurate. I accidentally stumbled into a high-stakes Kendo practice thinking it was a tourist show. Sound like something you’d do?
“Things I Wish I Knew Before Going to Japan” is your shortcut to avoiding ALL my cringe-worthy mistakes. ✨ Inside, you’ll find practical, LIFE-SAVING tips on etiquette, transport, money, and hidden gems that will save you time, money, and a whole lot of confusion.
Wander Through The Secret Navigli Canals At Sunset
Locals and travelers flock to the Navigli neighborhood for its inviting atmosphere, delicious food, and great drinks.
This is my favorite part of Milan, hands down.
The Navigli area is centered on the two remaining canals that once encircled Milan.
When the sun starts to set and the golden light bounces off the water, the whole vibe shifts.
The canal-side bars fill up with locals doing aperitivo, which is basically Italy’s excuse to drink and snack before dinner.
I sat at a tiny table by the water, ordered an Aperol Spritz and some focaccia, and just people-watched for an hour.
No agenda.
No rush.
If you’re there on the last Sunday of the month, hit up the antique market.
You’ll find everything from vintage leather bags to old Italian posters.
Get Weird At The Bone Chapel
This one’s not for everyone, but if you’re into the strange and macabre, you’ll love it.
San Bernardino alle Ossa is a small church located near the Duomo with a chilling yet fascinating ossuary chapel decorated with human skulls and bones.
The bones were collected from a nearby hospital cemetery in the 17th century and arranged in elaborate patterns on the walls.
Walking into that chapel felt surreal.
Skulls stacked floor to ceiling, femurs arranged like decorative tilework, all lit by soft candlelight.
It’s eerie, sure.
But also oddly beautiful.
And it’s a side of Milan you won’t find on most Instagram feeds.
Peek At Pink Flamingos In A Secret Garden
This might be the most random thing I saw in Milan.
In the private garden of Villa Invernizzi, around a pond, lives a colony of pink flamingos.
Yep.
Real flamingos.
In the middle of the city.
You can’t go inside the garden—it’s private—but you can peek through the hedges on Via dei Cappuccini.
I stood there with a bunch of locals and tourists, all of us squinting through the greenery trying to spot these bright pink birds chilling by the water.
It’s one of those “only in Milan” moments that makes you smile for no reason.
Drink Espresso At A Café Designed By Wes Anderson
If you’re a fan of Wes Anderson’s aesthetic—think pastels, symmetry, vintage vibes—you have to check out Bar Luce.
This Milanese café was entirely designed by the American director Wes Anderson.
It’s inside the Fondazione Prada, which is already worth visiting for the art.
But Bar Luce feels like stepping onto a movie set.
Every detail is perfect.
The mint green booths, the retro jukebox, the lighting—it all screams Anderson.
I grabbed a cappuccino and a pastry and just soaked it in.
Even if you’re not an art person, this place is Instagram gold.
Explore Villa Necchi Campiglio’s Jazz Age Glamour
Villa Necchi Campiglio is one of the most beautiful house-museums of Milan, right in the heart of the Quadrilatero del Silenzio.
The villa was designed in the early 1930s and was the first in the city to have its own private swimming pool.
This place is stunning.
You walk through rooms frozen in time—Art Deco furniture, original artwork, a perfectly preserved outdoor pool.
It’s like peeking into the life of Milan’s elite during the interwar years.
If you’ve seen the movie “I Am Love,” you might recognize it—it was filmed here.
Grab a coffee at the bistro by the pool.
It’s the most elegant caffeine break you’ll ever have.
Hunt For Street Art In The Isola District
Milan isn’t all marble churches and designer shops.
The Isola District is known for its creative culinary scene and vibrant street art that gives the neighborhood its unique character.
I spent an afternoon just wandering the streets, camera in hand, looking for murals.
You’ll find everything from massive colorful pieces covering entire building facades to small stenciled works tucked into corners.
The area’s got a young, artsy vibe.
Lots of cafés with outdoor seating, vintage shops, and this general feeling that anything goes.
If you’re tired of the polished side of Milan, Isola’s where you want to be.
🗼 I Wrote a Book About My Japan Travel Catastrophes!
Before I landed in Tokyo, I thought I was the “Final Boss” of international travel. Spoiler alert: I WASN’T. 😅
🚅 I boarded the wrong Shinkansen and ended up in THE WRONG CITY. I confused locals with my “expert” bowing that was more awkward than accurate. I accidentally stumbled into a high-stakes Kendo practice thinking it was a tourist show. Sound like something you’d do?
“Things I Wish I Knew Before Going to Japan” is your shortcut to avoiding ALL my cringe-worthy mistakes. ✨ Inside, you’ll find practical, LIFE-SAVING tips on etiquette, transport, money, and hidden gems that will save you time, money, and a whole lot of confusion.
Try The Medieval Whispering Walls
This one blew my mind.
There’s a secret medieval communication system that will whisk your words above the noise of the crowd.
It’s in the courtyard of a building near the Duomo.
You stand at one corner and whisper into the wall, and someone standing diagonally across the courtyard can hear you perfectly.
No joke.
I tested it with a random guy who was visiting from Germany, and we both cracked up when it actually worked.
It’s a tiny moment, but it’s one of those hidden gems that makes you fall a little more in love with Milan.
Check Out The Igloo Houses In Maggiolina
In Via Lepanto, in the Maggiolina district, you’ll find Milan’s most unusual residential experiments—the igloo houses designed by engineer Mario Cavallè.
These dome-shaped houses were built after World War II as temporary housing.
Most have been renovated, but a few still have that original quirky shape.
They’re super photogenic and totally unexpected.
I took the metro out there just to see them, and it was worth the trip.
It’s one of those off-the-beaten-path spots that reminds you Milan’s full of surprises.
