[MILAN, ITALY] — When I was going to school in Rome, I was obsessed with Old Things. We zoomed all over Europe every weekend, compartments loaded up with beer, on our unlimited Eurail Pass looking for cool old stuff.

The only thing I knew about Milan was our midnight stop at the train station, jolted awake from a drunk sleep each time by the same old man hawker each time, with a raspy smoker’s voice outside our drawn shades: “Birrrrrra. Acqua Mineraaaaale. Chocccolaaato. Orangiiiiiina. Aranciatttt-a. Coca Cooolaaaa.” repeated over and over until the train departed. Then again the next time we flew through. Anyone who passed by Milano Centrale in the 80s knew that voice.

When someone would ask “Should we go to Milan?” “Why? There’s nothing old there, it’s just a city.” (okay, this was 1981). “I hear the Duomo is cool, but that’s about it.” “I’ve seen enough churches.”

Boy were we wrong. I’m a grownup now.

Milan and Italy have certainly changed since 1981. People aren’t wearing the same suit pants and dress shoes as their parents everyday, even to the beach. Everyone is hipper, with tatts and shorts and hip trainers — a global look that would fit in in Brooklyn or Paris or London — and Milan has become the Soul Center of the Universe.

Cool stuff flows from Milan on my daily Instagram sessions, great design, amazing looking restaurants, funky furniture and cool clothes. Annual design and fashion shows popping regularly from peope I follow on Instagram. Amazing things, all the time.

So when we had a chance to spend a long weekend heading to the Dolomites, I was giddy. I’ve since been back a couple more times, often just overnight, but vowing to come back longer, if not move there. These are all the cool things I found over a long weekend. I know for certain there’s a ton more, I can’t wait to come back. I’ll keep updating this post.

Get Blown Away By The Duomo

I had no idea what I was in for. I’d seen hundreds of pics of the Duomo in Milan, but nothing prepared me for how amazing it was inside this cool, dark stone forest. More vertical than broad, standing between the columns they look like a pointed laser into the night sky, high into infinity. Check out this stone forest:

There are 40 of those giant columns and they’re 8 stories high! It took six hundred years to complete the Duomo, starting in the late 1300s. They even have an augmented reality tour you can take that shows how everything looked over the years.

It’s the largest cathedral in Italy — St Peter’s is actually in the Vatican state. This plot used to be the main Roman temple across the forum, so all roads in Milano lead to the Duomo, standing up proud at the center of the entire city. Check out this crazy Google page on the Duomo.

There are 40 of those giant columns and they’re 8 stories high! It took six hundred years to complete the Duomo, starting in the late 1300s.

I was so blown away, that I ducked back in the Duomo every time we were even close. Don’t go just once. Especially if it’s cloudy and dreary, go back as soon as the sun comes out.

We had a lot to do for our short time, so never got a chance to get up on the roof, but I recommend you do so or you can do it virtually here. Reserve online beforehand at the official Duomo site.

Check Out The Cool Solar Clock

This is so cool. I love me some sundially stuff. As soon as you walk into the Duomo, look for this beautiful tile and the brass line that runs through it. This is a solar clock and calendar, designed in 1789. Look up to spot a hole in the ceiling, that’s called a gnomon, which is where the sun peeps in and shines on the floor, indicating when it is Noon, moving throughout the seasons. Astrology signs on either side help track the month. Once it hits noon, they signaled to a castle down the street and who shot off a canon to let everyone know it was noon, then everyone was able to be on the same time. And thusly, the same songsheet. 😜

You can check out the animated version on Google’s cool Duomo site.

Walk Every Street of Brera — My Favorite Neighborhood

There are so many cool streets in Milan. It’s such a clean city, especially compared to Rome. We were zooming all over and I’m kicking myself for not taking more pics of the wide stone-paved boulevards with quaint trams quietly zooming by.

But one neighborhood I loved the most was the ultra-posh Brera district. So many amazing apartment buildings, flower-lined balconies, outdoor cafes and upscale shops. This is where the cool people live. Just go and zigzag, block by block. Then go back again.

Bottom photos from TripAdvisor

Here’s a fantastic guide to Brera from the always amazing Italy Segreta. Here’s Culture Trip’s Guide to Brera. and TripAdvisor’s guide to Brera.

Cool Off Seeing The Famous Fresco

For years of art classes — starting when the Picture Lady would show up in our grade school, through high school, then art history classes in college — every time the photos of DaVinci’s Last Supper always had the top of a door in every shot. Like a finger in your family selfie.

Then they explained that is was an old door, but still didn’t make much sense to a young brain. But once you see it in person, you get it. And a lot of other things.

I wasn’t that excited about seeing The Last Supper, but it was way more impressive than I was expecting, especially the very cool church, Santa Maria delle Grazie, it is part of. It’s a very small room, much smaller than you’d think. Thankfully, they limit the times you’re in the room and you need to book in advance (here), but that makes it completely different, more private and subdued experience, than seeing, say the Mona Lisa in The Louvre. Be prompt, there are narrow windows of time you’re allowed in there.

Have an Aperol Spritz In The Galleria Vittorio Emanuele

This has been the center of high fashion and elegance in Milan for centuries. A great glass enclosed shopping arcade, directly across from the Duomo. Some of Milan’s older luxury stores are here, so you can pick up a hat at classic places like Borsalino. Or look for the signs and go up on the Aperol Terrazza and have a spritz while you overlook all the people below. Here’s an article about drinking a spritz here in the Washington Post and on Trip Advisor.

Conveniently located right across from the Duomo, the Galleria Vittorio Emmanuale has some of the highest end shops in Milan. It’s an architectural marvel, as it has been for hundreds of year.

It gets busy, but surprisingly not in a claustrophobic way, play these little video snippets:

Hit The Happening Navigli District

I never knew Milan had a canal district, it used to have concentric rings of them, like Amsterdam, but most of them have been covered over. Some of the canals go back before the Romans, to the Celts who built them. They did such a good job that the Romans didn’t have to build aqueducts to feed their thirst for water.

But today, the canals in the Navigli District are still there and thriving. I had no idea Milan looked like this. These used to be all industrial canals, polluted and full of dead horses, but they’ve really been cleaned up in the last decades. Now, loads of restaurants, shops and apartments are spread all over. The area feels like Östermalm in Stockholm or Canal Saint-Martin in Paris, with a bunch of intersecting canals, lined with restaurants and bars and thousands of roving people.

It gets a little busy at night. Here’s Time Out’s guide to the Navigli and here’s TripAdvisor’s.

You Should Eat Here In Milan

Feast Your Eyes at Da Giacamo

A remember seeing the first pics of da Giacomo in this article in the New York Times magazine and drooled. The most subtle mottled-green wainscoting, frilled in the center, surround by the richest ocher walls. I tore it out and stuck it in my Milan file.

Soon after the Style magazine article, my good friend Pete Marczyk — a god of good taste and famous gourmet grocer of Denver — texted me a photo of the exact same place as in the article. He and his wife Barb were able to sneak in on a food buying trip in Milan. That’s when I knew that’s the #1 place I had to go to as soon as I got to Milano.

So I was able to get an early table and drag my friends with me. We’re silly Americans, so an early reservation was no problem. Early, like 7pm. When we got there we were the only people in the room, the staff busily prepping in the back for a full evening. At first, the service was brusk, but the nice waiter soon realized we were not the typical Americans trying to eat quick and go. He warmed up, got what we were after and made for a perfect evening.

As our dinner wore on, the place started to fill up quickly. Not with busloads of tourists, but elegant Milanese. The people-watching was off the charts. We were there all night.

Da Giacomo’s specialty is seafood. Get it. All of it. Whatever the nice men recommend, say “Si! Per favore.”

Da Giacomo is on everybody’s Top 10 best lists in Milan… and some in all of Italy. It is such an incredible space, try booking before you head to Milano. Or if you can’t, check out some of their other cool restaurants. They all look amazing.

Have a Blast Waiting for AM Pizza

After such a great meal at da Giacomo and walking all over Milan the next day, we decided to eat something easy. My best friend’s son Mark, and therefore my best friend, googled popular restaurants near our Airbnb. “Hey, there’s a pizza place that’s supposed to be good not far from here.”

Pizza AM, my god this was such a great experience, when we got there, there was a ton of people out on the sidewalk drinking out champagne glasses and chatting away in Italian. My first thought: “oh this is going to be a nightmare. I don’t really want to wait.”

But right then, the door opened with a gaggle of loud Italian voices and music streaming out. A trim nice man holding glasses and bottle of prosecco said “Are you here for dinner? How many are you?” then promptly started passing out glasses to our group and pouring “What is your name? Don’t worry, it won’t be too long, I come find you.”

Fantastic. We stood out on the skinny sidewalk, smiling. The neon sign above our heads flickered and spelled out P-I-Z-Z-A. It was no time before we were shuttled in to the back room. The noise was a roar, the music blaring, the animated Italian conversation flowing at every table. It was fantastic, from the waiting until the after-dinner drinks at the end. Here are the Top 10 pizzas in Milan in TimeOut, which Pizza AM is one of them. Click on these video snippets and you’ll feel like you are there:

Go Prowl The Navigli District

I don’t remember where we ate here, but it was good. Dozens and dozens of places, from simple to fancy. Do what we did and just walk around until you see something good. My golden rule : You can always tell what’s good by their patio furniture™️.

Get a Cappuccino at Un Posto a Milano

This place is just such a lovely vibe. A 1800s abandoned farmstread, right in the middle Milan, restored to be a culinary cultural center, with an amazing coffeeshop, very nice restaurant, a bookstore, a demonstration garden to teach kids about growing food, even a hostel upstairs. It’s so cool, I did a whole post about it, here. You can come for a cappucino, lunch, an aperitivo or a nice dinner in the old schoolhouse.

Where Others Recommend to Eat

Here is the NY Times article on a chef’s guide to eating in Milan. And here is the NY Times T Magazine guide on where to eat in Milan.

And here are recommended top spots in Milano by people I follow and respect on Instagram. You can scroll and see what each place looks like and the names should be in the bottom of each:

You Should Stay Here In Milan

The Aethos

When I stayed here, twice, several years ago, this hotel was called The Yard. It was built in a wide open space that used to be an auto repair shop. The entrance was nondescript from the street and you walked down an alley to find the entrance.

They’ve since changed their name to Aethos, but still owned by the same family. And the place feels like it is family-run. They’ve done some major renovations, particularly in the rooms, but the vibe and feel remains the same. Check out their website to see the latest look. I can’t wait to come back.

The whole place was just such a trip. Totally genuine. Totally unique. And not what you’d expect when you hear the words “Hotel in Milano”.  You should stay here. Or stop by for a drink. And you can’t beat the location, walkable to most everything. 

It looks like they’ve really amped up the place, with a full-on restaurant, happenings and more. 

The Aethos is a collector’s paradise, with an insane collection of antique car and sporting things, collected over the years by the hotel’s owner. It’s like a funkified Ralph Lauren collection. With a ginormous outdoor bar/gathering area, with huge tables, big comfy couches and oodles of things to stare at in wonder. And an excellent cocktail bar, complete with suited and bearded mixologists, perfect for enjoying a ‪negroni‬ or other fine crafts away from the flow of people on the outside.

Every room has a different design theme and related antiques. The finish levels are some of the finest I’ve seen, with plenty of room and awesome bathrooms. I stayed there twice, coming and going from the Dolomites, staying in a different room each time.

But the best part? (and you’ll read a lot about it in all the reviews) The breakfast. Just perfect.

They’ve redecorated and renamed the hotel from when I was there, the rooms are much different, friendlier and not as moody, but they remain as big as always. It looks like they’ve kept much of the common areas the same and have really upped the restaurant and special events to maximize this cool old auto repair shop.

More Information on Milan

Here’s a great article on all the cool things to do in Milano from my fave issimo.com fashion website. Here’s the NYTimes 36 hours in Milan guide. And an older version. Here’s TimeOut’s Guide on the Top things to do in Milan. Here’s Goop’s guide to Milan. And a Design Lover’s Guide to Milan from Conde Nast Traveler. Here’s NY Times T Magazine guide to Milan by famous people. Here’s Travel & Leisure’s guide to Milan. And AFAR’s guide to Milan.

And for the UK perspective, Conde Nast Traveller’s guide to Milan. And The Telegraph’s guide to Milan.

Here’s a post I made about two great day trips from Milan.