Our day started with a 9:15 a.m. Last Supper ticket and walking tour with Wander in Italy. We arrived early and grabbed coffee and croissants from a nearby spot, Caffè Le Grazie, which had a suspiciously low rating—something like 3.4. I’m calling nonsense. The coffee was excellent, the pastries were excellent, and I’m convinced the low score was driven by American Karens expecting bottomless drip coffee and smiling waitstaff checking in every two minutes. Italian bars are efficient. They are not here to emotionally support you.

At the meeting point, there were several tour groups milling around, but our guide wasn’t holding a sign, so we had to guess. I spotted one gaggle that looked predominantly white, wealthy, and vaguely lost, pointed, and said, “That looks like our people.” And… it was.

Before going in, our guide gave us a lot of backstory on Leonardo da Vinci and why he painted The Last Supper here, because honestly we were all wondering. Of all places, why this fairly humble monastery dining hall and not somewhere flashy like the Vatican? Turns out it was commissioned in the 1490s by Ludovico Sforza as part of his big ambitions for Milan and the church of Santa Maria delle Grazie, where he planned a family burial site.

And Leonardo had deep ties to Milan. This wasn’t some random side project. He spent years there under Sforza’s patronage doing everything from painting to engineering to designing elaborate productions, because apparently one career wasn’t enough. He was even given living and workshop space near the church, which explains why such a world-famous work ended up in what is, at first glance, a surprisingly humble setting.

Then there’s the painting itself.

It’s super protected. You go through multiple sealed doors for climate control like you’re entering an art bunker. Temperature regulated, humidity regulated, visitor numbers tightly controlled, limited time inside. No lingering. No hanging around. Just you and genius for about fifteen minutes.

Access is so restricted partly because Leonardo, being Leonardo, experimented instead of using true fresco technique… and the painting started deteriorating almost immediately. Innovative genius, questionable medium.

And yes—tickets are always sold out.

Now I know why.

Tour companies scoop them up the moment they go on sale, mark them up, then add a walking tour of Milan afterward so you feel like you’re getting your money’s worth. Which, to be fair, we did.

Seeing it in person is strange because it’s so familiar you feel like you’ve already seen it a hundred times… until you haven’t. It’s enormous—much bigger than I imagined. And what struck me most wasn’t just the scale but the emotion. The moment depicted is when Jesus says one of them will betray him, and everyone reacts differently—shock, denial, suspicion, offense.

And somehow it survives. Through bad restorations, Napoleonic soldiers using the room like a barracks, wartime bombing that wrecked much of the convent but spared the wall, and centuries of humidity. Wild.

Also, random but interesting: Leonardo eventually left Italy and spent his final years in France because that’s where the power was. So yes… a bit of a sellout. But a brilliant one.

The walking tour afterward was a lot of fun, and I’m always down for urban wandering.

Our guide said something that stuck with me: “In Rome, beauty is everywhere—just look around. In Milan, you have to open a door.” What he meant was Rome wears its history out in the open—ancient ruins, fountains, churches, beauty just spilling into the street. Milan, by comparison, is more modern and wasn’t built the same way, so some of its charm is tucked behind courtyards, old doorways, and hidden spaces you’d never notice on your own.

But I also couldn’t help thinking… Milanese are very good at marketing whatever shortcomings they may have.

So maybe they’re not the obvious champions of carbonara, giant Tuscan steaks, or seafood… and they said, fine, risotto is our thing. And to their credit? They sold it. Hard. Saffron, tradition, signature dish, civic pride. Full campaign. Do I like it? Yes. But don’t hate me… it’s still rice. Fancy rice. Great job marketing it.

And once I noticed it, I started seeing it everywhere. Fashion capital? Incredible branding. Yes, people dress well—but they’ve also managed to turn looking expensive into an entire global identity. Then there’s aperitivo. At some point they basically took pre-dinner snacking and marketed it into a lifestyle.

Even “you have to open a door” felt a little like Milanese PR. Because another way to say that might be, we don’t have Rome-level beauty out in the open. But no—Milan says, our beauty is hidden, exclusive, curated. See? That’s branding.

It’s like wherever Milan may come up short, they don’t defend it—they repackage it. They elevate it. They make it chic.

Rome says, “Look at me.”
Milan says, “You have to know where to look.”

Not my style, but respect.

After the tour, we went back to our tried-and-true All’Antico Vinaio for some sammiches. Are we in Milan? Yes. Is it a Florentine sandwich shop? Also yes. Did we leave part of our hearts in Tuscany? Perhaps. We were very happy with our decision.

Also, thanks to being chewed up by mosquitoes, we stopped by a pharmacy to get some cream. Ahead of us in line were two Egyptian guys in their twenties, constantly cracking jokes. The pharmacist was a middle-aged Italian woman with blonde highlights, and I overheard the guys in Arabic making comments about her beauty, saying she must have fallen from heaven. It was highly entertaining.

They were using English as their shared—but secondary—language, which led to some amusing misunderstandings. The chubby Egyptian asked if she had any peptides, and she showed him a facial serum, explaining it was very expensive—€144—but would last six months. He was clearly looking for the weight-loss injections, but then he grabbed his cheek and asked if it would help with this.

I nearly lost it.

They started joking that the serum cost as much as the money they brought to Milan in the first place. At one point one of them turned around, made eye contact with me, and I think realized I understood everything they were saying. He slapped his hand over his mouth, laughed, apologized, and stepped aside to let us talk to the pharmacist.

It was a whole mini performance.

The rest of the afternoon was more wandering, shopping, aperitivo, and people-watching—which in Milan is practically a cultural activity of its own. Aperitivo had me a little delirious, and we opted to take a power nap before hitting the streets again.

Side note: we have bought more stuff in Milan than in any other city. Like I said… marketing.

The good news is that I intentionally let Matt pack his suitcase half-hazardly on the way here so that on our way home I can Marie Kondo-style pack it and fit all our new purchases. When I arranged his bag today with all of my new things, he looked at me like I had just performed a magic trick.

It’s what I do.

Dinner was at Ristorante Marino 1939 and somehow they ended up marketing starters, pasta, and a GIANT Florentine steak to us… and we bought it. Nobody even mentioned the risotto—it’s like they knew.

After dinner we headed west for gelato at Chocolat Milano, a place our guide recommended earlier in the day. Thankfully I pinned it as we were walking past it.

Now this is food Milan can and should be really proud of.