Milan: Ink, Off-Menu Carpaccio & the Night That Taught Us a Lesson
We arrived just after Fashion Week, slightly underdressed and completely jetlagged. Milan had plans for us anyway.
Milan was never supposed to be the destination — it was the launchpad. Two nights before the real journey began. But Milan has a way of becoming the story, whether you planned it that way or not. This is the post where we eat carpaccio that wasn’t on the menu, watch a tattoo artist work for eight hours, get sick from a glass of wine, and make a connection that would quietly save us five months later.
Read the series introduction for the full route overview and context. This post picks up on the morning of September 26th, when our Delta flight touched down at Milan Malpensa.
Arriving in Milan
The walk from Centrale — Milan at street level
We flew overnight from Orlando, connecting through Amsterdam, and landed at Malpensa in the late morning. After a long flight, we always prefer to walk when we can — it clears the jetlag cobwebs and puts you on the ground level of a city before the hotel room seduces you into a four-hour nap. We took the bus to Milano Centrale and walked from there to the hotel, stopping at a small café along the way. I had my first genuinely authentic Italian carbonara — the real kind, no cream, just egg and guanciale and Pecorino Romano — and it recalibrated everything I thought I knew about the dish.
(Note for next time: there is a tram that connects Centrale to the Diana Majestic. We discovered this on day two. Walk it once, then take the tram.)
The Sheraton Diana Majestic
First drinks in the garden — the trip finally begins
The Sheraton Diana Majestic on Viale Piave was exactly the kind of hotel Milan deserves to have more of. The old-world facade was striking — you felt the history of the building before you stepped inside. The lobby had that particular European hotel quality where the architecture does most of the heavy lifting and everything else simply tries not to get in the way. The hotel closed in 2025 after more than a century. We’re glad we were there when we were. Travellers looking for a similar old-world feel in the same neighborhood should look at the Westin Palace Milan on Piazza della Repubblica — a short walk away and cut from the same cloth.
We arrived knowing that Fashion Week had just wrapped up the week prior. What we hadn’t anticipated was that most of the designers, editors, journalists and assorted fashion world periphery don’t leave immediately — they linger. This meant the hotel was still very much in Fashion Week mode: limited room availability (no suites, unfortunately), a lobby full of people who dress for Tuesday the way I dress for a wedding, and an ambient energy of effortless chic that made me very aware of my Florida wardrobe choices. The warmth of the staff, though, made that self-consciousness evaporate almost immediately. They were genuinely gracious.
The Porta Venezia neighborhood sits near the Metro and several tram lines, with bars and cafes within a short walk in every direction. It’s a genuine neighborhood, not just a hotel strip — and a far quieter base than the blocks immediately surrounding the Duomo. Give yourself time to explore on foot in the evenings.
Day One: The Garden, the Artist & the Night That Taught Us a Lesson
After settling in we did what the hotel garden demands of you: ordered cold beers and snacks and sat outside doing nothing productive for a while. After a transatlantic flight, this is not laziness — it is strategy. Tucked behind the building, quiet and lush — a proper garden, not just a patio with some chairs — it had a way of slowly returning you to yourself.
Mauricio had arranged a consultation with a local tattoo artist before we left home — something he specifically wanted to do in Milan, a way of carrying a piece of a place permanently. After the garden, we walked the four or so blocks to the studio to meet him and discuss the work.
The artist gave us something immediately valuable beyond the consultation: a tip about a small street nearby decorated entirely with murals, hidden in plain sight away from the tourist circuit.
Panino Giusto & the Off-Menu Carpaccio
The mural building facade of Casa Galimberti
We found Casa Galimberit exactly where he said it would be. On ground level was Panino Giusto — a sandwich chain with beautiful mural-covered exterior walls and outdoor tables spilling onto a quiet corner. We had not planned to eat there. We just sat down.
Carpaccio is not on the menu at a sandwich shop. We know this. But we operate on a simple travel principle: ask for what you want and see what happens. The worst answer is no. So we asked our waiter whether it would be possible to put together a carpaccio. He looked at us with the expression of someone who has been asked an unusual question and has already decided the answer. “But of course!” he said.
What arrived was outstanding. The beef paper-thin, the Parmesan perfectly shaved, the olive oil bright and grassy the way it only truly is in Italy. Fresh ground pepper, crostini alongside. For something that did not exist on the menu twenty minutes earlier, it was flawless.
“Never be afraid to order something that is not on the menu. The worst they can say is no — and in Milan, they rarely do.”
Panino Giusto, Milan — September 2019The Night That Made Us Paranoid About Wine
We continued walking the neighborhood after dinner, stopping at a few bars along the way. What followed was one of those evenings that can only happen when you have no particular plan and nowhere to be. Groups of young Italians kept pulling us in — a table outside a wine bar where someone had overheard us debating which direction to walk and simply said sit, sit — another hour at a standing bar where a group of students wanted to know everything about our story and told us everything about theirs in return. The kind of conversations that start with a gesture and end two hours later when someone realizes it is past midnight. It is the thing about Italy that no itinerary can manufacture: the willingness of strangers to make you temporarily theirs.
It was also on this same bar-hop that two experiences permanently changed how we handle drinks in unfamiliar places.
At one outdoor table, Mauricio went inside to cancel our order — after waiting almost 10 mintues, we had decided to move on. He found the server pouring leftover wine from used glasses into fresh glasses for new orders. The same with beer. She saw him and said something to the effect of “They are almost ready.” We left immediately. What he witnessed is known in the industry as “slops” — recycling unfinished drinks back into service. It is illegal under most health codes and universally kept from customers for obvious reasons. New rule for the rest of the trip: watch your drink being poured, or order bottled beer. Later that same evening I ordered a glass of wine at a small bar at the end of an alley. After one sip I knew something was wrong. I asked Mauricio to try it; he got it near his face and told me not to drink it. It smelled like rubbing alcohol. After just that one sip, I was violently ill when we got back to the hotel.
This is not a Milan problem — it can happen anywhere. But it happened here, on our first night out, and the lesson stuck: watch the pour, order bottles when in doubt, and trust your instincts if something tastes wrong. One sip is already too many.
One more thing worth noting: bars that cater primarily to locals have far less incentive to cut corners this way. When your regulars come back every night, your reputation is everything. Tourist-heavy areas — especially those near major landmarks or in high foot-traffic corridors — attract a transient crowd that will never return regardless. That anonymity is exactly what makes shortcuts like this possible. When in doubt, follow the locals.
Day Two: Ink & Authentic Milan
When we woke the next morning, we were ready to see the side of Milan that doesn’t come in a glass — but first, I needed to actually recover. While I spent more hours horizontal, waiting for the room to stop spinning, Mauricio headed back to the studio early. He spent the entire day in the chair getting the Biscione — the great Visconti serpent that has been the symbol of Milan for nearly a thousand years — along with a rework of an existing piece. Eight hours of work. I joined him in the afternoon, once I was able to get up, shower, and eat a proper breakfast.
Eight hours in the chair
The finished Biscione
What I found when I arrived was one of those unscripted afternoons that no guidebook can give you. The studio was filled with authentic Milanese — the artists, their friends, people dropping in. I sat and watched the work, listened to conversations I could only partially follow, and felt genuinely inside the city in a way that the Duomo piazza never quite delivers.
It so happened that the famous Italian rapper, Vacca, was getting some work done as well. Covered almost entirely in tattoos, he can be an intimidating figure, but I found him personable and genuine. He had a playful sense of humor and a real curiosity about why Mauricio had chosen that specific image. The day was unhurried, warm and full of laughter; to this day, Vacca’s music still makes its way through my playlist.
The artist became a contact we kept after the trip. In early March 2020 — months after we had come home — he sent us a message. Covid was moving through Milan faster than anyone was publicly acknowledging. At the time he hoped the quarantine would last until the end of the month. He told us exactly what was happening, what he was seeing on the streets, and how to prepare. We were among the first people in our circle to take it seriously. That afternoon in his studio turned out to be one of the most consequential things that happened on the entire trip.
The Biscione — Symbol of Milan
The serpent devouring a child (or, in some interpretations, giving birth to one) has appeared on Milanese heraldry since the 12th century — the symbol of the Visconti dynasty, still seen on the city crest, on Alfa Romeo cars, and on Inter Milan’s badge. Mauricio now carries it permanently.
A Postscript — Three Years Later at JFK
In 2022, we were sitting at a bar in JFK waiting to board our flight back to Milan — this time en route to Venice. A young Italian man sat down next to me. When Mauricio got up, he leaned over. “I have to ask,” he said. “Where did your husband get that tattoo?”
I told him: Milan, 2019, a small studio near the mural street. He shook his head slowly, a look of genuine disbelief on his face. “You won’t believe this,” he said. “My brother and I have the same one. We each have half — I have the serpent, he has the shield and the child. It is our family coat of arms.”
JFK, 2022 — two strangers, one serpent
The Biscione atop Villa Olmo — Lake Como, days later
We talked until time to board, all of us going to Milan but on different planes. Of all the barstools in all the airports in all the world, two strangers connected by a thousand-year-old serpent found themselves together at JFK. Whether you were born into it or felt compelled to have it etched into your skin — or both! — Milan has a way of imprinting on you in ways you never expect. Sometimes, years later and thousands of miles from the Viale Piave, it finds a way to remind you that you’re still part of the story.
The Duomo, the Galleria & the Rooftop That Changed Lunch
On our final morning in Milan — day three, with our afternoon train to Como already booked — we had plenty of time for the city’s marquee sights.
We took the Metro to Piazza della Scala, then walked toward the Duomo di Milano. We caught our first glimpse over a block away; even at that distance, it was breathtaking. Neither of us is drawn to standing in queues to crane our necks around dozens of others just to see interiors we’ve already seen in photographs — we’d rather spend that hour exploring the city on foot. The Duomo, viewed from the piazza, is extraordinary enough on its own. A giant, towering cathedral that took over 600 years to complete, it is one of the largest in the world. With its imposing facade, it defies a single classification, wearing a blend of styles that were in vogue across the centuries of its construction. True to the spirit of Milan, it remains a mix of style, mystery, and a strange bit of familiarity.
Also on the Piazza della Scala, the Galleria Vittorio Emanuele II is genuinely magnificent — and genuinely packed. The crowds are dense and constant; this is one of the most photographed interiors in Italy and it shows. Push through anyway, because the architecture earns it. The floor has four mosaic roundels representing the coats of arms of the original unified Italian cities — Turin’s bull, Florence’s lily, Rome’s she-wolf, and Milan’s Biscione. Everyone knows about the bull. Almost no one stops to find the she-wolf roundel alongside it: the ancient lupa nursing two young, right there underfoot. Look for it before you spin. Then spin on the bull — the tradition holds that standing on its most sensitive anatomy and turning three times brings good luck. The mosaic is worn completely through at that spot. Either it works, or there are a very great many optimistic tourists in Milan.
The Duomo from our lunch table — La Rinascente rooftop
Then came the tip that made the morning: lunch at La Rinascente, the department store on the piazza. The top floor restaurant looks directly at the upper facade of the Duomo — close enough that you feel you could reach out and touch the marble. Most people walk past this building a hundred times without looking up past the ground floor windows. We had a proper lunch, cold drinks, and one of the best views in Milan, without a queue, without a booking, and without spending a fortune.
We packed our things, took the tram to Centrale this time (lesson learned), and caught our afternoon train south toward the lake.
La Rinascente’s rooftop restaurant on Piazza del Duomo offers arguably the best close-up view of the cathedral’s upper facade without climbing it. No reservation required for lunch. Order a Campari spritz and take your time.
The Train to Lake Como
The Milan to Como run is just under an hour on the regional train — a short, easy hop that barely registers as a journey. But it marks a profound shift. As the urban sprawl of Milan’s outskirts gives way to the first glimpses of deep blue water and rising mountains, the city falls away. The air feels different. The lake appears, and the pace of the trip changes entirely.
We had deliberately booked a later afternoon departure to give ourselves a full final day in Milan. It was the right call. When we pulled into the small station, the afternoon was fading into evening and we decided not to risk walking the 45 minutes along the lakeside after dark — with suitcases in tow. We grabbed a taxi for the short drive to the hotel. We arrived at the Sheraton Lake Como with the light still golden on the water, ready for a different kind of Italian magic.
Next Stop: Lake Como
The train from Milan takes just under an hour. The lake appears and everything slows down. Part 2 is coming soon.
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