Best Cities in Italy: Milan

From the back of a Milanese taxicab,

the city’s skyscrapers are enchanting;

from close up, they’re overwhelming.

Sleek, artistic, & ultra-modern,

the city’s luminous buildings are a symbol of its newness.

When you contrast them with the city’s classical charm, you have the

dynamic interplay of a drama that’s worth documenting.

Here’s how my journey to Milan— Northern Italy’s masterwork —

unfolded this past summer.

But first an introduction of the city by way of contrast.

Milan vs. Rome & Florence

While I’m reluctant to call any grouping of major Italian cities that

excludes Naples a “Big 3,” Rome, Florence, & Milan could definitely fit this description (from the P.O.V. of an American tourist at least ).

Here’s how the latter stacks up:

If Florence takes the prize for most overall artwork, Milan keeps pace, thanks to the pre-eminence of the artists and pieces it houses (DaVinci’s Last Supper being the primary example).

With a skyline reminiscent of any American metropolis, Milan is also much more modern than Florence or Rome.

Finally, its status as one of the world’s most important fashion cities make it a must-experience destination. So I packed my bags to experience it…    

With Milan firmly penciled in as the first stop of my ’17 Italo-trip, I knew that it would be one to remember.

The wildcard?

My Uncle would be accompanying me.

With his off-kilter, unpredictable personality and our past vacation history

(that included riding aluminum bikes in the middle

of an Italian lightning storm

it promised to be a vacation to remember.

Here’s how it played out.

Persistence, Best Western Deskmen,

& “Seeing” The Last Supper

Aldo (a native Italian who emigrated to the U.S. as a kid) and I had been craving this Italo-trip; it had been 10 years since he’d last seen the homeland (7 for me). The primary topic of our exhaustive pre-trip planning efforts?

Mainly how much food we were going to eat… 

but also the opportunity it  would provide us to soak in so much old-world culture.

Part of this, of course, included DaVinci’s Last Supper, that my Uncle was now adamant that we see.

I was fairly certain that we needed a reservation to pull this off— a fact confirmed by the deskman of the Best Western we were staying at— but my Uncle was resolute that they’d somehow make an exception for us.

(Off-kilter personality, remember?)

When you combine that with a heavy dose of determination, off we went…

After a taxi ride that involved the driver relating the intricacies of his

trade (ad nauseum) and then refusing to accept a tip because he had already taken us the longest way possible to jack up his fare, we were at the

Santa Maria delle Grazie church.

It took 2 minutes for us to find out we wouldn’t be seeing DaVinci’s


No shock there.

The usher was quite adamant that people booked viewings in small groups months in advance and since we hadn’t…

“Well, let’s just walk around a bit,” my Uncle quipped with a gleam in his eye.

He’s not giving up, I could hear myself mouth.

After a trip through the church’s hallowed halls in an attempt to find the room that housed The Last Supper, he finally acknowledged that we might be out of luck.

So we exited quietly.

While we’re walking off, a middle-aged Italian man loitering behind the gate in the church side of the courtyard catches my Uncle’s eye.

I groan.

Here we go.

He elbows me: “Hey, how come he gets to be back there?” and off he goes to ask him.

“They told us we need a reservation; is that really true?” he asks the man in Neapolitan-style Italian.

The man confirms it, adding that The Last Supper isn’t even on display today anyway.

Then comes the inevitable:

“Hey, how come you get to be back there? Are you sure you’re not

waiting to see The Last Supper?”

“How come I’m back here?”


“I live here.” 

Dumbfounded by the inane answer, we hail a taxi for our next

(inevitable) misadventure.

From the Back of a Milanese Taxicab: New Milan

From the back of a Milanese taxicab the skyscrapers passing by are so damn charming.

Each one tells its own story.

Olive hues, slick geometry, & refracting light attract the eye.

Novel color scheme upon novel color scheme hits me.

There’s even towers boasting full-on gardens complete with over-sized trees.

New Milan is out in full force.

I’ve never seen anything like it.

I don’t miss home.

Culinary Interlude

“E buona questa Milanese!”

My Uncle is engrossed in his fried veal dinner— or Milanese — the city’s signature dish. In fact, the cut is larger than his head and by his frequent exclamations, I can tell that he’s made the right choice.

The waiter leans in, his tie jam-packed with Disney characters like a cheerful Pluto, to top our glasses off with sparkling water.

Seeing the wacky conversation piece, Aldo dives in.

He points out each character as he slowly recites their names one by one—“Mickey, Pluto”— while the waiter nods his head in approval, a big smile plastered across his eager face.

Seeing that his outfit’s centerpiece is receiving the attention he so clearly had hoped for when he put it on, he can hardly contain himself.

He’s beaming as he answers questions about the menu, the city, country, and who-knows-what-else.

The Disney waiter’s  answers are delivered in such an affected, theatrical manner that his performance would make any opera-lover proud.

*He’s a classic Italian conversationalist, just like my Uncle*

The two wrap up their impromptu Q & A  and shake hands as the waiter walks off.

My Uncle downs his glass of vino that seems to have materialized out of nowhere, shakes his head, and turns to me: “Out of all the cartoons on his tie, that guy was the biggest character of them all!”

Old Milan: Castle Sforszesco

“Hakuna matata.” 

The hits keep coming.

I’m walking through the courtyard of the historic Castle Sforszesco looking for the Michelangelo exhibit.

Built in the 14th century, the pale reddish castle houses an exquisite art collection, including  an armchair created around the sensations Mendini felt while reading Proust novels.

This time I’m without Aldo because he’s hitting the street vendors to barter for a new rolling suitcase (one of the wheels from his first one snapped off five minutes after he got off the plane from New York).

It’s a hot day and I’m disoriented from all the running around.

“Hey! Hakuna matata man.”

I whirl around to a smiling 6’5-ish African immigrant who puts his hand in mine for a hip-hop handshake.

He’s smiling like we’re long-lost friends.

His out-of-the-blue charm is so intriguing that I answer the greeting with a (cautious) “hakuna matata” of my own.

As I go to pull back my hand he places a holder with a friendship bracelet on my wrist, ties it expertly, snips the bottom with an over-sized pair of scissors, and then quickly pulls the holder away, tossing it into his bag in one fluid motion.

Clearly, he’s done this before.

I’m dumbfounded as I stare at the multi-colored decoration hanging on my wrist.

What just happened?

“Give a donation, man.”

Oh ok, now I see his angle…

but since my new friend’s approach was so original I can’t help but toss him a 5 Euro piece.

As I walk off in search of the Michelangelo exhibit I’ve heard so much about, another immigrant approaches me— this time flat out asking for money.

How to respond?

“Ask your friend, he has it all” I say, nodding to The Lion King enthusiast.

The Showstopper: Galleria Vittorio Emanuele II

Fresh off our series of comic misadventures we’re feeling loose and ready for shopping. As it turns out, we happen to have one of the world’s most

luxurious shopping malls a few short miles from our hotel: Galleria Vittorio Emanuele II.

Its entire structure could pass for a work of art.

There’s arched ceilings made of glass as far as the eye can see and the mosaic floor is mesmerizing.

To me, it’s Rodeo Drive crammed into one beautifully decadent, 

spacious outdoor shopping concept.

Prada, Versace, Rolex, they’re all here…

but it’s the last one that attracts my Uncle, so he wanders into the belly of the timepiece giant ready to make a deal.

After a quick 360-degree whirl around the disappointment shows on his face.

He looks the way I do when I call down for room service only to find out that the kitchen’s closed for the night.

“There’s nothing in green???”

“Afraid not, not in this store anyway” the wide-eyed saleswoman confirms.

“Ok never mind then; for me it’s green or nothing.”

We walk out in earnest.

“I only like Rolex’s that come in green,” he re-iterates, to no one in


As if the absence of his favorite color— and not the 5-figure price tag— was what made him hold off from buying.

        . . . . . . . . . . . . . . . . . . . . . . . . . . . 

Milan ended up being the perfect blend of old & new…

and while the rest of the trip was memorable, it couldn’t live up to the hi-jinx, high points, and head-scratching moments we experienced in our first city.

*Grazie Milano*

Note: credit for the feature image of the aerial shot of Milano goes to

Copyright: <a href=’′>florin1961 / 123RF Stock Photo</a>


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