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A Perfect Weekend in Milan: Travel Guide for Women

The prospect of a weekend in Milan made me curious, a bit nervous, even.

It is Italy’s fashion capital – and I am not particularly known for placing style over comfort.

Yes, I felt a bit of trepidation.

Milan travel guide for women - Montenapoleone streetMontenapoleone - street of high fashion

As the train pulled into Milano Centrale, I looked at the sky – dark, gray, a fog so dense it shielded the top floors of the scattered skyscrapers we passed. I hugged my umbrella tightly, wondering how I would spend the next 48 hours frizzing and freezing.

I had an initial list of things to see and do in Milan: Da Vinci’s Last Supper, for which I’d bought a ticket beforehand; the Galleria Vittorio Emanuele II, because I love patterned floors and cut glass ceilings (and – ceilings mean no rain); I planned to walk around Brera neighborhood to see street art; and I wanted to go to the top of the Duomo.

That was the plan. Now here’s how it turned out.

Milan travel guide for women - DuomoMilan's Duomo - as it would have looked on a sunny day

Having visited Milan as a child, I had vague memories of the Duomo soaring into the summer sky. Just like in the above photograph.

But the reality was more like... THIS.

Milan travel guide for women - Duomo in the fogDuomo in winter fog - still imposing

Rather than pay for a rooftop visit and see nothing but a few flying buttresses, I instead circled the Duomo Cathedral's exterior, taking in the carved stonework and massive doors and fighting off wet umbrellas, too cold to even consider the damp and dark interior.

What a wonder it is! So grand, so solemn, so vast! And yet so delicate, so airy, so graceful!  -Mark Twain

Some people despise its mishmash of styles, others love its majesty - but Italy's largest cathedral probably won't leave you unmoved. Every inch appears carved (because it is): the Duomo has 3400 statues, more than 130 gargoyles and hundreds of carvings. It is more decorated than any other building in the world.

Building started in the late 1300s in white and pink marble brought in along the canals, the navigli now lined with cafés and restaurants. For centuries, architects labored over the nave but even after it was consecrated, building continued on and off. The facade was finally completed by Napoleon, who wanted it for his coronation as King of Italy - which he created while he ruled France.

It's not even finished yet. Apparently there's still a bit of carving to be done...

As the rain sliced across me I decided to seek refuge in the Galleria, one of the world's oldest shopping malls. Although it has a giant glass and cast iron ceiling, its ends are open to the street so you’re inside, but outside. Shaped like a cross, each four-storeyed ‘avenue’ is lined with shops and cafés. I mean, who doesn’t want to sit and watch the well-dressed Milanese amble by?

Milan travel guide for women - Galleria Vittorio EmanueleThe ceiling of the Galleria Vittorio Emanuele II - one of Milan's most iconic sights

In all the excitement of looking up at the ceiling, I had somehow overlooked the bull’s balls.

One of the coats of arms etched into the floor belongs to the nearby city of Torino, which in Italian means little bull. According to legend, a man may have fallen to his death while building that glass ceiling – right where the bull is located. For some obscure reason, it is considered good luck to grind your heel into where the bull’s testicles should have been, and then twist around (backwards) three times. Given my motion sickness, I would have ended up on my face if I’d tried, but here’s what it looked like, more or less.

And now it was time to see Leonardo da Vinci's Last Supper.

A little backstory: the painting captures a single moment, when Jesus reveals someone at the table is about to betray him. Waves of emotion move across the apostles' faces... surprise, shock, anger. It is painted on the wall using a technique Leonardo invented specifically for this particular work of art. Sadly, the technique didn't work, the paint came off, and every effort to restore it made it worse.

It is a large painting and takes up the entire wall of the room that houses it, but it is incomplete since a doorway was built below it, cutting off part of the bottom, including Jesus's feet.

The miracle of the Last Supper is its survival. It was used for target practice by Napoleon's soldiers, and the building was bombed during World War II, yet the painting, protected by scaffolding and sandbags, made it through.

So I knew this would not be a pristine work of art, a perfect painting. On the contrary, I expected to see something old, perhaps even neglected. 

The painting is high on the wall, and relatively distant from the audience. These are necessary precautions, given the Last Supper’s fragility and the potential dampness of centuries-old walls.

The visit is highly organized – and rightly so. Thirty people are let in at a time, on schedule. The doors ahead open once everyone is in the room, keeping out the elements that are so dangerous to the painting’s survival.

But for me, it was hard to see. The (necessary) gloom of the refectory made the expressions of the faces difficult to discern, the folds of the clothing and the shapes of hands and feet fuzzy. I would have liked a few well-lit panels nearby to explain what I was seeing, so be forewarned - because you can do a lot better.

My first suggestion is to do plenty of research, knowing you won’t see things clearly once you’re there. Memorize the painting before you go, and know exactly what you're looking for. Second, hire a guide. A gentleman near me had done that but no matter how far I leaned over I couldn’t hear a thing. A guide will fill in the (many) blanks and answer your questions – trust me, you’ll have plenty. 

Milan travel guide for women - the Last SupperThe Last Supper by Leonardo da Vinci

I’m thrilled to have been in the same room with this treasure, and I could feel its mysteries and its power. But I could kick myself for not having prepared my visit better.

And so off I went to Brera to look for street art.

Here’s what I found instead.

Milan travel guide for women - antique shop in BreraThe streets of Brera are filled with stylish and original shops - like this little antique store

It is a cobblestoned neighborhood, filled with eclectic shops, a smattering of cafés, and dozens of pizzerias whose quality reflects the absolute certainty that you’re a tourist and will probably never be back. There are apparently a few excellent restaurants in the area – but I wasn’t to find them.

Nor was I to find street art.

Someone may have had fun with a translation and substituted street art for artists because yes, there were plenty of artisans, but any graffiti would have been instantly scrubbed off Brera's gentrified walls.

I did find street art, courtesy of a Milanese friend who guided me to a place I’d never heard of: the columns of San Lorenzo, a series of 16 impeccable Corinthian columns in front of the Basilica of the same name. I saw street art around a corner, and down another, but I know I barely scratched the surface, given Milan's fine artistic reputation.

The 16 San Lorenzo columns, right across from the Basilica of the same name

Suggestions for art of a different sort led me to the 16th century San Maurizio al Monastero Maggiore, which Milanese describe as a mini-Sistine Chapel.

The unprepossessing former church sits on the Corso Magenta, just down the street from the Last Supper. If you didn't know, you’d walk right past it.

Once through the doors, a small patio encloses disparate antiquities of Mediolanum, the Roman name for Milan – a frieze here, a column there, a bit thrown together but unexpectedly informative about the way life used to be around these parts and not surprising, given that the Archeological Museum is right next door.

The sky remained gray and gloomy, but the church was the perfect antidote to the winter outside.

Milan travel guide for women - San MaurizioThis is what you see in front of you when you enter San Maurizio
And this is what you see when you go behind the altar into what used to be a convent - and note the massive organ on the left

Top 5 Things to See in Milan, Italy

If I were to list my top five picks for a weekend in Milan, here's what they would be:

1.     San Maurizio - absolutely stunning and unexpected

2.     A walk around the Galleria Vittoria Emanuele II while admiring the gorgeous glass ceilings

3.     Walk around Brera and look into (or actually go into!) the many clothes and antique shops

4.     Visit the Last Supper (get your ticket ahead of time and READ UP!)

5.     Explore the street art and columns and basilica around San Lorenzo Maggiore - and discover more beyond

Oh, and one more thing: stand open-mouthed in front of the Duomo on a sunny day. You don't really need to put this on your list; all streets and trams lead to the Duomo and you’ll inevitably end up there wherever else you go.

Milan travel guide for women - tram in MilanEvery time I rode a tram, I ended up at the Duomo!

I was a solo woman in Milan, free as a bird, so I roamed. Even if you only have 48 hours, you'll see plenty – yes, even in the rain.

Here are some of the things I tried, and a few I didn't - but would if I returned.

  • Riding the trams around town (this I tried). Whenever the rain or the cold got to me, I hopped on a tram for a bit of sightseeing and got off wherever temptation struck.
  • Don’t follow in my footsteps. Take the Duomo rooftop walk.
  • Reserve well ahead of time to see an opera at La Scala. When I looked up the opera, the only available seats were €100 and above. If you can’t have an opera, at least take the La Scala guided tour.
  • Visit the Museo del 900 right next to the Duomo. If you like early modern art, this is your chance to stroll through Italy’s 20th century painting and sculpture, with good explanations (in English) of its various artistic movements and their origins.
  • Go shopping. Window shopping. Leave your credit card at home. The Quadrilatero d’Oro (Metro Montenapoleone) is a squarish area stuffed with designer shops (and the latest fashions – you’ll see them here first). Lining one edge of the ‘quad’ is Montenapoleone street, or Montenapo, world-famous for upscale fashion. Wander around and wave to Armani or Gucci or Dolce & Gabbana as you walk by. Or go in. The Milanese are friendly and courteous and will be delighted to liberate you from your funds.
  • Visit the Sforza Castle. It’s not as spectacular in the rain but it’s not far from the center of town and quite spectacular.
  • Drop by Eataly and have a chestnut cream sundae… and sit back and sigh. You deserve it – Eataly isn’t that well served by public transport so expect to walk a bit.
  • When you’re seeing the Last Supper, go into Santa Maria delle Grazie, the church next door, which has a sober but harmonious interior.
  • Stroll through the campus of the Catholic University (Europe’s largest) and enjoy the student ambience and the glorious cloisters. The list of courses, many in English, are displayed electronically and you might feel a bit nostalgic for your student days.

There’s so much more to do in Milan! You could visit the city’s many museums, go to one of the renowned factory outlet, walk around Sempione Park, or even take a day trip out of the city to the gorgeous Italian lakes region.

But even with a short weekend, you'll already be able to get a strong sense of Milan, Italy's northern capital.

Milan travel guide for women - patioOne of many patios and courtyards in Milan's Quadrilatero d'Oro

Things every Woman on the Road should know about Milan

  • Milan is quite small – at least the center is. I walked about 10km a day (in the rain and fog) but the city is compact enough.
  • I’m not convinced about the Milano Card, which provides discounts and free transport. The public transit authority will sell you a one-day pass for €4.50 and while you can get to and from Linate Airport, it doesn't include the more distant Malpensa airport, which IS included on the Milano card. The card does offer some freebies but it's complicated: you need to download them – and given Milan’s awful Internet you might not be able to. There’s also a museum card which I haven't tried yet.
  • Speaking of the Internet... very bad. Awful. Even the city’s free Internet is impossible to figure out (at least it was for me, and I speak Italian fluently). I kept accepting to sell my soul and receive their newsletters and be on their mailing list for life but nothing helped, I still couldn't connect. My Airbnb had poor Internet too so in the end I paid up and used my 4G network. Next time I’ll bring my beloved mifi and buy a data SIM card.
  • You’ll see the letters ATM everywhere. These are NOT cash machines. The letters stand for Azienda Trasporti Milanesi – Milan’s public transit system. Which, by the way, is quite good, easy to use and gets you everywhere quickly.
  • If you're hooked on street art, consider taking a Milan street art tour if you're short on time.
  • I used Airbnb (if you're not a member yet, join now and get a discount of $35/€33 on your first stay.) If you're rather stay in a hotel, HotelsCombined compares prices and will find you the cheapest price for the room of your choice.
  • For a major city, Milan appears quite safe for a woman on her own. I walked around at night by myself - using caution and common sense, of course - and never felt concerned. There are many homeless people in the city, sleeping in doorways and along the sidewalk, wrapped in blankets against the cold, hugging their dogs. There are pickpockets - not too many on a rainy day but apparently they operate heavily around the Duomo and Sforza Castle, among other places.
  • For a guidebook I used Fodor’s 25 Best, mostly for some quick pre-trip planning. I carried it around (it’s that light) but in the end was waylaid by my own curiosity. The plastified map it comes with was a godsend.
  • Final piece of advice: eat gelato. All the time, everywhere. I had several a day – in the middle of winter. I slurped my cone in the rain and the fog. And I wasn’t the only one.

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