Highlights of Milan, Italy’s Cosmopolitan City

The last time I was in Milan was also my first visit to a police station. Bag snatched after all these years of vigilantly visiting Italy, it undoubtedly yielded the most stressful night I’ve spent in the country. On the plus side, the officer said my Italian was really good.

It’s my belief that we should endeavor always to undo negative memories and refresh them with positive ones, and so I subsequently decided on a return trip to Milan for a month-long stay to better know Italy’s cosmopolitan heart. I wanted to change the narrative of my experience with the city.

Aforementioned trip aside, my last substantial visit to Milan was in 2015 for the World Expo. I had a good time, but I didn’t feel like I really connected with the place. Like many observe, Milan is not as quintessentially “Italian” as cities like Florence, Venice and Rome. Admittedly, this is a stereotype held by foreigners, much like how many come to Oahu, the island on which I grew up, and claim that Honolulu isn’t “real Hawaii.”

Milan is easily the most modern city in Italy. The home of fashion and finance, it exhibits contemporary ideals (like a giant middle finger statue in front of the stock exchange) and embraces technology more than any other in the country (you can pay for the metro with your smartphone and it works a whopping 90% of the time). Milan is an international city, much more so than other Italian cities I’ve visited, and it’s a big relief for this airline miles collector that nearly every place accepts credit.

That said, modern problems pervade, such as air pollution. This was my only complaint. Despite the rumors of snobby Milanesi from my southern Italian friends, I found everyone in Milan extremely friendly and professional. I cannot stress enough how kind everyone was, bag thieves aside.


Getting around Milan is easy. The Metropolitana di Milano connects travelers to any place they should hope to visit within the city. Milano Centrale, the beautiful and historic central station, will likely be your entry station should you arrive from another Italian city. There are also stations at Porta Garibaldi, Lambrate and Cadorna. Some stations service trains that reach locations in Northern Italy that the other stations don’t, so don’t assume all trains leave from the central station.

I recommend downloading the ATM mobile app so you can buy metro tickets on your phone should you run out of cash at night. Generally, it’s best to stick to physical tickets, as I found the QR readers at the turnstiles don’t always work well. Sometimes a daily ticket will be a better value if you plan on riding the metro often in a 24-hour period. There are also weekly and monthly passes. Before using the metro at night, note the closing times so you don’t inadvertently find yourself stranded someplace.

There are, of course, cabs (if you’re calling them, the meter starts running after the request, even if you aren’t yet in the taxi). Uber exists, but it’s expensive as UberX isn’t available in Milan. A friend suggested iTaxi, but I can’t vouch for it completely as I haven’t used it.

Public restrooms may seem lacking in most Italian cities, but one can easily find a toilet in any café (an espresso costs under a euro in most places, so it’s no big deal). Still, there are places where you can relieve yourself for free. Palazzo Reale, right next to the Duomo, has a restroom that was unattended during the month that I visited. Department stores like La Rinascente and Excelsior Milano have restrooms inside. Some churches like the Basilica di Sant’Ambrogio have restroom facilities. But the best restroom stop is inside the Castello Sforzesco, as it’s also a nice area for a break with a water fountain inside the courtyard.


If you’ve only got a short amount of time in Milan, I recommend starting your adventure at the Duomo di Milano (Milan Cathedral). Enjoy a few hours in the bustling Piazza del Duomo, marveling at the golden Galleria Vittorio Emanuele II (the world’s first modern shopping mall, home of luxury brands and the mosaic of a bull whose testicles have been worn down by tourists spinning on them for luck with hopes of returning to Milan), shopping along Corso Vittorio Emanuele, visiting the Museo del Duomo, and, of course, going inside and atop the Duomo itself. If you have a bit more time, you can visit the Museo del Novecento, a modern museum opened in 2010 which houses 20th-century art.

When you’re hungry, grab some panzerotti from the famous Luini Bakery or a pizza fritta from Antica Pizza Fritta da Zia Esterina Sorbillo, a hole-in-the-wall takeaway spot affiliated with the renowned Pizzeria Gino Sorbillo of Naples, of which there is also a restaurant near the Duomo in Milan. For drinks in the Duomo, my go-to has always been Signorvino. Though it could not be in a more touristy area, the prices are reasonable, the staff are friendly and their wines are magnificent. For dessert, Cioccolatitaliani is a unique and decadent stop for grandiose chocolate-covered gelato delights. There’s also the great standby Grom nearby.

After you’re done with the Piazza del Duomo, take a gander at Teatro alla Scala nearby. Opened in 1778, it’s one of the most famous opera houses in the world. Be sure to book tickets before your trip if you hope to see a show inside.

Head down Via dei Mercanti to Via Dante. This pedestrian street offers more shopping and dining. Admire the historic buildings, including the Palazzo dei Giureconsulti with its giant clock looming over Piazza dei Mercanti, the heart of the city during the Middle Ages.

Continue to the Castello Sforzesco (Sforza Castle) where you could easily spend many hours exploring the numerous museums hosted within. The castle has a rich history beginning in the late Middle Ages and has turned hands and functions several times since. Once you’re done with your visit, head through the castle and leave via the opposite gateway to look upon the sprawling Parco Sempione (Sempione Park), Milan’s central park.

Maybe you’ll see an event taking place in the park, or maybe you’ll want to stop at the outdoor café for a drink. Either way, casually continue to the Arco della Pace at the park’s other end. This area is a great place to experience one of Milan’s greatest creations: the aperitivo. It’s essentially food with drinks in the evening, however the Milanesi take it to a grander level. The lounges here serve bountiful items like meats, cheeses, pastas and even, I once saw, carved roast beef. I’ve visited Deseo twice and enjoyed the atmosphere and food.

Head east through Chinatown to see a different side of Milan. Many of the Chinese immigrated here to work in textiles, so you’ll see plenty of clothing shops in Milan’s Chinatown. It’s also one of the cleanest Chinatowns I’ve ever seen. There’s hip stuff to be found, such as artisan street food and bars like La Chiesetta, an old church that’s now a fun locale with a whole menu of crafted shots.

Continue east towards Porta Garibaldi Station. Catch a glimpse of modern Milan at Piazza Gae Aulenti, a glimmering square encircled by towering skyscrapers, including UniCredit Tower. Nearby, the Bosco Verticale, two residential towers opened in 2014, feature lush greenery implemented in its design. Google’s headquarters in Milan is housed right next to it and, to the north, the “up-and-coming” neighborhood of Isola is worth a visit if you have time.

If you’re looking for a quality meal at this point, check out Ratanà, one of the city’s highest rated restaurants for Milanese cuisine.

Put the skyscrapers to your back as you walk down Corso Como. Visit the art gallery-shop-café 10 Corso Como, being sure to head upstairs to the roof for the view. Head towards Porta Garibaldi, the prominent arch. Eataly, the artisan food market, can be found here. There’s also a great pizzeria called Vasinikò which serves authentic pizza napoletana.

Continue south on Corso Garibaldi towards Brera, arguably the city’s most chic neighborhood, where you’ll find the headquarters of Giorgio Armani. If you like art and fashion, you’ll discover it here, especially during Milan’s annual Fashion Week. When you reach Via Pontaccio in Brera, make a left until you see Via Brera and make a right to find the world-famous Pinacoteca di Brera, one of the greatest museums of Italian paintings. The pinacoteca merits at least half a day, as the collection is robust in size.

When you’re done exploring Brera, head south down Via Brera and Via Giuseppe Verdi until you reach the Teatro alla Scala again. Go right along Via Alessandro Manzoni until you see a little square next to Armani. There are some steps here that are great for relaxing. Head down Via Monte Napoleone, the city’s fashion street. This is the heart of the Quadrilatero della Moda (“Fashion Square”). When done (window) shopping, proceed to Piazza San Babila and back towards the Piazza del Duomo.

If you haven’t visited the Terrazza del Duomo (Terrace of the Duomo), near-sunset is the best time to do it (note the closing times). You can also head up to La Terrazza, the rooftop bar of the department store La Rinascente, and enjoy an aperitivo overlooking the piazza.

What I just described is perhaps the simplest path for garnering a sense of what Milan is about, however it’s only a slight scratch upon the surface of what the city has to offer. Tailor the aforementioned suggestions to your length of stay and the timing in which you reach each area (obviously, you can’t have aperitivo or shots for breakfast, you lush). Above all, take the experience slowly, as Italy is meant to be enjoyed.


Milan doesn’t offer as much in terms of typical street food when compared with other Italian cities like Naples. The famous panzerotto seen everywhere actually comes from the south. There’s Spontini, the chain serving thick pizza sliced into cubes, as well as numerous panini options. That said, anything you could want can be found da asporto (“for taking away”) in this international city, whether it be pizza, Sicilian snacks or Chinese bao.

Milanese cuisine consists of dishes such as risotto and cotoletta (breaded veal cutlet). Many restaurants serve Milanese food of varying qualities and costs. I personally liked Il Magentino, a bistro along Corso Magenta, for casual but well-prepared Milanese food.


Open, a bookstore cafe near Porta Romana, is a cozy place for coffee, to work and to find cool gifts. It’s my favorite coffee shop in the city. I would be here every day if I lived nearby. Also great is Colibrì, a bookshop, bistro and live music venue. Located near the Università degli Studi di Milano, it serves the local students well with coffee, cocktails and cuisine.

Across from the Duomo, the Motta Milano 1928 coffeehouse inside the Mercato del Duomo offers great coffee with a view of the cathedral. I met a friend here in the morning and found it surprisingly uncrowded, however I could imagine it could easily become a scene.

There are many Caffé Napoli locations throughout the city. It’s the best quick coffee I’ve found. Each cup comes with a small spoon of their foamy sugar, the cremina napoletana. Normally I don’t take sugar (it must be black like my heart), except when offered their heavenly cremina.

Finally, seek out the independent torrefazioni (coffee roasters) in the city. I visited Torrefazione Hodeidah, a small coffee producer in Milan since 1946, and had a nice chat with the owner about his many coffees and their production.


Mentioned already are the Museo del Duomo and the Museo del Novecento located in the Piazza del Duomo, as well as the exhibits inside the Castello Sforzesco and the wonderful Pinacoteca di Brera. Other notable museums I thoroughly enjoyed include the Pinacoteca Ambrosiana (Renaissance and 17th-century Lombard art) and the Galleria d’Arte Moderna di Milano (GAM, the modern art gallery, located in the historic Villa Belgiojoso Bonaparte).

Many who visit Milan hope to see Leonardo da Vinci’s Cenacolo Vinciano (The Last Supper) at the Chiesa di Santa Maria delle Grazie. If you’re one of these people, book online way in advance. I ended up getting a ticket with an Italian guide at the last minute. Once you’re inside, your group is given a short time to view the fresco, so be sure to take your (non-flash) photos quickly. I was so busy listening to the guide that the only capture I got was this blurry photo taken with my smartphone while I was being rushed out.

As for notable churches, the city is full of them, so I’ll only name my favorites…

The Basilica di Sant’Eustorgio is a grand Romanesque church that is said to contain the tomb of the Three Wise Men (the ones who gave baby Jesus all that stuff). The white marble column outside was allegedly pierced by the Devil’s horns in a fight with Saint Ambrose, thereby earning it the moniker, the Devil’s Column. Supposedly one can smell sulphur and hear the sounds of Hell when near said holes, while others say it’s a doorway to Hell. From personal experience I can say that neither are true, and these unholy holes are wholly ordinary (I hope).

One of the most beautiful churches is the Chiesa di Santa Maria della Passione. The Conservatorio di Milano “Giuseppe Verdi” is located next door, and visitors can catch live musical performances here.

The Chiesa di San Maurizio al Monastero Maggiore features the most impressive and colorful frescoes in the city, painted in the 16th century. In the back is the hall of nuns, where one finds even more artwork. This church is perhaps the most rewarding of quick and free visits.

The grand Basilica di San Lorenze Maggiore sits near Porta Ticinese. it’s a nice place of reflection with plenty to see within. Also big and beautiful is the Basilica di Sant’Ambrogio, which I mentioned earlier because they have a toilet. (It is right to give thanks and praise.)

For something creepier, visit the Chiesa di San Bernardino alle Ossa and its ossuary, a room decorated with human skulls and bones. Cleanse your palate at the Basilica di Sant’Eufemia, a small church with a colorful interior, brilliant blue ceilings, and black and white stripes reminiscent of the Siena Cathedral.

Notable churches near the Piazza del Duomo include the Basilica di San Carlo al Corso along Corso Vittorio Emanuele II, the Chiesa di San Babila, the Tempio Civico di San Sebastiano and the Basilica di Santa Maria presso San Satiro.

(Also worth peeking into: the Chiesa di San Marco, the Basilica e Cripta di San Giovanni in Conca, the Chiesa di San Gottardo in Corte, the Basilica di San Simpliciano, the Chiesa di Santa Maria dei Miracoli presso San Celso, the Chiesa di San Francesco di Paola)


Every so often you need to see something green to undo the urban nature of a big city. Milan is full of lovely parks aside from Parco Sempione. Near Porta Venezia are the large Giardini Indro Montanelli (Indro Montanelli Public Gardens). The Civico Planetario Ulrico Hoepli (planetarium) and the Museo Civico di Storia Naturale di Milano (natural history museum) are both located here. GAM, situated across from the park, also has its own gardens behind it, the Giardini di Villa Reale.

The university is worth visiting for the Ca’ Grande (“the big house”) in which the school resides. The courtyard is a pleasant place to rest if you don’t mind sitting with students. The Giardino della Guastalla, a large park with a lake, is also in this area. The Rotonda della Besana, a green area originally owned by the Ospedale Maggiore, is a six-minute walk away. This peaceful circle of columns also houses the Muba Museo dei Bambini (children’s museum).

If you’re looking for a peaceful retreat from the Piazza del Duomo, head through Palazzo Reale to find a small and romantic park with chairs.

Honorary mention goes to the Giardino di Via Terraggio located in between buildings and accessible by a small door along Via Terraggio off Corso Magenta. It’s the type of nondescript “secret garden” that makes “travel experts” salivate, but it’s really just a small dog park with a playground.


It’s imperative that nightlife lovers visit the Navigli District. On peak nights, the numerous bars along the city’s two canals are crowded as [expletive]. It’s an experience, one that’s entertaining for revelers but also no doubt annoying for those who reside in the area. There are plenty of bars and eateries of all sorts, and many of them get packed, so head there early if you want a seat. One wonders what Leonardo da Vinci, who designed the canals, would think of the scene. I really liked Brass Monkey for affordable cocktails and Al Coccio for craft beer.

The area near Porta Ticinese, right next to the Darsena harbor and the Navigli, is also a prime spot for gathering. Watch as cool young folk gather around the Colonne di San Lorenzo (Columns of San Lorenzo), a row of Ancient Roman columns, as they prepare for an evening at one of many nearby hotspots.

As mentioned earlier, the aperitivo is the classic Milanese tradition when it comes to going out at night. The culinary offerings are so bountiful some even call it apericena (cena, being Italian for “dinner,” because who needs another meal after?). The Arco della Pace area is a straightforward place for the full-blown aperitivo, however many places in the city offer great variations of their own.

As much as I love a good Spritz (with Campari or Cynar instead of Aperol for more flavor and less sweetness), I stuck with the Negroni Sbagliato in Milan. It was invented at the famous Bar Basso here and it’s stronger. Cocktail lovers ought to check out Nottingham Forest, a craft cocktail bar that’s highly ranked among cocktail people in the cocktail magazines they apparently cocktail read. I didn’t visit the latter but I did visit the former; an early afternoon arrival will find you a nice seat in the historic Bar Basso without any wait.

Unlike many Italian cities, Milan offers good options for locally produced craft beer. Most notably, there’s Birrificio Lambrate near Lambrate Station. The original location is what you’d expect from a hip and divey pub with great beer. At night the crowd spills out onto the street, recalling imagery of post-work London. BQ is also a really great brewery with unique offerings, and they have several locations throughout the city.

Perhaps my favorite nightlife find was CerVín, a cozy wine and cocktail lounge with charcuterie plates during aperitivo. Their drinks were the best I’ve had in Milan and it’s romantic enough for a date (which I was on at the time — don’t ask).

For cheap drinks, one must visit Ostello Bello Grande and Ostello Bello, two hostels with lounges inside that are open to the public. These are truly international venues, as many of the clientele are travelers. Ridiculously cheap cocktails in big glasses can be had here.

The eclectic Porta Venezia area features a variety of hip locales for imbibing. The west side of Corso Buenos Aires (a major shopping street) near the gate hosts a number of international eateries as well.

For ultimate luxury, head to the top of the exquisite Excelsior Hotel Gallia near Milano Centrale. This veritable palace features a gorgeous rooftop lounge with delicate bites and well-crafted cocktails. It’s a pricer lounge, but it’s such a stunning place with friendly and unpretentious service that the price is warranted.

As you can gather from this verbose post, there is lots to experience in Milan. Did I have a good time? I most certainly did, and gone are the bad memories of having my stuff stolen. I can now frame that police report as a weird souvenir from a city I thoroughly love.

Finally, photos. Tap and hold (mobile) or hover over (desktop) for descriptions. If you like what you see, please join me on Facebook, Instagram and Twitter

Galleria Vittorio Emanuele II

Piazza del Duomo in Milan

Inside the Milan Duomo

Via Dante in Milan

Teatro Scala

Piccolo Teatro in Milan

Palazzo Reale Milano

L.O.V.E. Statue in Piazza Affari

Milan's Brera District During Fashion Week 2017

Burberry Milan

Steps Outside Armani

Castello Sforzesco

Arco della Pace

Porta Venezia in Milan

Corso Buenos Aires in Milan

UniCredit Tower from 10 Corso Como

Corso Como in Milan

Bosco Verticale

Colonne di San Lorenzo

Basilica di San Lorenzo Maggiore

Porta Ticinese

Navigli District

Street Art in the Navigli District

Chiesa di San Maurizio al Monastero Maggiore

Basilica di Sant'Ambrogio in Milan

Igor Mitoraj Sculpture Outside the Chiesa di Santa Maria del Carmine

San Bernardino alle Ossa

Streetcar in Milan

Rotonda della Besana

Risotto alla Milanese at Magentino

Bar Basso in Milan

Rainy Corso Buenos Aires in Milan

Arco della Pace

Moscova Milan

UniCredit Tower from Piazza Gae Aulenti