Famed for fashion, opera, and the many-spired Duomo, Milan is the powerhouse of international business in Italy. It gets a bad rap as being boring, unattractive, or excessively modern, but that’s often from people who haven’t spent much time there.

No, it’s not Rome, Venice, or Florence. Yes, it’s a big bustling city with a business focus, and it has many new buildings due to being bombed heavily in the Second World War, but it was at one time the capital of the Roman Empire, the seat of the Visconti and Sforza Dukes of Milan during the Renaissance, and subsequently influenced by the Spanish, French, and Austrians.

It is full of history and culture, with discoveries big and small around every corner. It is also much less touristy than the other famous cities. While it sits on a perfectly flat plain, Lake Como is nearby and the Alps are visible on a clear day – a bit rare in spring and fall due to the fog (and smog) that often hang over the city.

CONTENTS

1. Top Sights
2. Less Busy Sights
3. Slightly Offbeat Sights
4. Best Piazzas
5. Best Views
6. Best Day Trips
7. Best Walks
8. Local Cuisine
9. Transportation
10. Where to Stay

Top Sights

THE DUOMO

The work of six centuries, this was only completed in 1965, and there is a joke that something that takes forever will be done when the Duomo di Milano is complete. Essentially Gothic in style, and supremely impressive with its ascending spires, the cathedral is the third-largest in the world by area, surpassed in Europe only by St. Peter’s in Rome.

LA GALLERIA VITTORIO EMMANUELE II

The world’s first shopping mall, and still the most beautiful, this is a massive glass-covered indoor/outdoor arcade connecting the Duomo and La Scala, with mosaic floors and many of Italy’s most revered brands, plus Pasticceria Marchesi. 

TEATRO ALLA SCALA

The world’s most famous opera house. It’s beautiful but relatively unassuming from the outside, though it has gilt and red velvet Baroque interior and every bold-faced name in opera has graced its stage since the 1700s. If you visit outside of the summer, try to catch a performance.

THE LAST SUPPER (IL CENACOLO VINCIANO) AND SANTA MARIA DELLA GRAZIE

Leonardo da Vinci decorated the refectory of Santa Maria della Grazie using an experimental technique that started peeling immediately. Today, the work is largely reconstructed, but it it’s still the hardest ticket to get in Milan. Book months in advance. Note: don’t miss the church itself (above). For many people it’s an afterthought but it is a masterpiece of Renaissance architecture by Bramante (in part) and has the most beautiful painted ceiling in the city.

PINACOTECA DI BRERA.

Milan’s main museum, in its most beautiful neighborhood. It’s not the same caliber as the Uffizi or the Vatican, but it features a nice Caravaggio, and works by Raphael and Piero della Francesca (above right), among many lesser known masters (check out the odd but beautiful gilt late Gothic works of Carlo Crivelli).

QUARTIERE DELLA MODA (MONTENAPOLEONE)

The most famous shopping area of the city and all of Europe. All the top brands are here. Via della Spiga in Montenapoleone is a pedestrian street and a popular place for a passegiata as window shopping is free.  

CASTELLO SFORZESCO AND PARCO SEMPIONE

One of the largest castles in Europe, built by the Visconti and Sforza lords of Milan during the Renaissance. It’s beautiful and features several museums and an unfinished Michelangelo sculpture. It’s free to enter the court. The castle is set in the gorgeous Parco Sempione with beautiful vistas to the Arco della Pace, and the Palazzina Appiana, an arena/palace built by Napoleon.

Note: all over the castle (and elsewhere) you will see a seal of a snake devouring a man up to his torso. This is the biscione, the heraldic emblem of the Visconti, the first great lords of Milan, and the snake is actually giving birth to a child, symbolizing the origin of the family. The Sforza later adopted it, and it has become a sort of unofficial seal for the city.

NAVIGLI.

The canals of Milan. It’s not Venice, by a long shot, but there are fairs here and countless restaurants and bars (generally very crowded with a young clientele).

Less Busy Sights

BASILICA DI SANT’AMBROGIO

This is among the oldest churches in the city, founded by St. Ambrose, who is Milan’s patron saint. It dates back over 1600 years and you can feel the continuity in the cool dark interior when the incense burns. Not to be missed.

FONDAZIONE PRADA

Designed by Rem Koolhaas’s OMA, this is a massive contemporary art complex in a converted distillery, with some ground-up construction including a tower covered in 24-carat gold. There is also a café designed by Wes Anderson and the outstanding Ristorante Torre at the top, with some of the best views of Milan. (image courtesy Bas Princen and Fondazione Prada).

VILLA NECCHI

Built in the 1930s, this is the ultimate Art Deco townhouse set in lush grounds hidden behind a high wall. For some reason, the original owners furnished it with Louis XIV-style furniture which clashes with the clean lines of the beautiful building, but they got everything else right.

PIRELLI HANGAR BICOCCA

This former tire factory was converted into a contemporary art space featuring rotating art shows and an Anselm Kiefer permanent exhibition. The space is one of the largest you will ever stand inside.

MUSEO BAGATTI-VALSECCHI

An eclectic collection of medieval and Renaissance furniture and arms and armor inside a magnificent Milanese townhouse.

TRIENNALE DI MILANO.

Milan is famed for design with the annual Salone del Mobili fair. This is its design museum, set on the side of Parco Sempione. It features the best of Italian design including the 1980s Memphis Style pioneered by Ettore Sotsass. It also has a large grounds with sculptures, a bar, and occasional concerts.

Biblioteca Ambrosiana, a library containing important medieval manuscripts and also illustrations by Da Vinci and Rapahel, with a full-size cartoon of his School of Athens.

Massimo di Carlo Gallery, Italy’s top contemporary art gallery in a magnificent art deco apartment converted into exhibition space.

Nilufar Depot, an internationally renowned design gallery.  

San Maurizio, which is almost completely covered in 16^th Century frescoes. One of the hidden gems of the town.

Slightly Offbeat Sights

SANTUARIO BERNARDINO ALLE OSSA

If you want to see a chapel decorated with hundreds of human skulls – and I wouldn’t fault you if you do – this memento mori is for you. The bones probably come from an ossuary belonging to the nearby Brolo hospital, in existence since the 12th Century, and possibly the friars who worked there, and convicted criminals. Whosever they are, it’s quite the design scheme.

IL DITO (THE FINGER)

The piazza outside of Borsa Italiana has a Maurizio Cattelan sculpture that is a hand giving a gigantic middle finger entitled L.O.V.E. (Libertà, Odio, Vendetta, Eternità) – or Liberty, Hate, Revenge, Eternity – but usually just called “the Finger.”

LEONARDO’S HORSE

In the 15th Century, Leonardo (da Vinci, of course) was commissioned by Duke Ludovico Sforza to make a massive bronze equestrian statue. Like so many of his projects, it was never completed. The closest he got was a clay model. But, he left many drawings and in 1999, after decades of research and experimentation, a 24 ft tall horse was cast in bronze and placed at the Hippodrome (racetrack) in Milan. You can see it there today. Probably worth it only if you are in the neighborhood of San Siro.

Best Piazzas

Piazza Duomo, outside of the Duomo, with the entrance to the Galleria. It can be insanely crowded, but is a magnificent public space.

Piazza Castello, the vista of the castle, the fountains, and back down Via Dante toward the Duomo is gorgeous. On the opposite side of Parco Sempione is Piazza Sempione with the Arco della Pace, also built by Napoleon, and vistas all the way to the Castello.

Piazza Sant’Ambrogio, with the city’s most important basilica.

Piazza Tomasi di Lampedusa, a hidden piazza with Roman ruins.

Best Views

The Duomo, the top of the cathedral has a famous viewpoint.

Fondazione Prada, from the top of the galleries you can see the Duomo itself and all the way to the Alps.

Monte Stella, this is a park with a hill built from debris of the bombing in the Second World War. It’s far afield for most tourists, but features amazing views of the city and the Alps.

The restaurant on the terrace at Museo del Novecento.

Best Day Trips

Lake Como is the obvious choice. The lake is shaped like a wishbone, or an upside down Y. Either arm is nice, including the more famous Como (west), and Lecco on the other (east) side. Bellagio (in the middle where the arms meet) is perhaps the top spot but requires a car, bus, or ferry from one of the towns.

Best Walks

1) Visit the ancient Romanesque Basilica di Sant’Eustorgio and walk north along Corso di Porta Ticinese, passing the Colonne di San Lorenzo, arguably the most impressive Roman ruins in Milan. Left on Via Lanzone until you reach Basilica Sant’Ambrogio. Pass the Templo della Vittoria monument and continue to San Maurizio, which has exceptional frescoes. Continue toward Piazza Tomasi di Lampedusa, where you will see the remains of the Imperial palace and bath complex during the 3^rd-4^th Century AD, and the medieval tower, Torre dei Gorani. Continue to Borsa Italiana to see the Maurizio’s Cattelan middle finger.

2) From La Scala, pass through the Galleria Vittorio Emmanuele, into Piazza Duomo. Turn into Piazza dei Mercanti with its medieval ruins, and then into Piazza Cordusio. Follow Via Dante toward the Castello, this is one of the great passegiatas in Milan (and will be busy). Walk through the Castello, which has a nice café, and into Parco Sempione with exceptional vistas of L’Arco della Pace; wander the park either right (to see the Palazzina Appiana, built by Napoleon) or left (to see the Triennale). End at L’Arco della Pace for aperitivo at one of the many cafes.

3) From the San Babila stop, walk up Via Monte Napoleone, the most famous shopping street in Milan. You can make a quick detour to Museo Bagatti Valsecchi. When the pedestrian street ends, turn left at Via Monte di Pieta, and a quick right on Via Brera. Follow this (also pedestrian) past the Pinacoteca and Botanical Garden. Possible quick detour to Piazza San Marco on your right. Follow Via Solferino to Moscova stop. Link it with the below walk.

4) From Moscova, turn slight right on Corso Garibaldi and continue north. Pass the beautiful Chiesa Santa Maria Incoronata, and proceed through the Arch of Porta Garibaldi. You should have a view of the Bosco Verticale, the Vertical Forest which is an apartment complex covered in trees. Make a detour up Corso Como, one of the most famous streets in the city, then come back toward the gate. Turn toward right before the Gate itself, passing the Microsoft building. When you reach the intersection, note the monumental entrance of the Cemetery to the right. Eventually the street becomes Via Paolo Sarpi, the main thoroughfare of Chinatown. It’s not NYC Chinatown, but there is amazing street food and a good vibe.

In my opinion, the best town that you can visit by train is Varenna on the east side of the lake, just over an hour from Milan. It has both exceptional views and a beautiful town center; it is very small and most of it – unlike Como – is situated right on the lake. There is ferry access from many other points.

Monza, 10 minutes away, a separate city that has become almost a suburb of Milan (don’t say that in Monza). It has a magnificent cathedral (a UNESCO site in its own right) with a dramatic striped facade that holds The Iron Crown of Lombardy, a ~1500 year old crown made mostly of gold but with a band of iron said to be from one of the nails on the True Cross, and used in the coronation of kings in Italy for centuries. The other attraction is, and massive park with the impressive Palazzo Reale. They hold the F1 races here annually. Worth a visit given its proximity.

Bergamo, with its “Alta Citta” (high city) on hilltop at the foot of the Alps. It includes the Basilica di Santa Maria and the attached Colleoni Chapel, with the tomb of the famed Renaissance condottiero (military commander) Bartolomeo Colleoni.

Local Cuisine

Lombardian cuisine has strong influences from the north. It won’t look “Italian” since it has no red sauces and pasta is replaced by polenta and risotto. But it’s excellent. Some of the key dishes are:

• Osso buco and risotto milanese, this is the must-try classic dish
• Cassouela, similar to cassoulet
• Polenta, cornmeal like grits only better, and the staple of Lombardian cuisine
• Mondeghili, less-seen but excellent fried meatballs
• Pizzocheri, a traditional pasta from Valtellina made with grano saraceno and cheese
• Casoncelli, a stuffed pasta originating in nearby Bergamo
• Taleggio and gorgonzola cheese
• Panettone, the classic Christmas dessert, it’s a type of fruitcake, but light and fluffy and nothing like the bricks we sometimes see in the U.S.  
• Franciacorta wine 

RESTAURANTS

Classic Milanese cuisine:

• La Libera, a classic in a classic space with a sartorial owner.
• Stendahl, with a stylish interior but excellent traditional recipes.
• Trattoria Milanese dal 1933, where the decor matches the name, serving the most typical Milanese recipes.
• La Bettola di Piero, a no-frills trattoria with fantastic food and friendly staff.
• Bar Basso, not much food here besides the chips for aperitivo, but it’s the most famous bar in Milan and home to the Negroni Sbagliato in a big glass.

Other:

• Cirispaccio, if you want that red sauce lacking in Milanese cuisine, this Napoletana spot is as good as Naples.
• Horto Milano, if you are looking for Michelin stars.
• Marchesi 1824, a pasticceria with multiple locations including the Galleria.
• Sapori di Shanghai, for dim sum, and all the street food stands on Via Sarpi.

Favorite Gelato:

• Gelato e Champage – Cerdini & Quenardel dal 1906. I like this place with a great combination of creamy and fruity flavors, and yes, champagne. It’s less touristy than the stuff in the center (i.e. Venchi).
• Crema Alta Gelateria, a good option in Brera.
• Gusto 17, just off Piazza Sempione near L’Arco della Pace. It’s a tiny little window, but it’s exceptional. If you are in the neighborhood don’t miss it.

Transportation

It’s easy to get in and out. Milan has 3 airports (Malpensa, Bergamo, and Linate, connected to the center by train, bus, and subway, respectively). Along with the massive train hub at Milano Centrale they make it the best-connected city in Italy.

It also has one of the best local transport systems of any city in the country, with 5 metro lines, regional trains, and the famous classic trams. It also has a bike share system that is so cheap it’s almost free (BikeMi); and you can find Lime and Bird bikes and scooters but beware the paving stones. That said, much of the historic center is walkable.

Cabs are expensive and can only be hailed at taxi stands, and with apps like FreeNow.

Where to Stay

Since I had an apartment here, I have little experience with this, but I suggest:

Brera, Porta Nuova and Porta Venezia, but anywhere inside Zone A (the center with restricted traffic zone) is easy.  

Isola, a little out of the way but hip.

I would avoid staying right near Milano Centrale, though there are many hotels.