Four days in Milan: not pretty, and the best evening in Italy

Three nights in the centre, one Leonardo booked months ahead, and enough time to work out why people who live in Italy would rather live here.

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Length
4 days, 3 nights
Where you stay
Milan
Places
10 across 4 days
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Milan gets written off in a sentence: not beautiful, bombed flat, all offices and money, do it in a day on the way to Venice. Every part of that is a little bit true and the conclusion is still wrong.

What Milan has instead of prettiness is depth. A late Gothic cathedral that took nearly six hundred years to finish, a fourth century basilica standing behind a row of Roman columns, a Leonardo wall painting that has been slowly dying since the day it was made, and the best collection of Italian painting outside Florence and Rome. It also has money, which in Italy means the shops, the restaurants and the concert halls are the best in the country.

The other difference is the evening. Northern working cities eat late, drink first, and treat six to eight in the evening as a social institution rather than a gap. Four days here should be planned around that rather than against it.

Highlights

  • The cathedral roof, walking among the spires rather than looking up at them
  • The Last Supper, fifteen minutes in a group of thirty, booked months in advance
  • A church frescoed wall to wall by a painter almost nobody outside Lombardy has heard of
  • Michelangelo's last sculpture, unfinished, in a castle courtyard museum

Where to stay

Milan, three nights

The capital of the Roman Empire's western half for a hundred years, an independent duchy, an Austrian possession, and the city where Italian industry was invented. It has been knocked down and rebuilt more often than anywhere else in the country, most recently by allied bombing in 1943, which is why the streets are broad, the architecture jumps centuries between one building and the next, and the medieval survivals feel like accidents.

It is also a city that does not perform for visitors. Nothing here has been prettified, the good things are behind ordinary doors, and the pleasure of three nights is discovering how much is going on once you stop expecting a picture postcard.

Day by day

Day 1 in Milan

The cathedral, the roof and the opera house

Start at the top. The cathedral is worth twenty minutes inside and an hour on the roof, and the roof is the thing: you walk on the actual stonework between the flying buttresses, at eye level with a forest of carved spires and about three thousand statues, with the Alps visible on a clear winter day.

It took from 1386 until well into the twentieth century to finish, in pink-white marble brought down a canal built specially to carry it, and the result is a cathedral in a style nowhere else in Italy took seriously.

The glass-roofed arcade off the north side of the square leads to the opera house, which from outside looks like a bank. That is deliberate: the plain front was meant to keep the attention on what happened inside.

  1. 14:00

    Duomo

    Religious

    Take the lift up and the stairs down, or the stairs both ways if your knees allow. Inside, look for the sixteenth century statue of a flayed Saint Bartholomew carrying his own skin, which is either the best or the worst thing in the building.

  2. 16:30

    Teatro alla Scala

    Culture

    Opened in 1778 on the site of a demolished church, rebuilt after the bombing, and restored again in the early 2000s. The museum tour gets you into a box looking down at the stage, which is the only way to see the auditorium without a ticket for the night.

  3. 18:30

    Aperitivo, at six

    Eat

    One negroni or one Campari with soda buys a plate of food in most bars in this city, and two of them replace dinner. Sit outside if the weather allows and watch the evening passeggiata.

With more time: The modern art museum on the south side of the square, in the heavy fascist-era palazzo with the spiral ramp inside, has Futurism, Modigliani and Picasso, and a top-floor window looking straight at the cathedral. It opens late several evenings a week.

Day 2 in Milan

The Last Supper, and two very old churches

Your slot is your slot: turn up twenty minutes early and be at the door, because they will not hold it. You are dehumidified in an airlock, let into the old monastery refectory in a group, and given fifteen minutes.

It is a ruin and it is still overwhelming. Leonardo painted it on dry plaster instead of wet so he could keep revising, which meant it started flaking within his lifetime, and what survives is a fraction of the paint on a wall that has since been bombed, whitewashed and restored for twenty-one years. What survives is the composition, and the composition changed European painting.

The rest of the day is within a fifteen minute walk and gets nothing like the same attention. One church has been standing here since Roman Milan, the other is covered in frescoes from wall to ceiling and is usually empty.

  1. 09:30

    Saint Mary of the Graces

    Religious

    The refectory of a Dominican convent, with Leonardo at one end and a Crucifixion by a lesser painter at the other that nobody ever turns round to look at. The church next door is free and worth ten minutes for the domed east end.

  2. 11:30

    Basilica di Sant'Ambrogio

    Religious

    Founded by the bishop who baptised Saint Augustine and still holding his bones in a glass case in the crypt, alongside two martyrs. The brick Romanesque church around them went up in the eleventh century and is the model half of Lombardy copied.

  3. 13:00

    Lunch near Sant'Ambrogio

    Eat

    The university district behind the basilica has cheap places aimed at students rather than at visitors, which in this expensive city is worth knowing.

  4. 15:00

    San Maurizio al Monastero Maggiore

    Religious

    A plain grey box from the street and, inside, every surface painted by Bernardino Luini and his workshop. It was the church of a closed convent, so a wall divides the public half from the nuns' half, and both are frescoed. Free, and often you will be alone in it.

With more time: The science museum a few streets further west has the largest collection of models built from Leonardo's drawings anywhere, plus a submarine you can walk through. It is the obvious afternoon if you are travelling with children.

Day 3 in Milan

The castle, the park and the Brera

The Sforza castle is a fortress rather than a palace, and a set of small museums rather than one big one. Go for two things: the room Leonardo painted as a canopy of interlaced trees, and Michelangelo's last sculpture, which he was still cutting six days before he died at eighty-eight and which looks like nothing else he made.

Behind the castle is the city's big park, and beyond it a triumphal arch Napoleon commissioned and never got to ride through. It is the right place to sit for an hour in the middle of the day.

Then Brera, which is both a neighbourhood and a picture gallery. The neighbourhood is what the centre looked like before the war: narrow streets, ivy, art students. The gallery is one of the great collections in Italy and gets a fraction of the visitors of the equivalent in Florence.

  1. 09:30

    Castello Sforzesco

    Historic

    Red brick, enormous, with a ditch and drawbridge still in place. The Rondanini Pietà sits alone in a bare room in the hospital wing: two figures barely emerging from the block, abandoned unfinished, and more moving for it.

  2. 12:30

    Sempione Park

    Leisure

    The park laid out behind the castle on the old parade ground, with a steel tower from 1933 at one end that you can ride to the top of for the best view of the Alps on a clear day.

  3. 13:30

    Lunch in Brera

    Eat

    Touristy at the edges and genuinely good two streets in. Look for the places with a written-up lunch menu and no photographs.

  4. 15:00

    Brera Art Gallery

    Culture

    Mantegna's dead Christ seen from the soles of his feet, Piero della Francesca's altarpiece with an egg hanging over it, and Raphael's Marriage of the Virgin. Two hours, and never crowded.

With more time: Two streets from the gallery is a house museum kept exactly as two nineteenth century brothers furnished it, in a deliberate imitation of a Renaissance interior, down to the plumbing hidden inside carved cupboards. It is the strangest hour in Milan.

Day 4 in Milan

Roman Milan, and the canals

The last morning goes south, into the part of the city that predates everything else. Sixteen Roman columns stand in a row in front of a basilica founded in the fourth century, when this was an imperial capital and Rome was not.

From there a green strip runs south towards the canals. Milan had a whole network of them once, built to bring the marble in and the goods out, with locks that Leonardo worked on; most were paved over in the 1930s and two survive.

Centrale is twenty minutes away on the metro, so this is a comfortable morning before an afternoon train.

  1. 09:45

    Basilica di San Lorenzo Maggiore

    Religious

    Fourth century in origin and rebuilt several times since, with an octagonal chapel off the side holding a mosaic older than almost anything above ground in Italy. The columns outside were pulled from a Roman building and re-erected here.

  2. 11:15

    Basilicas Park

    Leisure

    The lawn that connects that basilica to another one further south, past the old city gate. Ten minutes of walking, and on a Saturday the flea market at the far end is worth the detour.

  3. 12:30

    Lunch on the canal, then the metro

    Eat

    The Navigli towpaths are ten minutes further and full of places with tables on the water. Touristy at night, ordinary and pleasant at lunchtime.

With more time: The monumental cemetery, north of the centre, is the other thing worth a morning: a hillside of nineteenth and twentieth century tombs commissioned from serious sculptors, which is a stranger and better museum than most museums.

Before you go

Where to stay

Inside the inner ring is small, walkable and expensive on weekdays, because the whole city runs on business travel: hotel prices here fall at weekends and in August, which is the reverse of everywhere else in Italy. Brera and the streets around Sant'Ambrogio are the pleasant end of central.

Navigli, along the two surviving canals in the south, and Isola, north past the new towers, are both cheaper, both connected by metro, and both far better for eating and drinking than the blocks around the cathedral. Around Centrale station is convenient and grim.

Getting around

The metro is fast, clean and actually goes where you want, which after Rome comes as a surprise. Four lines cover everything below, a day ticket costs less than two single fares, and the same ticket works on the trams.

The old orange trams are worth using for their own sake. Some of the cars date from the 1920s, they still rattle around the ring, and one of them has been converted into a restaurant that circles the city while you eat.

Booking the Last Supper

Do this before you book anything else. Tickets are released in blocks a few months ahead and sell out within hours, entry is in groups of about thirty for exactly fifteen minutes, and there is no queue to join on the day. If you miss the release, the official guided tours hold a separate allocation at a higher price and often still have space.

Everything else in the city can be arranged the night before. The cathedral roof is worth prebooking a lift ticket for in summer, and the Brera gallery runs timed entry that rarely sells out.

Aperitivo, and eating

Aperitivo here is not a drink, it is a time of day. From roughly six, bars put out food with the drinks: at the cheap end a bowl of crisps and some focaccia, at the proper end a full buffet that will replace dinner for the price of a cocktail. Campari and its cousins were invented in this city and the bitter red drinks are what to order.

Milanese cooking is butter and rice rather than oil and tomato, which surprises people expecting the south. The three dishes worth seeking out are saffron risotto, a veal cutlet fried in breadcrumbs, and slow-braised shin of veal, and none of them is light. Restaurants here take bookings and expect you to use them.

The people who like Milan are usually the ones who stopped trying to compare it with Florence. It is a working northern city that happens to keep a Leonardo in a monastery and a Michelangelo in a castle, and it does not much mind whether you came.

Give it the evenings and it opens up. That is when the city belongs to the people who live in it, and they are the reason to be here.

Or make it a longer trip

These trips pass through here on the way somewhere else.

Make it your trip

Every stop, day and place here lands in your account as an editable trip. Move the days around, swap a city, add your own bookings and costs, and share it with whoever is coming.

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Common questions

Is Milan worth four days?
If your idea of a city break is walking around looking at a beautiful old centre, no, and Verona or Bologna is a better use of the time. If you want serious art, serious food and a city that is alive on a Tuesday night rather than staged for visitors, four days is comfortable and you will not run out.
How far ahead do I have to book the Last Supper?
Months. Tickets go on sale in blocks a few times a year and the good slots are gone the same day. The official guided tour costs more and holds back places, so check that before giving up. There is no standby queue.
Is Milan expensive?
By Italian standards, yes, and hotels are the worst of it because business travel sets the price. The exception is the calendar: weekends and August are much cheaper here, exactly when the rest of Italy is dearest. Aperitivo is the great value meal in the city.
What about the lakes?
Como is about forty minutes by train from Centrale, or an hour on the slower lakeside line out of Cadorna, which makes it an easy day out and a common fifth day. It is a different sort of trip though, and a night or two on the lake beats a rushed return in the dark.
When should I come?
April to June and September to October. Milan sits in the Po valley, so summer is humid and heavy and winter is grey and foggy, though the fog suits the place. Avoid the big fashion and furniture weeks unless you are attending, because every hotel in the city triples its price.