In short
Milan is Italy's economic capital and behaves like it: it works, it is less demonstrative than Rome or Florence, and most of what it has to offer requires knowing where to look.
The Duomo and the Galleria Vittorio Emanuele II form the centre. Brera is the district of galleries and lanes. Navigli, around the surviving canals, holds the nightlife. Porta Nuova and CityLife are the contemporary tower districts.
Arriving and getting around
Three airports, and the confusion is expensive. Linate is seven kilometres from the centre, linked by metro. Malpensa is fifty kilometres out, with an express train. Bergamo-Orio al Serio, used by low-cost airlines, is also fifty kilometres away and is not a Milan airport: it is served only by bus.
The metro is efficient and covers the city. The centre is walked.
Milan is the rail hub of the north: Venice, Florence, Turin and Switzerland are within fast-train reach.
What it really costs
Milan is the most expensive city in Italy, housing above all.
The Milanese aperitivo is an economic institution as much as a social one: the price of a drink gives access to a buffet, which often replaces dinner.
When to come
April–June and September–October. Summer is hot, humid and the city empties in August — many businesses close.
Fashion Week and above all the Salone del Mobile, in April, send accommodation prices through the roof and fill the city. Book months ahead or avoid those dates.
Winter is cold and foggy, with regularly high air pollution across the Po plain.
What nobody tells you
Leonardo's Last Supper must be booked weeks in advance. It is in the refectory of Santa Maria delle Grazie, visited in limited-size groups on fifteen-minute slots. There is no last-minute ticket: it is full or it is not.
The Duomo terraces can be visited, on foot or by lift, and you walk among the spires and statues. It is the best thing to do in Milan and a share of visitors does not know it.
The Monumental Cemetery is an open-air sculpture museum, free, and almost empty.