Milan

Why go

The fashion system, not just the shops — showrooms, ateliers, printers and press offices in the same square kilometre. Design as an industry — the Salone del Mobile fills the city each April with the world's furniture trade. Northern Italian wealth on display — a stock exchange, a cathedral of a hundred and thirty-five spires, and La Scala. The Last Supper — fifteen visitors at a time, twenty minutes, booked months out.

The character

Milan is the least Italian-looking Italian city and the most productive one, and both facts come from the same history: bombed heavily in 1943, rebuilt in a hurry, and then made rich by manufacturing. Fashion did not arrive as glamour but as supply chain — the silk of Como, the wool of Biella, the shoe factories of the Marche and the Veneto — and Milan supplied the offices, the buyers, the photographers and the press that turned all that production into an industry with a calendar.

That calendar is the city's clock. Fashion weeks in February and September, the Salone del Mobile in April, and in between a working town that starts early and takes aperitivo seriously. Milan hides its pleasures behind façades: the courtyard is the fundamental Milanese unit, and the difference between the street and what lies inside a gate on Via Montenapoleone or Corso Magenta is the whole lesson. Visitors who judge the city from its ring roads leave disappointed; those who get through a few doors understand why Italians who want to work move here.

Places of character

The Duomo roof — walk among the spires and statues; the interior is dark but the terraces are the point. Pinacoteca di Brera — Mantegna's foreshortened Dead Christ and Piero's Montefeltro altarpiece, in an academy still teaching. Fondazione Prada — Rem Koolhaas's converted distillery with a gold-leafed tower and Wes Anderson's bar. Navigli at dusk — the surviving canals Leonardo worked on, now the evening drinking quarter. A courtyard on Corso Magenta or Via Bagutta — push a gate and find a garden the street gives no hint of. Cimitero Monumentale — the industrial families' mausoleums, an open-air museum of a century of Milanese ambition.

The way to do it

Book Santa Maria delle Grazie months ahead for the Last Supper; there is no other way in. Treat aperitivo between six and eight as the social institution it is. Shop the Quadrilatero for the windows and the outlet towns for the prices. And look through gates: the city's architecture is inward and will not come to you.

One perfect day

Espresso standing at a bar, then the Duomo roof at opening with the Alps sometimes visible to the north. Walk to Brera for the gallery and the streets of the academy quarter. Lunch of risotto alla milanese and a glass of Franciacorta. Afternoon at Fondazione Prada in the old distillery, then back for the Last Supper slot at four — twenty minutes, and the wall is far stranger than reproductions suggest. Aperitivo on the Navigli or in Brera, where the negroni comes with enough food to skip dinner. Then dinner anyway, late, in a trattoria that has been serving cotoletta since before the war.

Grand hotels

Bulgari Hotel — a converted eighteenth-century palazzo with a four-thousand-square-metre private garden behind Montenapoleone. Grand Hotet et de Milan — 1863, where Verdi lived for twenty years and died; the rooms are kept as they were.

When to go

Best expression: April during the Salone del Mobile, when the whole city becomes an exhibition and every courtyard opens. Consider: October, mild and working, with the opera season opening and no trade fair crowds. Avoid if possible: August, when Milanese leave en masse and half the restaurants close, and fashion weeks if you need a hotel room.

The frame

Ideal stay 2 nights · Minimum 1 night · Best arrival high-speed rail; milano Centrale is a monument in itself · Airport MXP 50 km, LIN 8 km · Walkability good in the centre, with a dense metro beyond · Best without a car yes