What should I avoid in Milan?

Piazza del Duomo is where most first-timers lose money in their first hour, and it rarely involves a pickpocket. Men near the cathedral steps tie a woven string bracelet onto your wrist, call it a gift, then block your path asking for €5 or €10; keep your hands in your pockets and keep walking toward Via Mercanti, because a firm 'no, grazie' ends it. The pigeon trick works the same way, with a fistful of corn pressed into your palm and a bill to follow. Inside Galleria Vittorio Emanuele II, the cafe tables under the glass dome charge €15 or more for an Aperol spritz that costs about €7 in Brera, so stand at the marble counter of Camparino in Galleria instead: a Campari soda at the bar costs a fraction of the table price, and you still hear glasses clinking off the mosaic floor. For a cheap lunch near the cathedral, Luini on Via Santa Radegonda sells hot, oily panzerotti stuffed with mozzarella and tomato for around €3.50, and its queue moves fast.

The most expensive mistake in Milan is assuming you can see Leonardo's Last Supper on the day. The refectory at Santa Maria delle Grazie, a UNESCO World Heritage Site, lets in small groups for 15 minutes at a time, and the official cenacolovinciano.org site releases tickets in quarterly blocks that tend to sell out within days. Base entry currently runs around €15 plus a small booking fee. Resellers on Corso Magenta and on third-party sites bundle the same slot into 'tours' priced at €50 to €70, and if the official calendar is gone, a guided Viator or GetYourGuide slot is the honest fallback. Check that the listing names refectory entry, because some Corso Magenta 'tours' walk past the church facade and no further. The room is cool, dim and climate-controlled, and the timer feels short, so get to the Piazza Santa Maria delle Grazie entrance 20 minutes early.

Arrival day in Milan has its own traps. In the Malpensa Terminal 1 arrivals hall, unlicensed drivers offer rides, but licensed white taxis wait at the outside rank and charge a fixed fare of about €110 (roughly $123) to central Milan. The Malpensa Express costs €13 and reaches Cadorna in about 37 minutes or Milano Centrale in about 50, which beats a cab stuck in Friday traffic on the A8. Coming in from Linate, the M4 metro gets you to San Babila in about 12 minutes on a standard €2.20 ATM ticket. On ATM trams, validate a paper ticket in the yellow machine on board or tap a contactless card. Inspectors on tram 1 and the M1 hand out fines on the spot. The crowded escalators at Duomo and Centrale stations are where pickpockets work, so keep your phone in a front pocket. Piazza Duca d'Aosta outside Centrale gets edgy after 11pm. Milan scores 7.2/10 for solo-traveler safety (see the TTDI Solo-Safety Index), and the realistic risk here is petty theft, not violence.

Skip the all-you-can-eat apericena buffets along Alzaia Naviglio Grande, where €12 buys you a sugary spritz and trays of lukewarm pasta salad under heat lamps. The Naviglio Grande is lovely at dusk, so walk it, then go for a drink at Bar Basso on Via Plinio, where the Negroni Sbagliato was invented in the early 1970s and still comes in an oversized, ice-cold goblet. Milan's calendar matters too: the Pinacoteca di Brera and the museums inside Sforza Castle close on Mondays, which wrecks a lot of first-day plans, and hotel prices can triple during Salone del Mobile in April and during Fashion Week in February and September. Book months ahead or pick other dates. Around Ferragosto in mid-August, many family trattorias in Porta Romana and Isola close for two or three weeks. November brings damp fog in from the Po Valley, and July afternoons often go past 32°C, with mosquitoes along the canals.