Milan is widely accepted as a high-end shopping destination but rarely comes up as a sightseeing one. Even the proud locals would agree that Milan is not especially beautiful as there is too much haphazardness to its architecture, with too many sore spots. It is a modern metropolis, but lovely pockets are found here or there, monumental buildings pop up at intervals, attractive lines of residential buildings appear on many streets, and more than one church offers a highlight. High-end shopping may act as a welcome supplement for some.
One sight that should be on everyone’s must-see list is the Duomo ♥♥♥, one of the main claimants to the title of the grandest Gothic churches in the world. The interior is both majestic and a bit glum, with wonderful stained-glass windows offering vivid contrast to the otherwise sparsely decorated space, but the highlight of the cathedral is undeniably its extraordinary roof, with 135 spires and uncounted statues and gargoyles. Being able to walk on the roof is a fairly unique experience in itself, and the views over the city are not half-bad either.
Galleria Vittorio Emmanuele II ♥ is an attractive shops-and-restaurants arcade, with a certain impressive quality of design, especially when it comes to its glass ceiling and dome.
Teatro alla Scala ♥♥ is not too eye-catching from the outside, but a visit to its museum (which allows viewing the famous opera hall from a section of boxes) is worthwhile. The museum displays are centered on famous people associated with the opera, with a few fun musical instruments thrown in.
Castello Sforzesco is as eye-catching as anything in town. It houses a set of history and military museums that may be of interest to some. You can freely walk through the grounds even if you do not go to any of the museums.
A fine art collection at Pinacoteca di Brera ♥♥ is further enhanced by the gallery’s layout and item labeling. Pinacoteca Ambrosiana is, conversely, underwhelming and rather overpriced for what it has to offer. Its main claim to fame is the library with Leonardo’s Codex, which does not compensate for the rest of the collection.
Museo Bagatti-Valsecchi ♥♥ is a very interesting 19th-century mansion designed to evoke 16th-century castles. One other museum that will feature on the itinerary next time is Museo Poldi-Pezzoli.
Leonardo’s Last Supper ♥ requires advance reservation efforts to be visited. If you do go, you may be slightly disappointed by the brevity of the time allocated to you. The church itself, Santa Maria delle Grazie ♥ is rather interesting too.
The church of San Maurizio al Monastero Maggiore ♥♥♥ is among the most incredibly painted churches anywhere. Other churches worth attention are Basilica di Sant’Ambrogio ♥, San Lorenzo Maggiore ♥, and quite a few others.
Of the various neighborhoods at the edges of the city center, Navigli ♥ is the most bouncing at night.
Accommodation-wise, any location in Zone 1 (Centro Storico) will put you within walking distance of most of the points of interest. The extensive transport options make staying somewhere outside of the city center workable as well.
As far as eating out is concerned, whether you reserve a table in advance based on online ratings or just pick a restaurant at random, it is hard to have a truly disappointing meal in Milan. I personally prefer local vibes in less touristy areas, but sometimes sitting down in an eatery on a crowded square can have its rewards.
Worthy of specific recommendations are: Salsamonteria di Parma (on Via S. Pietro All’Orto not far from the cathedral), a multi-level cozy eatery with excellent choices throughout the menu; there is a sister establishment with the same name close to Castello Sforzesco; Risoelatte (on Via Manfredo Camperio half-way between the cathedral and the castle), with a grandma’s kitchen atmosphere full of vintage accessories and nice food all around; it also has a second location near Porta Ticinese; and Osteria della Lanterna (on Via Giuseppe Mercalli a bit off the beaten path), with a very non-modern take on the dining experience, where no English is spoken by the hosts, almost all the visitors speak perfect Italian, there are no menus and instead, before each course, you are verbally given a choice of two-three dishes (different sauces may increase the variety to five-six); you do not select the next course until you are finished with what is in front of you, which will be invariably tasty and reasonably simple.
The excellent train network makes Milan a very good base for further exploration of Northern Italy. Points in Lombardy and Piedmont (such as Bergamo, Torino, or Mantova) can easily be reached for day trips. Points in Emilia-Romagna and Veneto are similarly accessible if slightly further away. Even Venice is within reach. Lake Como is just an hour away, although you would probably need several days to enjoy that (and use a car rather than a train to get around).