1. Duomo di Milano

Milan’s magnificent Gothic cathedral took nearly six centuries to complete and features 3,400 statues and 135 spires.

Insider Tip: Skip the front entrance lines by booking rooftop access tickets online. Visit around 8:30am on weekdays for the best light for photography and significantly fewer tourists. The northeastern corner of the rooftop offers the most stunning and least photographed perspective of the spires.

2. Galleria Vittorio Emanuele II

One of the world’s oldest shopping malls, this elegant 19th-century arcade connects Piazza del Duomo to La Scala.

Insider Tip: While most visitors focus on the luxury shops, look up to appreciate the stunning glass dome. For an affordable experience, visit Camparino, the historic bar dating back to 1915, and stand at the bar like locals do for an aperitivo at half the price of sitting down.

3. Teatro alla Scala

Italy’s premier opera house has hosted world premieres by Verdi, Puccini, and other masters since 1778.

Insider Tip: Skip expensive show tickets and visit the museum in the morning, which sometimes allows peeks into the theater during rehearsals. Alternatively, purchase last-minute “loggione” (gallery) tickets for as little as €15 by queuing at the box office two hours before performances.

4. Castello Sforzesco

This imposing Renaissance fortress houses several museums featuring Michelangelo’s final sculpture.

Insider Tip: The castle is free to enter after 4:30pm on Tuesdays. Visit the often-overlooked Sala delle Asse with Leonardo da Vinci’s ceiling frescos, and afterward, enjoy the Sempione Park behind the castle where locals exercise and relax.

5. Pinacoteca di Brera

Milan’s premier art gallery with works by Raphael, Caravaggio, and Mantegna.

Insider Tip: Visit on the third Thursday evening of each month when the museum stays open until 10:30pm with reduced entry fees. Start from the top floor and work down, against the usual visitor flow. Don’t miss the hidden botanical garden accessible through a small door in Room 24.

6. The Last Supper (Cenacolo Vinciano)

Leonardo da Vinci’s masterpiece in the refectory of Santa Maria delle Grazie.

Insider Tip: Tickets sell out months in advance, but tour operators often return unsold tickets – check online at 5pm the day before for sudden availability. Or visit the church itself (free entry) and then try the “no reservation” line around 4:30pm when sometimes there are last-minute cancellations.

7. Navigli District

Milan’s charming canal district filled with restaurants, bars, and boutiques.

Insider Tip: Skip the overpriced canalside restaurants and explore the side streets like Via Corsico for authentic Milanese fare. Visit during the last Sunday of the month when the famous antiques market fills the streets, or go at 6pm on weekdays for aperitivo culture without the weekend crowds.

8. Bosco Verticale (Vertical Forest)

Award-winning residential towers covered with over 900 trees and 20,000 plants.

Insider Tip: While you can’t enter the buildings unless you’re a resident, the best viewing spot isn’t from below but from the elevated walkway in Biblioteca degli Alberi park. Visit at sunset when the golden light hits the greenery and the building’s maintenance team sometimes waters the plants, creating a misty, magical effect.

9. Cimitero Monumentale

An open-air museum of sculptures and architectural masterpieces dating back to 1866.

Insider Tip: Request a free map at the entrance and seek out the tomb of the Campari family with its striking Last Supper bas-relief. The cemetery offers free guided tours in English on the first Sunday of each month, revealing stories about Milan’s historical figures that you won’t find in guidebooks.

10. Quadrilatero della Moda

Milan’s famous fashion district with flagship stores of Italian and international designers.

Insider Tip: Skip shopping altogether and visit Palazzo Morando on Via Sant’Andrea, a little-known museum of Milan’s history with period rooms and historical costumes. Alternatively, explore the publicly accessible courtyards of historic palazzos along Via Monte Napoleone, especially numbers 2 and 12, for Instagram-worthy photos without spending a euro.