Lately, I seem to have Milan on my mind. To me, the Grey Lady is a dynamic city that propels you into modern Italy, setting itself apart from the Grand Tour allure of Rome, Florence, Venice and Naples. Milan never quite gets the standing ovation that I feel she deserves for her architectural and cultural legacy, design innovation and Italian history. With that, here’s how I enjoy a few days in Milan’s historic center.
Take Me To The Teatro
Opera buffs know that there is nothing quite like Teatro alla Scala, one of the world’s most famous opera houses where Madame Butterfly and Turandot premiered, among others, and where legends such as Maria Callas, Enrico Caruso, Luciano Pavarotti, Rudolf Nureyev and Carla Fracci called home.
Every year on December 7th, the celebration of Milan’s patron saint Sant’Ambrogio, the opera hosts its opening night, so expect to see the city’s most stylish come out in droves for Don Carlo, Turandot et al. Personally, I love catching a night at the Teatro alla Scala ballet with principal dancers Roberto Bollè and Nicoletta Manni, and dancer Denise Gazzo.
If there is no time for an opera or ballet, consider taking in some arias with Milan’s You Are Verdi, an immersive virtual-reality walking tour. I time-traveled to 1800s Milan through the eyes and music of composer Giuseppe Verdi. This untraditional peek at the past put me right into Verdi’s life and love for about two hours. If no time for Verdi, take an hour to walk through “Fantasmagoria Callas,” the Museo Teatrale alla Scala’s celebration of opera diva Callas done through works by artists such as Francesco Vezzoli, Latifa Echakhch and Giorgio Armani.
It’s Duomo Time
There’s a reason that a trip to Milano’s Duomo — Northern Italy’s most beautiful example of Gothic architecture — tops every visitor’s list. Book a private fast-track guided tour to see the ancient Baptistery of San Giovanni alle Fonti and the cathedral’s spires for an incredible rooftop view of modern-day Milan and then take a walk through Galleria Vittorio Emanuele II.
Milan’s Galleria is Italy’s oldest shopping center and has been the base of Milan’s social life since its opening in 1877. The neoclassical, four-story double arcade of glass and iron is known as il salotto di Milano (the living room of Milan), because it draws everyone in for its beautiful boutiques including Fratelli Prada, Prada’s progenitor from 1913. Look out for Osservatorio, Fondazione Prada’s experimental art exhibition space on the fifth and sixth floors.
Somewhere behind the Galleria is Boeucc, pushing 325 years. This is one of Italy’s oldest restaurants, so of course it must make the most perfect home-town dish cotoletta alla Milanese (Milanese-style veal cutlet). Located in the beautiful Piazza Belgioso- a beautiful neoclassical square near La Scala and the Galleria- Boeucc is also an architectural, art historylandmark. And you get it as soon as you walk it: high ceilings, Murano glass chandeliers, hardwood floors and marble columns. You are in peek Milan, so expect a strictly Milanese menu.
Bring Me Back to Brera
The crossroads of Italy’s art and fashion are the Quadrilatero D’Oro (the Golden Quadrilateral) and Brera, two Milan neighborhoods lined with incredible boutiques and eateries. The Golden Quad is boundaries by Via Sant’Andrea, Via Senato, Via Manzoni, and Via Monte Napoleone, four streets of pure Milanese chic.
The neighboring Brera art district is best known for charming cobblestone streets, fabulous shops, and a boho vibe. I’ve written a guide to the Brera neighborhood here, but in a nutshell, this is an art lover paradise for the Pinacoteca Brera, one of the world’s most spectacular collections of Italian paintings.
Cocktails at Camparino
There is never a time when I skip a stop at Camparino, the Galleria’s historic bar. Since Davide Campari opened the bar on Milan’s Galleria’s ground floor in 1915, Camparino has been the go-to destination for anyone and everyone. The historic Bar di Passo is original is design, style and cocktails.
White jacketed waiters serve Negronis, Campari Spritz, and Campari Seltz, the three benchmark cocktails. If you are something else, provided it’s Campari-based, go upstairs to Sala Spiritello, you’ll a futuristic mixology bar led by heralded bartender and Campari ambassador Tommaso Cecca. I’ve enjoyed some of the very best drinks of my life here, as well as pescholine, tiny peaches.
Off the record and in the subterranean is Camparino’s Sala Gaspare, a very private lounge which only hosts 12 guests with personal bartender. The lounge is dedicated to Davide’s father, Campari inventor Gaspare so of course Cecca tapped into Campari history for its menu. He sourced centuries-old cocktail books and menus to create a three-act menu which includes archival cocktails, Campari drinks and pre-batched recipes. The space is gorgeous, note the vintage Campari posters. bartender.
Modern Milan through Architecture
Milan’s architecture scene is way more than the Duomo and Castel Sforzesco. It’s an architecture lover’s escape from ancient, medieval and Renaissance to modern fetes of design. The historic center has some of Italy’s most important examples of 20th and 21st century architecture and design. From the palazzi of Marcello Piacentini to the skyscrapers of Gai Aulenti, Milan is an incredible landscape of great architecture. Full disclosure: I am a big Piero Portaluppi fan.
Sign up for a modern tour architecture with Context Travel. The architect-led walk takes you through the layers of the city’s design history, from the medieval fortress to the present-day metropolis and show off genres such as Novecentismo, Rationalism, Neoclassical and the works of architects Portaluppi, Piacientin, Ponti, BBPR and more. For full focus on Portaluppi (aka the master of modern Milan), visit Fondazione Piero Portaluppi and set up an afternoon walking tour of his most famous projects.
Inside Parco Sempione is the Triennale, Milan’s museum of art and design. The attraction is also home to the unparalleled Museo del Design Italiano, an essential collection of influential works from Italian designers over the past century. This museum is vital to understanding the innovative history of Milan and Italian creativity. Plan lunch at the museum’s garden café or its breathtaking terrace restaurant.
Where To Stay
If Milan is the Grey Lady, then Grand Hotel et de Milan is the city’s Grand Dame. There is no place more epicentre and nor historically poignant than this hotel. Since its 1863 opening, the Grand Hotel et de Milan has been a destination for opera luminaries including like Giuseppe Verdi (who made it his home in 1872), Maria Callas, Rudolf Nureyev, and of course stage enthusiasts and global glitterati.
I stayed in the Gabriele D’Annuzio (named for the early 20th century Italian poet) suite, a corner on the third floor that couldn’t have felt more romantic. All 72 rooms and suites are adorned in an 18th-century aesthetic with a 21st century flair by Milan’s DimoreStudio. Rich fabrics, period furniture and historic art work cleverly blend with Dimmer’s contemporary touch. This is Milan grandeur at its best, and it helps that its Via Manzoni address in the Quadrilatero d’Oro immerses visitors in historic Milan. Gerry’s Bar is a must-visit during fashion week and Don Carlos Restaurant is a post-La Traviataindulgence.
For another center address, Four Seasons Hotel Milano is a great escape. Taking a cue from the hotel’s original incarnation as a 15th-century convent, the 118 rooms and suites exude Old World charm with frescoes, stone accents and vaulted ceilings, while a location on Via Gesù places guests in the center of the fashion quad, making it an ideal location for those looking to fill their suitcases with the season’s latest designs. Stilla Garden is one of the best spots for cocktails while their spa is an oasis.
A version of this article appeared in Forbes Travel Guide, January 2024.