Story by Cheryl Levitan

When I selected Milan as a travel topic many months ago, I never imagined that we would still be struggling through COVID. Regulations for travel are like sifting sand, and unpredictable restrictions don’t seem to be going away just yet.

With globetrotting a mainstay throughout my life, its absence has been discouraging. I wrote in past issues about rediscovering the streets outside our door while walking during lockdown, viewing old destinations with new eyes and exploring places that my husband and I might never had ventured to had we been able to reach far-flung locations. But I’ve discovered yet another positive to the current situation; the realization that there’s great value in just the act of booking a trip. Regardless of whether those journeys were eventually postponed or canceled, the research and virtual exploration was worthwhile in itself. Transcending everyday issues, becoming lost in another culture revived my interest in places and people far from home. Lesser-known gems were stumbled upon; potentially costly mistakes in destination or route were avoided. In the end, none of that research was wasted. 

Finding myself subconsciously “tuned into” a particular destination, references to it kept popping up in books, articles and TV programing. I finally became engaged in what we might do, not what we couldn’t. Mental health experts actually encourage planning for travel as a forward-thinking activity to improve mental health since anticipation of something positive increases optimism in the present. But choosing to wait by the sidelines until it’s clear that external forces will make a trip possible? That’s a guarantee that you’ll be staying home since flights and tours will then be full. And, finally? Going on this journey of the mind is, by far, the least expensive travel that you will ever undertake! 

There was something even more surprising discovered during these many months. As trip after trip was canceled or delayed, the disappointment experienced wasn’t nearly as great as expected and grew less each time. Having used a travel agent for our bookings, payments and airline miles were eventually all returned without much effort on our part. And those refunds? Just like cash shoved hurriedly into a pocket or purse and then forgotten; money spent so many months prior had ceased to exist. To have it back felt like a windfall. Time also proved that there was always another journey for the booking, often with added stops or features even more promising.

So whether or not you can get there today, Milan is the perfect future booking to shake off those lack-of-travel blues. As Italy’s second-largest city, it’s the country’s economic heart, home to the national stock exchange and filled with sustainable architecture, start-ups and technology. One of the four fashion capitals of the world (alongside London, New York and Paris), it’s also filled with history and art. With an area slightly smaller than Washington, D.C.,  this city is flat (despite its closeness to the Italian Dolomites and Alps). With all central city streets leading back to the Duomo (cathedral), it’s easy to walk around and difficult to get lost. Milan has a refreshing underlying energy to it as well. Unlike the whole of Italy, where family history and Italian birthplace define a person’s identity, the Milanese care more about an individual’s abilities and ideas.

What sets Milan apart:

The Duomo: The biggest cathedral in Italy and fourth-largest in the world, it is topped by an array of thin Gothic spires, statues and embellishments. Climbing up to walk across the roof of this huge sandcastle is surreal, and the view of the city and mountains beyond is sublime. Taking 600 years to complete, the Duomo sits in a large piazza that serves as a central meeting spot for everything and anything. That includes striking workers … but only on Fridays … and not when it rains. Followed by wine and music, we decided these strikes were as much about a day off as grievances.

Food: With 20 Michelin-starred restaurants in the city, Milan is also home to Apertivo — the original happy hour. Begun in the 1700s by King Vittorio Emanuele II, today it’s a ritual to meet after work for a glass of wine before dinner. But here, every glass of wine comes with a free assortment of food. We found Apertivo to be the perfect dinner. And unlike southern Italy (dry and warmer), where wheat, tomatoes and olive trees thrive and pasta and olive oil reign, northern Italy’s rain and grazing pastures bring risotto, meat and food cooked in butter to the table. We did have excellent pizza here, however, which vied for “best” honors with one we ate in Kyoto, Japan (go figure!).

Galleria Vittorio Emanuele II: Named after the first king of a unified Italy (Mr. Apertivo himself!), this is the oldest and most beautiful shopping center in Italy. Built in 1865 and located next to the Duomo, its magnificent glass roof, arches, mosaic floor tiles, frescoes and restaurants are so captivating that you might forget about shopping … well, almost. The Galleria is also home to the Leonardo3 Museum ( With models of his inventions and digitally restored paintings, we found this the best of the da Vinci museums.

Fashion: Milan’s love affair with fashion began in the 11th century, hitting a peak producing fine tailored fabrics for the elite of the Renaissance. When the post-World War II economy demanded higher end, ready-to-wear fashion for an emerging business class, Milan answered the need. Armani, Missoni, Versace, Prada, and Dolce and Gabbana (among others) are based here. The Galleria and Quad d’Oro district are the places for cutting-edge fashion (but check the price tags before you fall in love!). Confused by the sheer number of tall, young Milanese women with style, grace and composure, I found it even more disconcerting how little they consumed in restaurants (as I inhaled my meals). It soon registered that fashion week was just days away; these were international models (and no doubt quite hungry). 

Santa Maria delle Grazia: On the opposite side of the Duomo from the Galleria, this understated church houses a famous mural — The Last Supper by Leonardo Da Vinci. It was bombed by Allied forces in World War II, but this masterful psychological study of the moment when Christ reveals his own betrayal miraculously survived. 

Sforzesco Castle: The Sforza dynasty ruled Renaissance Milan and commissioned da Vinci to work there as an engineer, sculptor, painter and architect. This former 15th-century fortress today protects seven specialized museums and courtyards that host civic events and concerts.

Teatro Alla Scala: This is among the world’s most famous opera houses., The greatest singers of the last two centuries have performed here. If you can’t score a ticket, a visit to the adjacent museum grants a view of the theater.

Pinacoteca di Brera: One of Europe’s premier art museums, it’s located in one of the city’s most charming neighborhoods. Many of the artworks are accompanied by “sense” samples —  reproductions of the fabrics depicted or fragrances related to the images.

Porta Nuova: With state-of-the-art architecture, shopping, restaurants, nightlife, and a system of gardens, piazzas and bike paths that connect them all, this is an award-winning urban renewal project.

Lake Como: Just 1.5 hours away, it’s easy to plan a day trip here. A huge lake bordered by lovely villages and spectacular villas, it’s been a retreat for the wealthy since Roman times. Many celebrities own homes here (including George Clooney).

Intrigued by Milan? Book it!