The transfer to Milan’s metro was effortless, and stepping off at the Duomo stop was nothing short of jaw-dropping.  Emerging from the underground, I looked up to find Milan’s cathedral towering directly in front of me as the stairs end literally in the Duomo square.  The city buzzed with energy from tourists snapping photos to street performers entertaining passersby, and the unmistakable excitement of being somewhere special.

After a few quick photos, I made my way to the hotel to unpack.  While it appears small, the mattress was very comfortable and the breakfast excellent.

Day 1: A Culinary Adventure

Un'avventura Culinaria

Though it felt late by U.S. standards, Milan was just getting started, so I headed out in search of dinner, especially with an early-morning walking tour waiting for me the next day.  I love to eat where the locals eat, so I followed the students to nearby Pizzeria Piz for pizza, tiramisu, and a glass of red wine.  The menu is delightfully simple with just three choices: margherita, white, or surprise.  Naturally, I chose the surprise, a chef’s choice pizza that is never the same twice!

The Canadians at the table next to me were debating the same gamble and watched my order arrive with hopeful curiosity.  When they asked what I had chosen, I offered to swap slices and just like that, strangers became companions.  Over shared pizza and easy conversation, we enjoyed one of those small, memorable travel moments that reminds you food is not just nourishment, it is a bridge.  Before parting, we toasted to each other's adventures with a complimentary limoncello; the perfect end to an adventurous day.

Day 2: Sforza Castle

Castello Sforzesco

When I return to Milan, I will make time to revisit Sforza Castle for a more in-depth exploration.  Our walking tour offered a helpful introduction, but my own preparations for the Heart of Italy tour—and a deep dive into the Medici era—had already given me a richer sense of its significance.  The Sforza family ruled Milan for generations, wielding formidable military and political power that made them anything but easy to challenge.

Built in the 15th century atop the remains of an earlier 14th-century fortification, the castle evolved from ancient Roman defenses into a Renaissance stronghold.  Over the centuries, it has worn many hats: fortress, ducal residence, symbol of power.  Today, the castle houses several impressive museums and art collections.  Milan itself was once a capital of the Roman Empire, adding yet another layer to the site’s long and complex history.

Artists including Leonardo da Vinci left their mark here, frescoing rooms that once hosted the city’s elite.  Standing in the vast central courtyard, it is easy to let your imagination wander: armored knights drilling on horseback, squires learning the art of war, and the ever-present sounds and smells of a heavily garrisoned castle buzzing with daily life.

Day 2: Street Photography

Fotografia di Strada

While I may live in a rural setting, I love getting swept up in the hustle and bustle to feel the true pulse of a city.  Milan does not disappoint.  One moment you are discovering a hidden medieval garden, the next you are navigating efficient public transportation or braving a perilous street crossing with locals who seem to do it by instinct alone.  Everywhere you look, history peeks out between modern life while displaying layered, lived-in, and endlessly fascinating character.  I could only imagine the delight experienced by those attending the 2026 winter Olympics in a few months!

Day 2: Galleria Vittorio Emanuele II

Galleria Vittorio Emanuele II

This grand shopping arcade virtually shouts high-end fashion from every corner and is a feast for the eyes.  One hat shop in particular caught my attention, though I knew it would have to wait for another visit; perhaps the next time I return for an opera at La Scala.

At the center of the gallery, visitors happily took turns spinning three times on their right heel atop the mosaic coat of arms set into the floor, each rotation gleefully counted out by onlookers. It is a small ritual, but one that adds a sense of shared delight to the space.

Despite being built of glass, steel, and marble, the structure surprisingly absorbs sound, creating a calm, almost hushed atmosphere beneath its soaring dome.  Judging by the animated chatter, a few fashionistas in our group were already plotting a return visit—credit cards at the ready.  Our guide played a game of Milan, Florence, or Rome for a number of fashion houses.  While not one to dress for trends but instead focus on timeless pieces, I had the highest rate of right answers (though he did surprise me with a few!).

Day 2: La Scala Square

Piazza della Scala

La Scala is a building you might easily pass on Milan’s streets without a second glance, as its understated exterior blends seamlessly into the surrounding architecture.  Step inside the story, though, and you are at the epicenter of the opera world.  Opened in 1778 on the former site of Santa Maria della Scala (which gave the theater its name), this legendary house has hosted premieres and performances by Toscanini, Verdi, Puccini, and countless others, setting a gold standard for operatic excellence.  Our local guide shared a bit of operatic lore: Milan, it’s said, has never forgiven Luciano Pavarotti for his voice cracking on a high B during Verdi’s Don Carlos here in 1996.  

As we ended the tour at this location, anticipation was already building for my own evening at La Scala.  Just across the street, a graceful square offered a quieter scene: a statue of Leonardo da Vinci surrounded by locals resting on benches, chatting with friends and family beneath trees glowing with autumn color—an everyday Milanese moment set in the shadow of extraordinary history.

Day 2: Pinacoteca Ambrosiana

Milan's Oldest Museum

Milan's oldest museum, Pinacoteca Ambrosiana, was just a half-block from my hotel, and with a bit of time between visiting the Duomo and that evening’s opera, I knew it was too close and too compelling to skip.  Home to an impressive collection of Titians and the world’s largest holdings of Leonardo da Vinci’s works (primarily his notebooks, sketches, inventions, and mathematical studies), it was an easy choice to squeeze in a visit.

There were no English guided tours available, so I relied on the audio guide instead.  The museum was pleasantly quiet in the afternoon, allowing for unhurried wandering.  I was grateful for the mild weather, as the building is not temperature-controlled beyond the final large room.  Once again, I found myself standing just inches from masterpieces, quietly awed by how these works have endured and continuing to inspire centuries after their creation.

Day 2: La Scala

Rigoletto

While I grew up listening to and performing classical music, opera was not a regular part of my early repertoire.  That changed in college, when I discovered a deep love for it and held season tickets to a local opera house for several years.  One opera in particular captured my heart: Rigoletto.  There is something about the Italian composers—the drama, the emotion, the sheer musicality—that lifts my spirits and keeps me perched at the edge of my seat from curtain to final bow.

How could I visit Milan—the epicenter of the opera world—and not attend a performance?  I packed my lightweight silk dress once again and made my way to La Scala, where I met several fellow travelers from the U.S. who had just finished Rick Steves Europe tours elsewhere.  It was a joy to connect with such like-minded travelers in a place that celebrates shared passions so fully.

The interior of La Scala is stunning, and the seats are surprisingly comfortable.  One feature I had never experienced before was the individual translation screen built into the back of each seat, offering multiple language options.  I chose English, though I found I understood much of the Italian being sung, which made my heart sing in return.

The performance was flawless, as it must be in a house that forgives no mistakes.  My local guide had earlier shared the story that Milan still recounts with collective horror: Luciano Pavarotti’s voice cracking on a high B during Verdi’s Don Carlos in 1992, followed by boos at the curtain call—an event that effectively ended his operatic career here and nudged him fully into the world of pop opera and the creation of the Three Tenors.  Sitting in that legendary hall, listening to Rigoletto unfold, I felt the weight of that history—and the thrill of being in this monumental theater.