For the past ten years, I’ve passed through Bologna several times on my way home to Florence. Each visit revealed a new layer, a new reason to fall in love with this city. Today I brought Olivia with me — she’s flying back to the States tomorrow — and we had one full day to explore this vibrant historic and gastronomic heart of Italy.
Bologna is the perfect city to lose yourself in: its elegant architecture, medieval side streets, bustling food markets, weathered facades, and iconic towers create a tapestry of stories waiting to be discovered. It’s compact and easy to navigate — something I mentioned to Olivia, who immediately switched on her step counter to see if today would beat her Barcelona or Rome records.
Our first stop was Piazza Maggiore, the medieval heart of the city. Dating back to the 1200s, the square evolved over centuries and today is lined with palaces, churches, and a few delightful secrets. One such secret sits beneath the vaulted arches of the Palazzo del Podestà: if one person stands in a corner facing the column and another stands diagonally opposite, you can hear each other’s whisper perfectly. Olivia tested it — and her surprised laugh echoed softly through the arches.
Just beside the square stands the Basilica of San Petronio, the sixth-largest church in Europe. Its unfinished façade hides a magnificent interior, including a breathtaking meridian line on the floor and the Chapel of the Magi with its beautiful fresco cycle.
Bologna’s soul is made of flavors: tortellini, tagliatelle, mortadella, and crescentine. Naturally, we couldn’t miss the Quadrilatero — the city’s ancient market district, once home to medieval guilds. If you ever find yourself here without a guide, simply type “Mercato di Mezzo” into Google Maps and wander the surrounding streets. Cured meats, fresh pasta, fish stalls, flowers, fruits, vegetables — a colorful, fragrant celebration of Emilia-Romagna’s culinary heritage.
Bologna is known by three nicknames:
La Rossa – The Red: referring to the warm terracotta hues of its buildings and its historical political identity.
La Dotta – The Learned: home to Europe’s oldest university, still alive with more than 85,000 students.
La Grassa – The Fat: a tribute to its world-famous cuisine (and also to its love affair with fast cars — Ferrari, Lamborghini, Maserati, Ducati all hail from Emilia-Romagna).
After a perfect coffee, we continued toward the University of Bologna, founded in 1088 and considered the oldest in the world. Over the centuries, many buildings were added to host academic lectures, but none are as compelling as the Archiginnasio. Commissioned by Cardinal Borromeo in the 16th century, it once housed the university’s law and humanities departments. Inside, a courtyard with thirty arches and vivid frescoes leads to the famous Teatro Anatomico — a 17th-century wooden anatomical theatre where the first anatomy lessons were taught.
Walking beneath Bologna’s iconic porticoes, we reached the city’s most recognizable symbols: the Two Towers, Asinelli and Garisenda, medieval expressions of family prestige. A local legend tells of a farmer who discovered a chest of coins and jewels while working his fields. He kept the treasure secret until his son fell in love with a noble girl. The girl’s father agreed to the marriage only if the young man built the tallest tower in the city. Using the hidden treasure, the son built the Torre degli Asinelli — rising more than 95 meters. She said yes.
The tower is open to visitors, though its 498 steps require determination. Bologna once had hundreds of towers, much like San Gimignano; today, 22 remain.
The city is also home to the world’s longest portico system — over 53 km of covered walkways. The most famous is the Portico di San Luca. Stretching 3.5 km with 666 arches, it once served as a pilgrimage route connecting the city center to the hilltop Sanctuary of the Madonna di San Luca. Walking it is a quintessential Bolognese experience.
When we finally reached the sanctuary, Olivia proudly announced that we had broken her step record — and I quietly avoided mentioning that we still had the return walk ahead of us. And of course, having come all this way, we couldn’t skip the additional 110 steps up to the dome for the San Luca Sky Experience, offering a 180-degree view over Bologna and its surrounding hills.
By late afternoon the sky dimmed, and the Christmas market lights began to shimmer — the gentle signal that evening was approaching. We said our goodbyes: we laughed, cried, held each other close. This day felt like the perfect ending to the past month we had shared.
As the city softened into evening light, it felt as though Bologna itself was saying goodbye with us. Looking back from the hilltop, every step, every discovery, every shared moment blended into one warm, lingering memory. I knew this day was more than sightseeing — it was the essence of our time together, something that grows more precious as life pulls us in different directions.
When we hugged, I felt both gratitude and a tender sadness. Gratitude that she was here with me, and sadness because every farewell carries a quiet ache. Yet I was certain of one thing: we both carry this day with us. She takes it back to the United States; I take it home to Florence.
And when we meet again, this day will return to us — the mist, the hill, the 666 arches, the tired legs, the laughter, and that quiet kind of love that doesn’t need to be spoken, only felt.