The Timeless Charm of Florence: Reflections On Five Decades of Travel
Summary: Fifty years after first visiting Florence as a budget-conscious college student sleeping on university floors, contributor Ali Webb returns at age 69 to experience the city with a slower tempo and modern comforts. Staying at boutique hotels like Palazzo Castri 1874 and Ville sull’Arno provided a quiet, relaxing base to explore familiar sights. This return trip traded frantic sightseeing for simple pleasures: making pasta in a cooking class, sipping wine from historical wine windows, and relaxing over coffee in bustling piazzas—proving that returning to a beloved destination offers a deeper, altered perspective.
My first visit to Florence came more than fifty years ago as a junior in college, traveling through Italy on a student budget. Florence in the 1970s was a city of crowded trains, inexpensive wine, and sleeping on the floor with friends at their university housing.
Days were spent wandering narrow Renaissance streets with little more than a guidebook and enough lire for coffee, pizza, and museum admissions and wine, of course.
Like many travelers discovering Florence for the first time, the city felt impossibly old, cultured and dramatic. The Piazza della Signoria appeared exactly as art history books had promised. The Duomo dominated the skyline. Tiny cups of espresso fueled a short, packed visit trying to fit in an entire city. That was then; this is now.
Over the decades, Florence has been a city that I have visited at different stages of life: once with a four-year-old child more interested in pigeons, pasta, and gelato than in Renaissance masterpieces; later, with a young professional daughter experiencing Italy and sharing our love of wine (and pasta); now, fifty years after that first visit, as a 69-year-old traveler who has both the time and the budget to experience a more comfortable Florence. It was good to be back.
A Different Kind of Florence Stay
This time, the visit began at Palazzo Castri 1874, a boutique hotel that combines a historic Florentine building with contemporary comforts. Its location makes it particularly convenient for exploring the heart of the city on foot. It also offers a wonderful tub, swimming pool, and spa to wash away jet lag.
Nearby, the Mercato Centrale offers another Florence experience. The historic market remains a place to browse, with meats, cheeses, produce, breads, and other Tuscan specialties, while the upstairs food hall provides an easy way to sample a variety of Italian foods without committing to a long restaurant meal.
It is Florence with crowded tables, glasses of wine, pizza, pasta, and plenty of opportunities to watch people come and go. It’s also a great place to pick up food souvenirs.
Later, the trip shifted to Ville sull’Arno, a five-star hotel overlooking the river. Fifty years earlier, Florence meant sleeping on a floor. Now it meant a comfortable room, a quiet retreat from the crowds, and the pleasure of returning to the hotel along the Arno at the end of the day.
That is the value and the gift of returning to a favorite destination over a lifetime. A place can remain familiar, while the way it is experienced changes completely.
Some Things Haven’t Changed
Fortunately, not everything about Florence has become expensive or polished. The trains are still cheap. So is the wine.
There remains something wonderfully democratic about traveling through Italy by rail, stepping off a train in the center of Florence, and discovering that a good glass of wine or a simple pizza can still be surprisingly affordable.
Some things never change, for example the gelato shop at the base of the Ponte Vecchio. Fifty years later, it was still there—and the gelato was still delicious. In a city filled with new restaurants, boutiques, and tourists photographing almost everything they eat, finding a small pleasure remembered from decades earlier offered reassurance that some pieces of Florence have survived. And, of course, there are the ubiquitous leather shops, where one can find purses, wallets, belts, and backpacks in all sizes and colors.
The great museums and landmarks provide an even stronger sense of permanence.
The Uffizi Gallery still draws visitors into its corridors to stand before Botticelli, Michelangelo, Leonardo da Vinci, and other masters. Despite timed tickets, security lines, and much larger crowds, encountering works seen countless times in books remains extraordinary.
The Bargello National Museum, by contrast, offers a quieter encounter with Renaissance Florence. Its stone courtyard and sculpture-filled rooms seem to stand outside modern time. Walking through the museum today, it is easy to imagine a student traveler from fifty years ago wandering through the same rooms. Another stop, at the Palazzo Medici Riccardi, yielded the spectacular ceiling painted by Luca Giordano, the celebrated Neapolitan Baroque painter. So many museums; so little time!
And then there is the Duomo. No matter how many photographs have been taken of Brunelleschi’s dome, turning a corner and suddenly encountering the cathedral’s enormous red-tiled dome and intricate marble façade remains one of Florence’s great experiences. Some landmarks become less impressive with familiarity. The Duomo does not.
Rediscovering Florence Through Food
Food offered another way to experience the city beyond simply eating in a restaurant.
A cooking class at Ristorante Rosso Crudo had us laughing as we made ravioli and thick pasta. Making pasta by hand, learning the techniques behind tiramisu, and sharing the results over generous amounts of Italian wine—all was best shared around a long table with people who started as strangers and became fellow travelers.
During our trip, we also returned to Cibrèo Ristorante, which we had enjoyed on an earlier visit. The pleasure comes not only from the food but also from discovering that the restaurant started by the famed chef Fabio Picchi has thrived.
And then there was the giant slab of Florentine steak at Regina Bisteca, an amazing spot for an extraordinary meal. Other meals were intentionally simpler: pizza, pasta, sandwiches, coffee and, inevitably, more gelato.
Coffee, Piazzas, and Wine Windows
Florence also rewards travelers willing to do very little.
Coffee in the city’s piazzas became a daily ritual. Rather than rushing from one attraction to another, there was time to sit with a cappuccino or espresso and watch Florence move around the table.
One could also stand and enjoy the city’s revived wine windows, or buchette del vino, which added another link between Florence’s past and present. These tiny openings in the walls of centuries-old palazzi were historically used to sell wine directly from noble families’ cellars.
Today, a number have returned to use, allowing visitors to order a glass of wine through a small stone window. We stopped at one in front of the restaurant that later hosted our cooking class. The wine window could easily feel like a tourist gimmick. Instead, it is strangely charming: an old Florentine custom finding a place in a city now crowded with 21st-century visitors.
A City That Rewards Returning
Age changes the rhythm of travel. Younger travelers often rush to see everything possible, measuring a trip by landmarks conquered and museums completed. Age requires a different tempo.
Stopping for another coffee in a piazza, another glass of wine, a leisurely walk beside the Arno, or an afternoon when seeing only one museum is more than enough.
That may be one reason Florence is particularly rewarding as a repeat destination. It does not require constant sightseeing to justify the visit. Its pleasures are found as easily at the Mercato Centrale or at a wine window as inside the Uffizi.
A first visit to Florence may be dominated by a checklist: the Duomo, Uffizi, Ponte Vecchio, David, Bargello. A return visit grants permission to tear up the checklist.
Fifty years transform both a city and a traveler. Florence now has online museum reservations and crowds carrying smartphones instead of guidebooks. Yet inexpensive trains still arrive at Santa Maria Novella. Affordable wine is still poured. Coffee is still best enjoyed sitting in a piazza. The Duomo still stops visitors in their tracks. The Uffizi and Bargello seem to stand as though no time has passed.
And at the foot of the Ponte Vecchio, there is still gelato.
Sometimes the greatest pleasure in returning to a place is discovering not how much has changed, but how much hasn’t.
*Contributor Ali Webb, PhD is adjunct faculty at the University of Michigan and Columbia University. Her long career in strategic communications has offered her many opportunities for domestic and foreign travel. She wrote a bi-monthly Sunday travel column, The Indulgent Traveler, for a Gannett daily in Michigan and now contributes to other travel websites.
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