Italy 2017 - Part 3 of 4: FLORENCE

This took a lot longer than I expected, but I had a lot of thoughts (and even a twist ending.)

So here’s a theory: Florence is Italy’s Greatest Hits album. 

It has all the big names: The House of Medici, Machiavelli, The Renaissance. You’ve experienced them a thousand times over, to the point where they’ve become part of the background radiation of modern culture. If there was a classic rock station for art and architecture, they’d be playing Florence 24/7 like it was Bohemian Rhapsody or Don’t Stop Believin.

But there’s a flip side (#OldMediaReference) to that analogy: the thing about Greatest Hits albums that makes them equally interesting and frustrating is that because they’re composed entirely of snippets in time, they’re not really complete albums in and of themselves.

Oh sure, obviously you can enjoy everything on a Greatest Hits album when you take them as singular experiences, but they’ll never really come together with the cohesion you’d expect from an entire album. They’ll always be slightly fragmented, with stylistic changes that reveal themselves as products of their specific moment of creative inception; never quite gelling into a singular whole.

Put more simply, no Greatest Hits album will ever feel as complete as Dark Side of the Moon, or My Kind of Blue, or To Pimp A Butterfly. They may be chock full of beautiful, meaningful, or culturally relevant snippets, but absent the context of time, place, and stylistic symmetry, they’ll always ultimately feel a little…shallow.


We came into Florence knowing it was almost everyone’s favorite city in Italy. When I asked for recommendations on things to do/see/eat in Italy, 95% of them (not an exaggeration, I just counted) were in or around Florence. A dozen times or so, I heard people say “Florence is my absolute favorite” or “it’s magical,” or “no city in Italy can match Florence” or something similar. So we had high expectations as the train pulled into the station and we clamored out onto the track alongside several hundred of our closest friends.

Navigating any city on foot and with luggage is difficult. Navigating any city on foot, with luggage, and in the rain is outright hard. Navigating Florence on foot, with luggage, in the rain, where your apartment is smack dab between the biggest outdoor market in the city (open rain or shine) and one of the biggest tourist destinations in the country - well that’s an exercise in personal murder restraint.

So we began our journey into Florence splashing through the puddles, trying to avoid sinking a wheel into a missing or uneven cobble, explaining - for the fifth time this block - that no I don’t need new luggage; as you can plainly see I have luggage. It’s right here. In my hand. Please get out of my way.

Fifteen minutes of rather terse urban navigation later, we reached our apartment, nearly tossing our suitcases as we crossed the threshold of the doorway just to be rid of them. After a quick overview of a very-not-to-scale paper map, we figured out that we were actually very ideally placed for the city. So doing our best to discard the negative energy we’d accumulated between the train station and the apartment, we ventured out into the great unknown to go get lost just as - as if by way of an apology - the city immediately pulled out sapphire blue skies and fluffy white clouds.

Let me be upfront: I … never really gelled with Florence. It was beautiful, and I’m genuinely glad we spent so much time there, but in many ways it felt so polished and so familiar that it just never really felt like a real city. The feeling I got walking around the city was that I could have very easily just been in a well-made theme park land. I also don’t think that feeling was helped by the fact that out of all the cities we visited in Italy, Florence was where I felt most surrounded (and at times, overwhelmed by) tourists, and the one where we heard near constant English somewhere around us.

And again, Florence is unquestionably gorgeous. I have easily 100 photos of, around, up, and on top of the Duomo. It’s a stunning piece of architecture and design, and we devoted three quarters of an entire day to just exploring its wonders. But after seeing Florence from Piazzale Michelangelo, and touring a half dozen choice tracks from its greatest hits catalogue, I still didn’t get any sense of the city itself. I knew what it *was* - that was made absolutely crystal clear all around you - but what I was searching for was some sense of what it *is*. Today. Right now. 

And the part that bothered me most about Florence is that I don’t think I ever found it.

Let me sequence break a bit here, and take a step back. My personal travel philosophy is that I tend to prefer semi-blind exploration over planning, and getting to know a city by its food and layout. I like to wander, and let a city and culture open themselves up to me - as opposed to seeking out elements that I’d bookmarked in advance. That sense of not knowing and then finding is more thrilling to me than checking off a previously-considered to-do list. Does this mean I sometimes miss the “can’t-miss” elements of a city? Absolutely. But it also means that I get a better sense of what the people who live there experience and find important, and have a thousand large and small adventures that are uniquely mine and almost irreplicable.

To be clear, I often have one or two things that I’m interested in experiencing, but I try to keep it to one planned or expected thing per day - such as a specific attraction or area of the city - with the rest of the day devoted to getting as thoroughly and properly lost as possible.

So when we were setting up the trip, I only had a couple specific things I wanted to do beyond “eat and drink my way through Italy.” Generally my unstated goal for each city was to find the most authentically “here” food experiences, to see the streets as its citizens do, and to do my best to discover what really and truly matters to that city.

So the irony (or personal hypocrisy?) of all of this is that for the four days we were in Florence, the food and wine were, without exception or equivocation, absolutely superb:

  • We had the best pasta I’ve ever had in my life in Florence - made by dumping freshly made, just cooked noodles into a wheel of Parmigiano-Reggiano, and then mixing the cheese and pasta up with an absurd amount of cream and freshly-shaved black truffle. 
  • I had the single largest steak I’ve ever eaten, at somewhere between two-and-a-quarter and two-and-a-half pounds, served perfectly crusted on the outside and just this side of raw in the middle - Florentine style.
  • We took a day trip out to Chianti and drank the best Italian wine I’ve ever had, and then went to the Tuscan Wine School the next day to surpass it again by discovering a dozen different ways to turn Sangiovese grapes into joy.

If you go beyond simple culinary hedonism, everything you’ve ever read about the architecture of Florence is, somehow - impossibly - actually understating it. 
For all my comments above, there’s a very good reason the Cathedral di Santa Maria del Fiore is one of the most visited cathedrals in Europe. Even today, standing in front of it, it seems absurd - like something CGI-ed into the background without thought or consideration to real world physics or historical technology. How does it…why does it…just…exist? Right there? Still? And we can go inside?

Turns out that goes doubly so for the inside, which defies all attempts to properly convey or communicate scale of size or effort. Suffice to say that whole lives were lived singularly devoted to the construction of this one building. Whole families. For generations. This singular structure was their entire purpose in life.

Pick a museum and start wandering through, and you’ll stumble on names that probably ring a bell such as Michelangelo, Botticelli, Caravaggio, or Da Vinci. They’re all there, because like First Avenue & 7th St Entry, they all got their start there. And then you find yourself standing in front of The Birth Of Venus, or Adoration Of The Magi, or Annunciation, or David. 

It’s surreal. And overwhelming. And humbling. 


Beth and I have talked about this a lot, but I came away feeling like Florence as a whole was so focused on highlighting portions of its past that I never got a sense of what it meant today, hundreds of years removed from its former glories. To continue the classic rock analogies, Florence felt like seeing The Rolling Stones live: no one’s shelling out to hear the new album, so everything is tailored toward making the experience about the familiar.

After a while, it felt a little like a video game: no matter where we went, we were pulled back into one very specific period of Florence’s past - like the developers were using an invisible hand to bring us back onto the gameplay path. We found ourselves in a cycle of tourism which, while perfectly comfortable, remarkably easy, and occasionally awe-inspiring, lacked the sense of adventure, or intrigue, or curiosity that Milan and Genoa provided. To steal from game design terminology a bit, in Milan and Genoa we discovered things, but in Florence I never felt like we had much agency.

Perhaps this feeling was why my favorite moments in Florence were the quiet ones: a post-dinner gelato and walking through a square at midnight. Hiking up to Michelangelo Park at sunset and gazing down at the city while the sky lit up purple and red. Pizza and people-watching on the upper level of the market. Everything about our day in Chianti. The quiet moments were the ones where I could feel like I was starting to appreciate the city and not just being moved through the “attraction -> shopping -> attraction” pathway.

So that leads to the big questions: 

Did I enjoy my four days in Tuscany? Yes (mostly.) It (obviously) wasn’t my favorite city of the trip, but it was still four days in a beautiful, historic city with incredible architecture, excellent food, and an almost endless supply of inexpensive but superlative wine.

Will I go back? I may; one day. I feel in many ways that I’m being unfair to the city. Perhaps I was too taken by Genoa, and judged Florence by an unfair set of expectations upon which it was never designed to compete. Perhaps that I owe it to the city to give it another chance. Perhaps, having done all the big attractions already, I can wander around with no destination in mind and finally find the connective tissue that makes the city more than just Renaissance Disneyland.

But as I write this out, now comfortably back in California, it strikes me that maybe I’m just …well, maybe I’m just wrong. Maybe, like standing in front of a Caravaggio and thinking “wow it’s…really dark” I’d focused on the wrong elements and missed the point entirely. Maybe the most important element of Florence’s identity today *actually is* that it forever reminds us of a very specific time.

The grand irony of Florence is that by celebrating its past so overtly, Florence stands as a demonstration to the modern world of what a place and its people can do when they deliberately choose to cast aside a slavish veneration of the past. That we can choose to reshape ourselves around comprehensive cultural progression. That even in the darkest of ages we can choose to pull whole civilizations forward towards renaissance and discovery. And there’s something beautiful to that sentiment.

Perhaps that’s what Florence is today: a timeless reminder that the moments in human history when we allow ourselves to dream and be driven by a sincere desire to explore and support artistic and intellectual creativity are the moments in human history when we build the great works that will forever define us.

And even if we’ve heard that refrain a thousand times before, maybe there are moments in human history where we need to be reminded of that, and hear it again as if for the first time.


Leaving Florence, we head off to the last stop on our journey: Rome. We’ll only have a few days here, so we won’t have much of a chance to really get to know it with any real amount of intimacy, but amongst the literal ruins of Western Civilization I’m hoping that we can at least get a glimpse of the city’s heart and soul. 

And maybe eat a cannoli.

Italy 2017 - Part 4 of 4: ROME

Italy 2017 - Part 2 of 4: GENOA