Over my spring break I had $1,000 dollars of flight credit to use, built up from four postponed trips. After so many false starts, it was time to go again – and go I have. First up, Siena for the Strade Bianche. For the trip, I put away my Instagram and my updates and I turned to my journal. Over dinners and downtime, I wrote down my sensations. These are the moments that captured the trip for me, and I hope you enjoy the “crudo” distillation of my week in Tuscany!
March 3, 2022 — Firenze Centrale, Florence, Tuscany
People seem to flow here. In scarfs, overcoats, down puffers, and other regal regalia built for temperatures colder than now, the Italian masses move with effortless intention. In twos, and threes, and four, and sometimes ones but nearly never fives, people would come, and people would go in a swirl of the sing-song language of the land.
On the screen in front of a scattered queue were the gates for the trains around the Tuscan countryside. With trains coming and going every minute of the afternoon, the suspense in the ten minutes before departure grows as the space for the gate remains ominously blank. In Milano Centrale, I didn’t know this process and bumbled around the platforms trying to find information that had yet to exist. In Florence I was ready, cappuccino in hand, for the mad dash.
15:55 To Siena – Platform 3.
When the number flashed, the crowd around me ruptured. Unbeknownst to me, half of those around were peers, waiting for the same unknown platform. A moment of camaraderie in a country of strangers. Today, I have been the interloper.
Sure, there are probably other visitors around me, flowing with the locals. But to me, it’s all foreign. I do my best to fade into the background with my sleek grey suede shoes, black turtleneck, and flowing locks of brown hair. Nonetheless, before the end of the word Bonasera leaves my lips, my cover is blown. I just don’t quite flow.
Alas, what a lovely way to be foreign.
March 4, 2022 – Monte Saint Marie, Siena, Tuscany
Tuscany is wonderful.
Okay, now that we have out of the way, let’s get down to business. Today, I slept till noon. 10 to 12. Fourteen hours. Ugh, I feel like some kind of slovenly college kid. I cannot tell you the last time I voluntarily slept more than nine hours. It just doesn’t happen. Yet, I am on vacation, my body is confused, I hate planes and trains make me sleepy. So, I think I am going to give myself a pass because I missed nothing. There is literally nothing I must do, only things I want to do.
On the top of the lists of wants was riding. With the planes, trains and automobiles of the two days gave me some lovely scenes, I was in Siena for one reason: Il Strade Bianche – where road cycling meets the gravel world. The men’s and women’s world class fields will set off on their loop around the white roads of southern Tuscany tomorrow, but today was my day to demystify the iconic last 50 kilometers.
In the serendipity that comes from my tardiness, I hit the glorious sections in the bronzing light of the evening sun. Around me, the green fledgling shoots of Tuscan wheat rippled under a sweeping breeze. The soft blue of the sky only broken by the faint yellow of meandering clouds. And of course, the roads white as the name suggests: bianche.
Those gentile ridge lines and sinewy lanes underscore the ancient harmony of Tuscany. Both man and nature seem meticulously weaved together, even in some of the messy scenes of disrepair. There is a nonchalant artistry everywhere, the land wearing the thousands of years of humanity like the splendid worn coats of the Italian who call Siena home.
Wherever I went, over the hills and dales was Siena, peering through the haze, the old seat of a micro-empire. At its peak, the city on a hill was marked by the center tower of the Piazza del Campo. Like a pushpin on a wall map, I could never be lost in this all so foreign place.
March 5, 2022 – Colle Pinzuto, Siena, Tuscany
Warning: This is where I am going to go on a bit about bike racing.
I am not, however, going to provide some deep analysis of either race. After all, I somehow managed to see 0% of the women’s race despite trying very hard. No, I only learned of the race’s minutia after Pogacar arrived in the Piazza del Campo, when I watched the replay of the race in my humble shared Airbnb. For me, it was all about the feeling of it all.
For the TV viewer, the men’s race was probably boring. Compared to the generous showdowns of past Strade, this year seemed inevitable. The favorite, the boy king as some say, blitzed everyone. With shades of the greatest of all time, Pogacar did what have never been done before. For the last 50 kilometers, one third of the race, the king had no company. He had flown. The suspense evaporated from the minds of any TV viewer who had seen the previous years tour.
But on the ground, even with that same knowledge in our collective conscious, the race remained surreal. We lived the race in moments. Snippets. Seconds at a time, flying by us in a cloud of dust and desire. Moments some try to savor with phone cameras, both saving and spoiling the moment forever. It’s the paradox of the tifosi.
On the penultimate dirt sector where I found the riders out on course, I ignored my phone. I know there would be camera’s galore, and I would be remised if I was another dude with a phone captured by the HD-television showing my brother across the globe what was right in-front of my eyes.
I gambled. I wanted to welcome this boy king myself and in live in that chaos while it reigned in those few fleeting seconds. Thirty minutes later in the Piazza del Campo, the phone won out. It was just too spectacular not to take a souvenir. But on the dirt, I needed to be with the dust and in one of those moments that I know I soon won’t forget.
March 6, 2022 – Le Tolfe, Siena, Tuscany
While Strade had left Saturday night, I woke up Sunday morning with the barriers back and cyclists sprawling across Siena’s center. It was Gran Fondo day, and the everyman was king.
For all the men and women who raced on Saturday who looked cut from stone, Sunday was for the men and women – the legendary tifosi who would strive to finish Il Strade not just for the personal glory, but for the affinity for the gladiators flying through the day before. On my ride to the nearby Monte Lecce, I came by many some of the folks on the Le Tolfe climb. On the slopes where the legendary Matthieu Van Der Poel went thermonuclear the year before, the masses strained, groaned, and waddled their way to the top.
They rode mountain bikes, gravel bikes, road bikes, clunkers, Italian Stallions, and the vintage rigs you only see in places that abide by decades and decades of cycling lore and craftsmanship. Il Strade is a weekend, not a day, and that’s what makes it lovely.
March 7, 2022 – Piazza Del Campo, Siena, Tuscany
I already miss the murmur of the Piazza.
Every night as I venture from my Air bnb tucked away off the square, I am greeted by that pleasant hum of thousands of lively dinners, amplified by the towering walls of brick and the bowl of Siena’s center. The power of the Italian dinner is clear, as the restaurants all the way around are filled with Italian conversations over Chianti wines, cured hams, cheeses, and steaks of Toscana.
I shouldn’t be blinded by my week in Siena. I have been, for most of my days, behind the fortified walls of Siena’s past – walls that fended off medieval invaders and even the spread of Christianity itself. With the walls standing high even with the modern fillings, Siena remains marooned in its wonderful insularity.
With that insularity comes a lack of context for me, the traveler. All my generalizations of Italy are from the Italy that chooses to come in from beyond the walls. Yet, today my context grew. I ventured out to Montalcino and the stretches of the furthers southern stretches of the former Siena empire. In that little trip, the intricacies of Italy became clear.
While Siena is a city on a hill, Montalcino is a town on a mountain. Flanked on one side by some of the richest vineyards in all of Italy, and on the other by the low canopies of a Mediterranean forest, Montalcino puts Siena to shame in terms of geographic structure. Montalcino, in the face of this dominant geography, is restrained. Nonetheless, what Montalcino lacks in Piazza’s, Duomos and other medieval things, it makes up for in the wide swath of hinterland it peers over.
In Montalcino, during a far to brief pitstop, I realized just how much Italy had up its sleeve. Tucked away in every corner of a country with seemingly infinite crevasses is life that is as unique as the last. For me, that was the murmur of Siena, and even that seems still mysterious after 5 days beyond the walls.
March 8, 2022 – Centrale, Milan, Lombardy
I have been in Milan for two hours and I have seen a car crash, a many thousands person march and a very small person on a bike, all before I found a reasonably priced Italian restaurant. That’s just the way the news goes sometimes.
In all this mayhem I was back into life that felt digestible. Gone was the idyllic architecture, in was the cross-pollinating world of the cosmopolitan world. Milan is, after all, one of those big cities with big billboards and big windowed building that would only feel a bit out of place on the eastern seaboard. Albeit with less cyclists dressed in the styles of a fashion capital.
It’s a fitting transition to the red mud roads of Oklahoma where I am venturing next. Reflecting on my stint in Italy has given me a lot of joy in what I have stumbled upon. Every time I plan one of these solo journeys, I have a little thought, a little nag, that this will be the trip I get lonely. That part of me was sure I was going to feel marooned behind those Sienese walls. I should remember how that part of me is almost never right.
Traveling alone is ultimately a thrill. No safety valve, no comfort companion. Just a solo stranger seeing what comes. Serendipity is essential and everyone is a potential spur on your journey. For those who are introverts, it’s a beautiful chance to speak. For those who are extroverts, it will let you listen. For everyone, it’s always a lesson.
For as long as my memory serves, I. have pedaled bikes around my hometowns in American, imagining the streets were just like Italy. The closer the place resembled my fractured, make-believe Italy, the more it inspired me. Italy had been the archetype. Orchards were just like those found in the boot heal. Every time I found a tight switchback on a center-line-less road, I was just one more twist away from the base of the Stelvio or the Gavia. And of course, with every dusty gravel track through a verdant field, I was transported right to those strade bianche of Tuscany.
It turns out, my imagination wasn’t far a field. Sure, Staunton, Virginia, doesn’t have the castles on every surrounding knoll. Richmond’s flood walls are not for medieval invaders. While the orchards on the ridges of Charlottesville are not home to olives, oranges and the other goods of the Mediterranean bread basket. But these things, these placers and these sensations are far closer than they seem. Joyful things are joyful things, and slight contrasts just make the wanderlust grow stronger.
So, when I miss my Tuscan time I doubt I will dwell on the photos I took, or these words I wrote. I think I’ll take a trip to the hills that brought me here in the first place to make more incomplete imaginations of the spaces I would like to be. Then, I won’t have to be stuck in the past as I look forward.
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