In case you missed my first two installments of this piece, check out Florence Day 1 and Florence Day 2.

An alarm on vacation is an anachronism, a barbaric device from another time and place. It transplants itself from your working life into your life of leisure. In the milliseconds after my alarm went off, I instantly tumbled into dread and anxiety. Back in Los Angeles, alarms meant heading out into the big scary world and pretending to be an adult. That’s where my sleepy brain went. As my eyes slowly cracked open, I took in the room around me. Oh that’s right! I wasn’t in L.A. I was in Florence freaking Italy!

Maria and Alicia were already at the kitchen table noshing on a light breakfast and coffee when I walked in. Today was the big day. When Maria gets excited, she does this bounce-dance-hop thing. It’s her form of travel when she’s in a state of anticipation. Upon seeing me, she jumped out of her chair and bounce-dance-hopped over to hug me good morning. Ever since we were little, she’s had a perpetual “outside voice” that gets even louder when she’s excited. It was particularly oustidey as she screamed good morning directly into my eardrum. I looked over to Alicia who was also visibly excited, if not on the edge of bounce-dance-hopping over to me herself. 

As quickly as possible, I tried to get coffee into my body without burning my internal organs. With caffeine making its way into my system, I started buzzing along with Maria’s energy. If today matched 1/10^th of our expectations, then it was going to be an incredible day. We were going on a full-day bike tour of Tuscany, complete with a wine tasting, pasta lunch, and touring a real castle. 

We loaded all our metaphorical eggs into this basket. This was going to be our last day in Florence which meant our last day in Italy. It was the big finale, or so we hoped. The last moments of a once-in-a-lifetime trip. It was a risky move. As an all-day excursion, if it sucked, there was no escaping it. But if you want to win big, you have to risk big. As I got dressed, I ran a risk-reward analysis in my head. I concluded that a terrible tour in Italy with your best childhood friend and her mom was still better than your average day doing nothing in Los Angeles. I laced up my shoes feeling confident that that the tour itself could blow chunks and we’d still have an amazing experience.

Maria was most excited about getting outside. For being a lifelong city girl, she’s always had an affinity for the outdoors. When we were little, I wrote her a poem that included the line, “a nature girl who loves grass and trees.” We still laugh about that every now and again (sidenote: I’m an incredible poet). Aside from swimming in the Mediterranean, we hadn’t done much in the nature department while in Italy ( <- possibly the most braggadocious sentence ever written). This was her chance. 

Alicia was most excited about the biking, or “cycling” I should say. She’s an avid rider, hitting up long Saturday bike rides with her girlfriends. She may argue that “avid” is an overstatement, but, to me, anyone who rides more than twice a decade is considered “avid.”

I was most excited about visiting this castle-turned-winery. Though I know diddly about history, I love old things, especially old buildings. They are a standing relic of lives once lived. I always find myself pondering about the people who constructed the building. There was a person, someone lost to history probably, whose name may never be spoken again, who put that brick there and installed that window and hammered that nail. It blows my mind. The fact that this was a real castle that was now a real winery also blew my mind.

Nature. Bikes. Castle. Wine. Italy. 

On second thought, there was a good chance this was going to be a once-in-a-lifetime experience. 

Our American instincts to be early meant we waited outside the locked tour office until an employee strolled in. The sign above the door read: Tuscany Bike Tours, put some fun between your legs.

I had found my people. 

We signed some poorly translated liability waivers, then stepped outside again as the tiny office filled up with other tour guests. The others were mostly American and most were a couple. There were some newlyweds and a few college students. 

Two Italian guys, in their mid-to-late 20’s, came bounding down the narrow cobblestone street and into the office. The Italian spoken between them was liquid and fast. They were wiry, tall, dark, effortlessly high-energy but cool, and attractive in the way that passionate men are always attractive. Upon seeing the small crowd outside the office, they seamlessly switch to English as though they had been speaking it the whole time and began to greet everyone like we were distant cousins arriving for Sunday night dinner. Our guides had arrived. 

Before realizing it, we were loaded into two passenger vans and driving into the heart of Tuscany, leaving Florence in our wake. Our guide, whose name I regretfully cannot remember but for the sake of this story I’ll call Tony, talked the entire way. He wasn’t an obnoxious talker, in fact, he was quite the opposite. His deliciously-accented English was candy for my ears. He engaged everyone in the van, asking us questions about where we’re from and what we do. His laugh was generous and immediately made everyone comfortable, even familial. This was much appreciated because, had I not been distracted by Tony’s personality, I would have had an aneurism over his driving. It’s possible that during our 40-minute drive, he looked at the road a total of 3 times. Everyone was falling just a tiny bit in love with Tony, so this was a forgivable offense even if technically life threatening. 

The terrain of Tuscany is gentle. One moment, we were in a bustling city and the next we were surrounded by green rolling hills, unaware of how exactly that transition happened. It feels like a cliché to say “rolling hills” but there’s really no other accurate description. The lush green-brown vineyards look as though they’re merely a blanket floating on top of calm oceanic waves. Everything about the landscape caused my system to relax as I looked out the window. The rhythm of Tony’s voice, the metronomic spin of the tires below, and the hills all around seemed to be falling into sync with each other and sent me into a hypnotic trance. It was one more instance of Italy creeping its way into me and captivating my heart, as if it hadn’t been doing that for the last 9 days. 

Tony was in the middle of some enchanting story when he lowered his voice.  The van slowed down and turned onto a dusty road. Lofty cypress trees enveloped our vehicle on either side. It was hard to see from where I sat but I caught a glimpse of a castle, the castle, sitting at the end of the road. The whole van hushed as though the sight were something sacred. 

Once Tony put the van in park, I couldn’t get out fast enough. The castle was calling me, and I felt as though I had cocooned in that van for a lifetime. One by one, we spilled out onto a gravely driveway as though emerging from the wardrobe into Narnia itself. My heart went pitter-patter as I looked straight up at a mammoth, sand-blonde, Italian castle. We were here. 

The castle was quite square and angular. It looked like one giant rectangle with high walls and a square tower jutting up into the sky. I peered down a long tunnel whose iron gate at the end separated the world from the castle’s inner sanctum, a courtyard. In most regards, the castle was a simple stone building with little architectural ornamentation here and there. Its size and its being an actual freaking castle kept me mesmerized though. My neck was craning as I looked up toward the tower. A young woman with dark glasses and black hair loosely pulled back in a bun approached our group. She and Tony greeted as though they were dear lifelong friends. I would eventually come to believe that everyone thinks of themselves as one of Tony’s dear lifelong friends, even brand spanking new acquaintances (like myself). 

The woman worked for the estate, Tony informed us. She would show us around, then we’d have a wine tasting before heading out on our bikes. Like one big organism, our tour group followed behind her through the long tunnel. My fingers lingered on the iron gate as I crossed the castle’s threshold. The courtyard was as Italian as anything, with potted succulents and an ancient stone fountain. Standing in the middle of that courtyard, I still couldn’t believe I was there.

The Castello di Poppiano was built sometime around 1000 A.D. Oddly enough, it wasn’t originally intended as a tourist destination for Americans. Its proximity to Florence meant it could provide some defense should any armies invade from the southwest. The Guicciardini family took ownership of the castle some 9 centuries ago, a fact that nearly made my eyes pop out of my head. For almost 900 years, one family has owned and operated the castle. 

At one point, the Guicciardini’s capitalized on the grape and olive growing abilities of the region. They established wine and oil making practices that they still employ today, with much of the work being done inside the castle itself. Every couple of decades they’ll update a piece of equipment, but, other than that, they stay true to their roots. Conte Ferdinando Guicciardini still oversees all wine and olive oil production. As our guide talked, I tried to hold on to as much information as possible, but my senses were being overtaken by the castle. Maria had wonderment all over her face. 

We travelled from room to room looking at how the vineyard made wine and oil. This was the room where they pressed the grapes. This was the room where they pressed the olives. We entered a dark and expansive room that contained row after row of colossal wooden barrels where the wine was aged. The wine enthusiasts of our group identified themselves whenever our guide asked a question. They were practically salivating on the floor as she discussed the specific type of wood and age of the barrels used. I felt dwarfed by the enthusiasts’ knowledge and the barrels themselves. 

Tony told us to get our cameras ready because we were about to go to the top of the tower. What made the castello so visually imposing, to incoming armies and tourists alike, was its single square tower, or “donjon” if you speak Old French. It professed itself proudly, the tallest thing for miles. Tony, who had probably been to the castello a hundred times, was giddy as he told us this. 

We ascended the stairs. This was certainly not for the faint of heart or those who suffer from claustrophobia. The wooden steps seemed too old and too worn to actually bear the weight of a human. Maria followed behind me and I thought that if I fell through the steps, maybe she would have enough time to catch me, or at least grab a fistful of my hair. My hand grasped at the stone wall for balance, avoiding spiderwebs as best I could. Much like crawling out of the van and spilling into Narnia, we emerged from the stairwell onto the roof of the tower. 

Damnit Italy! How do you manage to make every view, every moment, every space so extraordinary, so spectacular?! The top of the tower offered a 360-degree view of Tuscany. What I saw from the passenger van below now seemed like a dirty postcard compared to the vision laid out before me. Those rolling hills were now even rollier. Their green dreaminess seemed to stretch out into infinity. Somehow the air felt cleaner, too. The sun was bright, but not too bright. I felt certain that if I looked hard enough, I would find a seam somewhere in the landscape. Surely this scene of perfection had been painted by someone, like flats used in old movie musicals. Every cloud, every vine, every hill seemed to be placed and shaped with nothing other than total intentionality.

Our group took a crazy number of pictures, as though, somehow, we could capture that living moment of transcendence on film (and by film, I mean iPhone). The pictures were a moot point though, because I was never going to leave that tower. My eyes would never forgive me if I deprived them of that view even for a second. Then Tony said it was time for wine and my eyes magically conceded to heading back down the stairs. 

Back in the courtyard, we sampled all the wines produced at the castello. We learned about tannins and I did my best not to eat all the breadsticks that were set out. Once everyone was sufficiently tipsy and had purchased all the bottles their hearts desired, Tony announced that it was time to leave. It was barely noon. 

He and his partner took us around the castello to a little shed. That’s where Tuscany Bike Tours stored all the necessary bikes, helmets, and equipment. I hadn’t questioned the fact that, 3 hours into this bike tour, we had yet to see an actual bicycle. Maria started to bounce-dance-hop again as we were outfitted with helmets. Had it not been for the slight buzz the vin santo had given me, my nerves would have kicked in at that point. It had been years since I rode a bike. Surely, I would be able to do it. The question was whether I could do it without embarrassing myself in front of Tony, who was now my best friend, and these strangers. 

Before we headed down the dusty road we came in on, Tony and the other guide informed us that, should anybody get tired of riding, one of them would follow with the van. We could wave them down and put our bikes in the back. The vin santo must have inflated my confidence because I scoffed at such a suggestion. The whole point of this tour, aside from getting tipsy on castle wine, was to ride a bike through Tuscany. Haven’t people made entire movies about this? Why would I admit defeat and get in an air-conditioned passenger van? Clearly I was tipsy. 

Once we got rolling, the riding was as casual, easy-paced, and delicious as the whole of Italy had been. We took roads, some paved and some less paved, that meandered through the countryside. I’ll admit that sometimes, those soft, rolling hills I saw from the donjon were a little harder and little less rolly when I had to get my ass over them using only leg power. Nevertheless, the quiet sounds of nature filled my ears as we passed row after row of grapevines. Save for the occasional car that passed us, all of Tuscany was ours.

During the ride, different groups and pairings would form and disperse. Sometimes we could ride side-by-side, sometimes we needed to be single-file. Mostly I was in my own little zone. At one point Tony was next to me. My heart perked up and I did my best to impress him with my ability to not fall off a bike. He told me a little more about the area. The town of Poppiano is quite small, I found out, with a population of less than 1,000 residents. Most of the people in the area are connected to the castle and its winemaking in some way. The town is in the commune of Montespertoli, a name that my tongue trips over but still loves to say. He warned me that we were coming up to pretty massive hill. If I wanted to hop in the van, I should do it after our next rest stop. Again, I scoffed. Didn’t this Italian fool know I did CrossFit?! Maybe my buzz hadn’t worn off yet. 

While at the rest stop, Tony informed our whole group just how steep that upcoming hill was going to be. Anyone who wanted to ride in the van should get in now. Most of the group saw this as the more reasonable thing to do, including Alicia and Maria. Everyone was hot and sweaty, having been riding for the last two hours. 

Tony and the other guide warned those of us who remained one last time just how steep it was. He said that the road was too narrow for the van to come back down once it got to the top, so we couldn’t quit in the middle. Our decision to ride would be final. No exchanges or refunds. We, the strong ones, the stubborn ones, the male ones, collectively scoffed. The chianti still had a stronghold on my judgment. 

Fast forward 20 minutes and I’m huffing my ass up a mountain at what felt like a 45-degree incline. I was pissed but only had myself, and maybe the wine, to blame. At one point, I completely abandoned the notion of riding my bike and simply walked next to it. It was so steep that even walking felt like an achievement. The van had given us (idiot) riders a head start, while the others loaded their bikes into the back. I was close to tears when I heard the van creep up behind me. My pride was at stake. I instinctually got back on my bike. In the hopes that I would stave off actually rolling backward down the mountain, I pedaled as hard as I possibly could. As the van rode by, I pretended to be someone who wasn’t going into cardiac arrest. Maria and Alicia waved from inside the air-conditioning. I’ve never hated them so much. 

By the time I got to the top of the “hill” (again not an appropriate use of that word), everyone from the van was casually relaxing at a charming watering hole. I, and the bros dumb enough to try and bike the mountain, rolled up looking like we survived war. Maria handed me her water bottle and tried not to laugh too loud. I considered my lesson learned.

We were told that the rest of the ride would be mostly downhill, not surprisingly. 30 minutes later Tony peels off down a small dirt road and we follow. It was time for lunch. I sent up small prayers of thanksgiving as the wine tasting, sweating, and most-difficult-physical-exertion-of-my-life had left me famished. 

The restaurant was a small nondescript building that appeared to rise up from nowhere, surrounded only by vineyards and cypress trees. We parked our bikes and filed in like obedient tourists. As we walked in, Tony hugged and kissed the waitress and the owners as though they had decades of history between them. Their melty Italian spilling forth from their mouths. The owners had specifically opened their doors for us. 

My body rejoiced as I sat down on something other than a bicycle seat. The meal they served was simple and consisted of graphic amounts of pasta and bread. As I chowed down on my third serving, I thought, I would never and could never tire of the way Italians do carbs. Again, these were my people. Huge jugs of wine lined the table. Pasta and wine at every meal? Clearly, I was born in the wrong country. 

Everyone looked drowsy but content as we donned our helmets again. It was late afternoon and a melancholy washed over me as I thought of our short ride back to the castello. The day was coming to a close and then it hit me, that lunch was probably my last meal out in Italy. The thought was nearly overwhelming. Tonight would surely be an easy dinner at the apartment, using up the last of our groceries. Fortunately, a belly full of Italian table wine and the Tuscan landscape whirling pass my bike softened this sadness.

The ride back to the castello was decidedly tipsier than the ride away from it. It could have been the carbs, the wine, or my physical exhaustion, but I drifted back into a drowsy, blissful haze. I was wholly present and supremely happy. As I looked around I realized the magic of Florence, and all of Italy, had worked its charm on me. Like some kind of human dough, this entire country had kneaded me over the last 9 days. I had been subtly changed in ways that would take years to unearth and articulate. 

As we walked back to the apartment from the tour office, under a dusky pink sky, the thought settled over me that I would be on a plane to Los Angeles by the time the sun rose again. Were I to meditate on that too long, I would cry. Los Angeles meant feeling unconnected, unsafe, and untethered. The last 9 days were all about connection, connection to strangers and new foods, connection to lifelong friends and laughter, connection to the excitement of newness. Perhaps with a little bit of effort, I could carry my new Italian sensibility, the one that this beautiful country and its people had been quietly kneading into my marrow, with me back to L.A. I would always have the pictures, the videos, and the trinkets. But most importantly, I’d have the feelings, the tastes, the smells, the sounds, the sensations. I would always have the memories. We paused on a bridge to look at one final stunning Italian sunset stretching over the Arno river. After a few moments of peaceful silence, Alicia, sensing our shared sense of bittersweet finality, turned to me and Maria and asked, “One last gelato?”

Huge thanks to Charming Italy, Visit Italy, and Conte Guicciardini for filling in some of my missing history.

All personal pictures provided by Alicia and Maria.