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Travel & Adventure Living The Dream During a Snakebit Trip to TuscanyA wild experience under the Tuscan sun, featuring fine wines, ritzy villas, a bout of COVID, and poolside potbellies.

I’d come to Tuscany to write about a villa for Travel + Leisure, and a chamber music festival occurring on the villa’s grounds. I had no travel budget and wasn’t getting paid squat for the article, but on paper, it sounded like a holiday.

Fly over to Italy, indulge in wine, pizza, and pasta, and visit a historic villa. What’s not to like? It’d be like a dream.

Anyway, I’d pitched the assignment so that the trip could be a relaxing, luxurious vacation for myself and my girlfriend. When she bailed at the last minute, however, I found myself flying to Italy alone.

Things began to go wrong almost immediately.

I came down with a brutal case of COVID on my first night in Rome and spent five days sweating like a dog (this was July 2022, and the European summer heatwaves were in full swing) in a tiny rented bedroom with no A/C, fan, or window… I passed the time guzzling sparkling water and watching anime, while hordes of hungry mosquitos came from god knows where (see above: no window?) and feasted on my feverish blood.

I emerged from this hellish den emaciated and horribly behind on work, but had little time to recuperate before the festival. I rented a Moto Guzzi V7 two days later and fired up north to Tuscany.

The bike was a bit of a clunker, one of those rentals that have seen a few too many hard knocks and not enough TLC, but it got the job done. The heat emanating off the highway was abominable, it felt more like summer in Las Vegas than Italy. I drove past a sprawling wildfire in the hills north of Rome, the clouds of smoke only adding to my post-COVID cough.

In Tuscany several hours later, I pitched a tent in a cheap campground and drove 25 minutes to the villa in time for the festival. Upon arriving, I realized I’d simply pulled into some random guy’s driveway. I’d plugged the wrong spot into my GPS, and was over an hour and a half from the actual villa. I turned around and fired back in the opposite direction.

At one point, after pulling onto a highway and accelerating, my goggles flew off my helmet, landing somewhere in the road behind me.

Night had fallen, and I was running on fumes, both in the Guzzi’s tank and in my mind. I was going to be at least an hour late for the concert. Immediately, I rode into a ferocious thunderstorm. It was nearly pitch black, the headlights on the Guzzi were less than adequate, and lighting was blasting the hills all around like artillery fire. I tried to wait out the storm under the shelter of an abandoned gas station, but the rain only intensified, and then my phone died, so I had no way to navigate. Fueled by frustration, I blindly rode the bike a few klicks further up the road and was nearly washed into a ditch by a large van blasting past in the opposite direction through a foot of standing water.

Finally, I surrendered, pulling into what appeared to be a small pizzeria.

Moments later, dripping wet like the Swamp Thing, I inspected the lone slice of cold pizza sitting behind the clear plastic counter. It was topped with rancid-looking mushrooms and circular lumps of sausage that evoked images of testicles.

“You got anything else?” I asked the old man behind the counter.

He tugged on his saggy earlobes and shook his head. “We closing in eight o’clock,” he muttered, gesturing to the plastic clock hanging on the wall next to the TV, which was blaring 50s oldies.

I took the mushroom-testicle pizza, and in five minutes was back on the Guzzi. My phone was dead, and I had no real clue how to navigate the 50-odd kilometers back to my campsite, other than a general belief that it lay north-northeast.

It took me three hours to make the one-hour ride home, randomly taking roads based on the heading from my wrist compass and asking the few people out on the streets.

At one point, after pulling onto a highway and accelerating, my goggles flew off my helmet, landing somewhere in the road behind me. I pulled the bike over and spent fifteen minutes scouring the road for them, nearly being smeared by half-a-dozen cars in the process. When I finally found the goggles, they’d already been run over several times, and the visor was completely smashed out.

I arrived back at my campsite at half past midnight to find that someone had walked into my tent’s guylines, and the tent was completely trashed. Two of the stakes were bent beyond repair, and one was missing, so the lean-to tent was hanging over so low that the ceiling was smothering my face. To add insult to injury, my inflatable sleeping pad had also popped for some reason (maybe the guy had just full-on driven a truck over my tent in the dark, I dunno).

I was too tired to care, though, so I just said ‘fuck it’ and lay down on a towel in my underwear. I stared at the stars in the 85-degree nighttime heat, sweat beading on my bare skin, and thought regretfully of the $2,000 I’d already spent on this “vacation.”

The following night was the last night of the seven-night event, so I had to make it to the concert. Everything was riding on it. Otherwise, this whole hair-brained trip would be for naught.

I rolled up to the villa several hours early just to play it safe, parked the bike, and was informed that (perhaps rather obviously) none of my contacts would arrive for at least two hours, if not more. No one seemed to really know who I was, so I began wandering the property, taking photos where I could. The villa was sprawling, with expansive gardens, ornate architecture, and warm, yellow hills rolling all around. I got to see very little of it though, because within minutes I was accosted by an older, shirtless man sitting by the swimming pool, with a saggy pot belly that looked like it was filled with cottage cheese.

“This area, sir, this area is PRI—VUHT,” he declared, enunciating in a Trumpish manner with clasped hands held close to his chest. “PRI-VUHT. You cannot be here. It is a safety concern.”

When I told him I wasn’t trespassing, I was a journalist who had been invited to view the villa, he became rather obsequious, in. “Ahhh, well if you’re an important American journalist then… Well, of course…” He trailed off, flashing a moronic grin.

I left the villa and spent the remainder of the time drinking beer in a nearby restaurant that had more rules than a Catholic prep school. (“You cannot park the motorbike here in the gravel, you must park across the road. You may only order food after 4:00 pm. You must not drink directly from the beer bottle. You must use a coaster for this glass.”)

“Ahem, and which villa are you lodging in?” queried an older woman sitting at the table next to me, who looked like she’d been plucked straight from Downton Abbey.

“I have a campsite nearby,” I said.

She eyed me suspiciously, offering an “Ah” in response.

I looked down at my phone and saw an Instagram DM, in response to a photo I’d posted earlier. It was a picture of the Moto Guzzi with the rolling Tuscan hillsides in the background. A nice photo, I thought. A buddy from high school had responded to it.

Seems like you’re living the dream, dude, he wrote. I’m jealous!

Initially, I just laughed to myself. I had never felt more the opposite. Social media is funny like that. You’re just getting a snapshot of one moment in time, and even then only from a single angle. This guy was just seeing a nice bike in a beautiful country, not the dozen other frustrating situations hemmed in on either side of the photo. It made sense that he’d figure all was rosy.

But then I stopped, thought about it for a second, and responded honestly. Yeah, man. I guess I probably am.

Surprisingly, the music at the concert that night wasn’t half bad. I had a good time. I had excellent material for my article. All was well.

When I got back to my meager campsite and half-destroyed tent, I prepared for another sweltering Tuscan summer night. Before lying down, however, I chugged a bottle of wine.

It helped. At least until the morning.

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