In the summer of 2003, I was staying on the island of Capri with a group of students from the United States. Capri was an island every bit as gorgeous as I had been told, but my fellow students preferred to lounge around the pool at our villa drinking overpriced beer, which honestly you can do anywhere.

What I really wanted to do was to visit the Villa Tiberio, the hilltop home of the second Roman emperor, Tiberius, to which he had largely withdrawn for the last years of his rule. It had been, for all intents and purposes, the capital of the Empire, and it was there that Tiberius—Caesar during the Crucifixion—had died and his insane successor Caligula had seized his signet.

I wasn’t able to convince anyone to go with me to the Villa. The misty rain and my vague directions didn’t help, but the previous day had been sunny and everyone had opted for more lounging around the pool, more sipping beer, rather than what might have been their only chance to see some of the most important ruins in the world.

So I set off by myself, in the rain, with only a guidebook, my camera, and a rain poncho. The bus ride from our villa in Anacapri to the main settlement wasn’t for the faint of heart in the best weather, verging as it did on sheer seaside cliff above azure waters, and the slick roads made me edge toward the inner side of the tiny Italian bus ever more sharply. Deposited quayside in the village of Capri, I hiked the remainder of the way—perhaps a mile—in the rain.

In time, despite my efforts to get lost, the ruins emerged from the mist. They were red brick, capped with mortar of much later manufacture to keep their decay at a minimum, almost disappointing in how much the buildings of two thousand years ago resembled the buildings of today. Some archways still stood, and I sheltered in them from the rain with a slight tingle on my spine. Those same archways had been trod by Tiberius and Caligula, the former a tortured man who had nevertheless ensured his empire would last for 1500 years, the latter the sort of insane despot who would ensure it lasted no longer.

As I climbed the hill on which the villa was situated, I eventually made it above the rain clouds that had concentrated in the lowlands. Capri is vaguely saddle-shaped, and I emerged at the peak opposite the one where my group was staying, on a small hill. Like most small hills in Italy, and most Roman sites, it was topped by a small church, locked tight.

At that church, I met a fellow hiker—the only living human I saw all afternoon. I never did get his name, but he was an American, like me. He had worked as a software engineer back in the States, only to be let go after the worldwide economic downturn that followed the dot-com bubble burst and 9/11. They’d given him six months’ pay as severance, and he had decided to use it to see the world. he couldn’t be sure what the future would bring, but he wanted to be sure he had the experiences he could in the meantime.

I often think about our chat there, surrounded by two thousand years of history. I’ve had many opportunities to go abroad since, and I have tried to seize upon each of them regardless of the cost in time and treasure. Because as I look at my life as it has been since then—stultifying, sedentary, single—it is always instructive to remember the gentleman who set out in circumstances so unsettled I could barely conceive of them to experience what he could.

I’m not so foolish that I can claim that the encounter changed my life. I’m still cautious, conservative, a creature of habit, a confirmed homebody, single as Lonesome George. But there’s lesson and metaphor in the encounter nonetheless, I think. I disdained my fellow travelers for remaining poolside with their beers when there was a world to explore, yet the traveler I met showed me that more often than not I am seated by my own pool with my own beer, rejecting the fantastic in favor of the familiar.

And so the assorted travels since then—Vietnam, France, Qatar, and (if all goes well) Russia—have been my weak and sporadic attempts at going against my nature and living like the gentleman I met: like I had six months’ pay in my pocket and nothing to lose. If I leave this world unexpectedly, with my goals unmet, I will at least have had those few and paltry experiences, and the few soggy words I have thrown together.

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