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The Best-Laid Plans

No matter how many maps you consult or guidebooks you study, you'll occasionally go astray when traveling. Good thing, too, according to John Sellers, who boarded the wrong train in Italy and found himself by getting lost.

Photography Shonagh Rae

IT WAS ALMOST 10PM when I took a seat in the nearly empty train car in a desolate port city near Rome, bound for the capital. As the train began creeping out of the station, I could barely keep my eyes open, a side effect of the whirlwind nature of my trip. Or more precisely, the perfectly flawlessly executed whirlwind nature of my trip.

Only two weeks prior, I’d decided to treat my then- girlfriend, Kerry, to a brief getaway to Naples. The challenge? She was in the middle of a three-month cruise around the world and virtually unreachable by phone or email — except in emergency situations, like if she needed an update on her cat. So planning fell entirely to me.

Happily, I love to plan. I’m meticulous — painstaking even. I hunkered down in my Brooklyn apartment as if plotting a bank heist. Travel books were thumbed through, timetables consulted, maps pored over. After a few days, I devised the perfect plan. Knowing that Kerry’s ship would be docking for a few days in Civitavecchia, 50 miles northwest of Rome, I concluded that it would be best to meet her at customs. From there, first-class train tickets would whisk us south to Naples and the five-star hotel and the many Fodor’s-recommended restaurants I’d be ponying up for. All she had to do was show up.

And she did. And the whole thing went off without a hitch. Kerry had a lovely time, if I do say so myself. I’d just come from seeing her safely back to her boat and had managed to board the train back to Rome with 10 minutes to spare. Mission accomplished, or just about.

I just had to return to Rome to collect the suitcase I’d stowed at the rail terminal, check into the hotel I’d prepaid for and wake up early the next morning for a quick viewing of the Colosseum before taking a taxi to the airport for my flight back to New York. Despite having visited Italy twice before, I’d never spent any time in the Eternal City, and I was grateful to have even a few hours to see the sights. Doing so would require energy, but I’d planned for that, too. As the train lurched out of the station in Civitavecchia and began its 90-minute crawl, I closed my eyes and began to doze off, right on schedule.

I awoke roughly 40 minutes later. Glancing out the window, I expected to see the sprawl and twinkling lights of the Roman suburbs I’d noticed on the way out. Instead, three thoughts came to mind in rapid succession: (1) We’re really moving! (2) It’s crazy dark outside. (3) Uh-oh.

Time to hunt down the conductor. A bearded, officious man in a blue hat flashed me a puzzled smile as I stumbled up the aisle, trying — without success — to appear calm. I scraped together a sad remnant of what little Italian I remembered from college. I’d briefly studied the language in the hopes of using it to seduce an Isabella Rossellini type or order a pasta dish more authentic than Chef Boyardee, not to engage in panicked conversation with transit workers.

“Dove andiamo?” I asked.

The conductor replied, in broken English, that our train was headed north, to Livorno, two hours farther on. I felt my whole body slouch in defeat. Livorno! He made one of those politely bureaucratic shrugs that universally indicate “You’re screwed” and beckoned me into his office compartment, where he sat down and began flipping through a massive tome containing what I assumed to be every train timetable on the planet. After a short time he looked up at me.

“Is no good,” said the conductor. “What’s no good?” I asked.

“You.” He punched his index finger at the timetable. “You is no good.”

He went on to explain haltingly that while, sure, I had blundered by boarding the wrong train, the actual problem was much more severe. At virtually any other time of day, I could have disembarked at the next station, waited a short time, and then caught a train heading back to Rome — a mere inconvenience. But there were no more Rome-bound trains at this time of night; service wouldn’t resume until the next morning.

Translation: I would not be spending the night in Rome.

The smugness I’d been reveling in just an hour before had given way to extreme anxiety — and a dawning realization that perhaps the reason I’m such a careful planner is a simple fear of losing control. Improv isn’t my strong suit. The conductor instructed me to get off at the next stop, a place called Orbetello, where the first train tomorrow would be departing around 5:30am, reaching my intended destination some two hours later.

Once this information had sunk in, it didn’t seem so bad, actually. Sure, I’d be squandering the $150 I’d fronted for a room in Rome, but I’d still have sufficient time to hit the Colosseum before setting off for the airport.

And it was still early enough now to get a decent night’s sleep at a hotel in Orbetello. I could feel myself starting to replan. It would all be fine. I shook the conductor’s hand and hurried back to my seat to grab my backpack.

A few minutes later, around 11, I stepped off the train in Orbetello, a small, coastal Tuscan town. No one exited with me. Nice, I thought, I’ll have first dibs on the taxi line. But as I strode down the platform toward the exit, I noticed something odd about the small train depot. It had no employees. Nor waiting passengers. I was entirely alone.

I hotfooted it toward the exit, anxious to hail a cab and put my blunder behind me. A blast of cold air smacked me in the face as I opened the door, which slammed shut with a theatrically loud clang. Its echo heightened the sense of isolation I felt when I realized that there were no cabs waiting outside. I spied a café and a general store across the street, both shut for the night. Nothing stirred.

I sat back down in the empty waiting area — the lights buzzing torturously above — trying to think. Instinctively, I reached in my jacket pocket for my day planner, then scanned the pages of information — all of it useless.

Near the station’s shuttered ticket window, I found a map, which informed me that while this was indeed the train station servicing Orbetello, the town proper and its population of roughly 15,000 souls lay some three miles to the west. Aha, I thought, civilization. My spirits rose further when I found an information guide on the wall above a pay phone listing the numbers of two local taxi operators. Pay dirt! This wasn’t so bad after all. I even had a few lire. I dialed the numbers triumphantly… and neither service answered.

Fine. I quickly plotted a walking route into Orbetello. Three miles would take me roughly one hour. Surely there’d be a place to stay in town or, at the very least, a late-night café or bar to sit in while I passed the time.

And so, I resolved to walk. Now, I am well aware of the safety maxims stating that you should never leave the car if you get caught in a blizzard or lose sight of the trail if you’re in the woods. But I’ve never read any primers on what not to do if you get stranded in Middle of Nowhere, Italy. Given the relative misfortunes I’d already suffered that night, you’d think that I would have had the good sense to stay put. And it was true that no one knew where I was — not even Kerry. It might take days for someone to notice that I’d gone missing.

I’m man enough to admit to being freaked out as I set out from the station along a country lane illuminated only by moonlight. I had to check frequently behind me to see if anyone — deranged butcher, headless horseman — was following. About 10 minutes in, my footsteps the only sounds other than the whipping December wind, I passed a seemingly deserted two-story villa standing alone in a field. It struck me as both hauntingly beautiful and hauntingly haunting. I imagined I’d stumbled into one of those tourist- in-danger exploitation flicks and would soon be forced to make a terrible choice between sawing off my own foot or staying chained in a room and forced to watch Roberto Benigni movies on an endless loop. I quickened my pace.

A little while later, the road rose up an embankment to join a larger thoroughfare, the fancy kind with street lamps and everything. A car whizzed by. Soon I reached a residential neighborhood of cozy, dwelled-in rowhouses. And then I saw it: Orbetello! Like the Scarecrow finally entering Oz (if I only had a brain), I let out a whoop as I walked through the majestic stone entry gate that I would later discover is part of an ancient wall that rings the city.

Now for the easy part…

Well, not really. Not at half past 12 on a frigid Sunday night. But as I wearily trudged down narrow, silent streets hoping to chance upon someone who could point me toward a hotel, I realized that it didn’t much matter what happened at this point. Merely being in such an unlikely town at such an unlikely time was reward enough for my troubles. Isn’t the chance to get out of our comfort zones the whole reason we travel in the first place? Interestingly, while the details of even my most idyllic travel experiences — including my three days with Kerry — have blurred somewhat, my recollections of this ordeal remain ineffably vivid. So vivid, in fact, that I’ve come to regard the whole misadventure as the happiest of accidents. Indeed, ever since, whenever I’ve planned a trip, I’ve planned it just a little less thoroughly — leaving a few details unresolved, a few areas unmapped.

At nearly one in the morning, I found a café, open for another hour, where I drank two cups of the best coffee I’ve ever had. A friendly English-speaking barista let me in on a dark secret about Orbetello that I wished the train conductor had mentioned: Business booms only in the summer months, when vacationers descend on the place to sun themselves at the adjacent Tyrrhenian Sea. She gave me a number of a nearby hotel that was sure to have a vacancy and I thanked her for her help.

But instead of calling, I went outside and sat on a bench near the gate. After spending a half hour admiring the city wall — constructed, as it happens, more than 500 years before the Colosseum — I decided that my adventure would end here. As the sun peeked over the horizon, I strolled back to the station, where just before six, I boarded a train bound, finally, for home.

John Sellers is the author of The Old Man and the Swamp, a memoir to be published next year by Simon & Schuster.

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