Those “Oh-Shit” Travel Moments

Anyone who has traveled enough has an “oh shit” story. That time you drove hours to see a concert, then realized the tickets were back home on the kitchen counter. The night you got lost wandering around after dinner then suddenly found yourself in a sketchy part of town. The second you spotted the keys laying on the seat locked inside the rental car.

If you’ve had one of these moments, chances are you are still telling the story. Always accompanied by fits of laughter.

While these incidents are rarely fun while in progress, they become pivotal moments of the journey, requiring you to improvise, to figure things out, to find a different path.

I’ve had my fair share of ups and downs, near misses, and unlikely encounters on the road. Truly enough to write a book (hey, there’s an idea!)

With each episode, I’m reminded again to take deep breaths and trust the process. Getting upset doesn’t help, it only makes any situation worse. There’s almost always a way through.

Finding that way, and appreciating the unexpected outcomes, is what I love about traveling.

Here’s a two-punch “oh shit” story where my husband and I served as equal contributors in creating trip drama and now both share in laughter at its recounting.

Italy 2004

Every Italian we met during the two weeks we crisscrossed the roads of Tuscany who knew about our next destination, Isola del Giglio, said the same thing. “Do not take a car on the island.”

View of the lovely and lively port of Giglio

The very elements that make Giglio so magical – dramatic seaside cliffs, harrowing mountain inclines, narrow switchback roads – make it a driver’s worst nightmare.

With every intention to heed the warning, we arrived at Porto Santo Stefano to find no parking and a queue for cars boarding the ferry. Rather than miss a day in Giglio we made a split-second decision to jump in line. How bad could it be, right?

Giglio, a small island off the coast of Tuscany, has always reveled in sun-drenched tranquility and a certain remoteness (that is, until the Costa Concordia struck a rock just off the island in 2012.) The island is approximately 17 miles long and only a handful wide, it’s easy to explore the three settlements and numerous sandy beaches and coves via public bus, bike, and hiking.

We would leave the car parked during our entire visit. Solid plan.

Upon arrival, we found the small parking lot at Saracena Hotel filled. Being the helpful wife, I said, “There are probably spaces up there.” Matt dropped me with the bags and drove the direction I pointed. Up.

The lovely Saracena Hotel on GiglioThirty minutes later in a room with a view – of a ledge tumbling to vast ocean – and no sign of my husband, I began to worry. When the hour mark hit, panic creeped in. Should I stay in case he came back or go in search? Neither of us spoke Italian and this non-touristy island was unlikely to have many English speakers. If something had happened, how would I find him?

The 90-minute mark, I’d wait for it, then go in search. When it came, I was on the street, mind swirling with possible scenarios. None good.

Then I spotted the car. Matt was driving down the same road he disappeared up. Some guy was in the passenger seat. They were both soaking wet. My first thought was “He’s been swimming?!”

Nerves still rattled, Matt and his passenger began to spill the story.

Driving up for a few minutes, Matt realized this road was more like a path. With an intense pitch, getting narrower. He pulled into a steep drive to turn around when the car began to slide toward the cliff until it was mere feet away. Tires were losing traction and every maneuver brought him closer to the edge. He lifted the emergency brake and got out to consider options.

A few Italians walked by with suggestions Matt had already tried. Some just kept walking. Then, he spotted a couple coming up the hill. The guy was blond and wearing an Abercrombie & Fitch t-shirt. An American, surely. This guy could help.

“How’s it going?” Abercrombie said without slowing pace.

“I’ve been better,” Matt replied as he watched his only hope walk by.

Once the couple, Paul and his Italian wife Alessandra, reached their home on the hill, she said “I can’t believe you’re not going to help a fellow American.” Like most residents of Giglio, they were not happy to see tourists on the island. Especially stupid ones, who brought along cars. Still, as they unloaded groceries, Paul knew the guilt would be too much. He had to go back.

He and Matt agreed the best option was to lift the car and inch it away from the cliff. Half-an-inch by half-an-inch, they angled the car to safety.

In appreciation, we took Paul and Ale to dinner that evening. This turned into a nightly ritual of dinner, many bottles of wine, and the sharing of countless stories.

On the day we left, Paul met us at the ferry and said, “If you ever need anything, don’t hesitate to call me.”

My turn to be a “stupid-tourist.”

We were happy and relaxed. It had been an amazing time on Giglio. With the windows down, Italian pop music blaring, we made our way to Orvieto to drop the car and grab a train to Rome. We would fly home in two days.

As my mind floated through daydreams in the passenger seat, I began to think about travel and the desire to go everywhere. All those passport stamps to come.


With a chill-inducing lighting flash, it hit me. I didn’t have our passports. In fact, I hadn’t seen them in days. Then I remembered. The hotel had kept them at check-in.

I looked at Matt who seemed so serene and knew quick was the only way. “Honey, I think I left our passports on Giglio.”

Brakes slammed, the car came to a screeching halt and my husband looked at me with eyes I was sure meant “as soon as we get home, I’m filing for divorce.”

He turned the car around heading for the last village at a speed that would make pedal-loving Italians tremble. I assured him I knew what to do. “Just find a payphone.”

He answered after a few rings. “Hi Paul, it’s Jessica, your friend from Alabama. Remember me?”

Give him twenty minutes he said, then call back.

In what seemed like twenty hours, I wondered if Matt would ever calm down and if Paul had regretted his parting words to us at the ferry.

On the second call, I knew everything would be OK. Paul had the passports, he was planning to be in Rome two days later and would bring them to us in time for our flight. All stress went away, we knew he would come through for us. We began calling him our “travel fairy” and vowed to repay his kindness at every opportunity.

Visiting Spello with Paul and Ale, 2006

That’s the story of how we meet our dear friends Paul and Ale. Since that trip nine years ago, we’ve shared more adventures. Wherever we are, at some point, we always end up laughing until our bellies hurt over those two “oh shit” moments that brought us together and sealed our friendship.

We just finished another trip, exploring and hiking in Trentino. There were no incidents, no near misses, no need for the travel fairy (this time), just much laughter accompanied by copious amounts of vino. Travel perfection.

Family dinner with Paul and Ale – Merano, 2015
Light at the end of the forest tunnel. Vattaro to Caldonazza hike.
Paul, Ale, Matt, and Jess – Caldonazza 2015

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