Travel Doesn’t Always Go to Plan. That’s Why I Make One.

Social media makes it incredibly easy to show you exactly the version of travel I want you to see. I can post the bowl of tortellini in brodo in Bologna, the glass of wine at aperitivo, the beautiful piazza and the carefully selected photo where the lighting is good and I’m looking particularly well-rested and European. What you don’t usually see are the puffy eyes, greasy

hair and general look of defeat that comes after more than 24 hours of traveling on almost no sleep.

And I get it. The beautiful parts are fun to share. They’re part of travel, too. But so are

delayed flights, missed sleep, wrong turns and those moments when you’re standing in a train station wondering how something you’ve done many times before suddenly went very wrong. So, in the interest of showing you a slightly less curated version of travel, let’s talk about how we actually got to Bologna.

We Planned Ahead. Travel Had Other Plans.

The chaos started before we even left home. Storms were expected along the East Coast, and our friend Stephanie, who is a flight attendant, suggested that my mom and I change our flight from Richmond to Washington Dulles to an earlier one. Our original connection before the overnight flight to Rome was tighter than she liked, and she knew that weather can create problems throughout the airline network even when the skies above your own house look perfectly fine.

It was very good advice. We changed our flight and suddenly had close to five hours at Dulles. Perfect. We could have lunch, go to the United Club, relax for a while and casually stroll to our gate like the seasoned international travelers we clearly are. Except our 10:30 a.m. flight from Richmond didn’t leave until almost 3 p.m.

Our carefully constructed five-hour cushion disappeared. By the time we finally arrived at Dulles, our leisurely layover had become getting off one airplane, making our way across the airport and essentially walking straight into boarding for the next one. We had successfully planned ahead for the delay; the delay simply used all of the time we’d planned ahead with. But here’s the important part: it worked. Had we kept our original flight, the story might have ended very differently. Instead, slightly frazzled but still on schedule, we boarded our flight to Rome.

Unfortunately, I barely slept. By the time we landed at Rome Fiumicino the next morning, my brain had been awake for entirely too long. This is where I should point out that I’ve done this before. I’ve flown into Fiumicino many times. I’ve taken the Leonardo Express from the airport to Roma Termini many times. This was not some complicated new transportation system I needed to figure out.

Apparently, my sleep-deprived brain disagreed.

My mom and I got on a train at the airport that was, technically, going toward Rome. It was not, however, the Leonardo Express. I realized this when the screen next to us said the nex stop as Parco Leonardo right after the doors closed, which is generally not something you want to see when you’re sitting on a train that’s supposed to run nonstop to Termini. For someone who plans travel professionally, I would like the record to show that I am also perfectly capable of getting on the wrong train.

Thankfully, we live in the age of smartphones. I pulled out my phone, figured out where our mystery train was actually going and found another route to Termini. We hadn’t created an international crisis; we had created a detour. So we adjusted, eventually made it to Termini and got on another train—this time the correct one—to Bologna.

The Point of Planning Isn’t Perfection

I plan a lot. Obviously, it’s part of what I do as a travel advisor, but it’s also how my brain works. I like knowing where I’m going, how I’m getting there and what happens next. I think part of me has always treated planning as a way to eliminate uncertainty. If I research enough, book the right things and think through every possibility, maybe everything will happen exactly as expected.

Travel has repeatedly informed me that this is adorable.

Flights get delayed. Weather happens. Trains go on strike. Restaurants close. Reservations get moved. And apparently sometimes the travel advisor gets on the wrong train. You cannot plan your way out of every possible problem, but you can make a good enough plan that when something changes, you have something to work from.

Changing our flight didn’t prevent the delay. It gave us enough time that the delay didn’t cost us our flight to Rome. Knowing where we ultimately needed to go didn’t prevent me from getting on the wrong train, but it meant that once I realized what I’d done, I could pull out my phone and figure out another way to get there. That, I think, is the difference. The goal of a travel plan isn’t to guarantee that nothing goes wrong. It’s to make it easier to adapt when something does.

By the time we reached our Airbnb, we’d been traveling for more than 24 hours. We’d done the literal planes, trains and automobiles. I’d barely slept, my eyes were puffy, and my hair had reached a level of greasiness that no amount of dry shampoo was going to negotiate with. I took what can only be described as an unnecessarily hot shower. After airports, airplanes, trains, train stations the full-body sanitization felt necessary.

As I started writing this, I was sitting on the balcony of our Airbnb in Bologna, freshly showered and finally feeling human again. We’d made it. It hadn’t gone exactly according to plan, and that was kind of the point.

The photos I bring home from Bologna will show beautiful porticoes, plates of pasta, glasses of wine and moments where I look considerably less like I’ve just crossed an ocean without sleeping. Those moments are real, but this was real, too. Travel can be beautiful and exhausting. It can be carefully planned and completely unpredictable. You can be an experienced traveler and still make mistakes.

A good trip isn’t one where nothing goes wrong, and being a good traveler isn’t about never making a mistake. Sometimes it’s just realizing you’re on the wrong train, pulling out your phone and figuring out another way to get where you’re going—preferably followed by a very hot shower.