The Benefits of “Winging It” While Traveling

When a couple embarks on a spontaneous road trip through Italy, they rediscover the joys of unplanned adventure.

The Benefits of “Winging It” While Traveling

Sometimes the best way to hit the road is with no plans whatsoever.

Photo by Todd Klassy/Shutterstock

I deeply believe in not planning trips. Mostly because I’m lazy. But also because I think there is a lot of joy in discovery. When you’re measuring every meal, hotel, and medieval church against a guidebook description or friend’s recommendation, you’re not a traveler—you’re a critic.

My wife, Cassandra, however, is a planner. She is not the kind of person you tell to pack a bag because in an hour we’re going on a surprise trip. She’s not the kind of person you tell to pack a purse because we’re going to a surprise dinner. She doesn’t have OCD, but she likes things a certain way, and she’s a little compulsive about that way, and kind of obsessive, too, in a disorderly way.

So when, after we had dated two years, I gave Cassandra what she always wanted—a trip to Italy—I suspected she’d be so excited she would be willing to relax from the cruise-director-level itinerary planning she did for our previous trips.

My favorite movie is Eternal Sunshine of the Spotless Mind, partly because I walked into a screening without knowing anything about it other than the title and who wrote it, and partly because it’s a movie about the joy of having your memory erased so you can fall in love with the same person again. If Cassandra and I could have those kinds of surprises together when we traveled, it would be far better than just doing what the Fodor’s guide recommended. I wouldn’t have even bought a Fodor’s guide for her if Hallmark had a card that said, “Happy birthday! I’m taking you to Italy! Let’s have sex tonight!”

We’d drive to a town we’d never heard of and spend the afternoon walking around, choosing a hotel and then a restaurant at random.

The encyclopedia-size Fodor’s guide actually overwhelmed Cassandra so much that she was willing to compromise on a bare-bones plan: We’d fly into Rome, drive to Florence, and then drive back, making spontaneous stops along the way. “Structured winging it,” she’d later say.

And we really did wing it. Even though neither of us had ever ridden a scooter, we rented Vespas in Rome—something I’m pretty sure we would not have done if we had read that there was a 90 percent chance of getting killed at every traffic light. We knew blessedly little. When we left Rome in our rental car, we were shocked by the orderliness of the autostrade, where the left lane really is for passing. We were even thrilled by the Autogrills, which are to American rest-stop fast-food joints what all Italian restaurants are to all American restaurants. We had no idea that people spoke a wonderful, strange language called “Italian.” I still call Cassandra, at our best times, “Principessa.” And because we did so little reading, I still have no idea what it means.

We’d drive to a town we’d never heard of and spend the afternoon walking around, choosing a hotel and then a restaurant at random. It’s a great way to see a place, compared with staring at a guidebook, ignoring everything on your way to the old church. My dad loves cruises because he can get guided tours of historical sites and not waste a lot of time moving his luggage from hotel to hotel and thinking about what restaurant to eat at that night. I, on the other hand, hate history, since you cannot eat it.

Orvieto is a small city perched on a volcanic stone cliff in Umbria, Italy.

Orvieto is a small city perched on a volcanic stone cliff in Umbria, Italy.

Photo by canadastock/Shutterstock

Sure, our lack of knowledge caused some difficulty, like when the annoyed waiter had to use broken English to tell us we couldn’t order red wine for lunch in Orvieto, since what you drink in Orvieto is the local white wine called “Orvieto.” That’s difficult to explain even in perfect English. Or when we discovered that every town seems to take one completely random day off and close down, which meant that, a few times, we had no choice but to drive to the next town. “When the sun started to set, I’d get a little anxious,” Cassandra later admitted to me. But then she started to see things my way.

We didn’t fight, because there were no bad decisions: We were going to have great pasta, walk down streets filled with beautiful architecture, stay in an old hotel. Because we just had to head vaguely toward Florence, there was really no chance we were going to get so incredibly lost that something horrible might happen, like spending a night in Switzerland.

We didn’t fight, because there were no bad decisions.

Not having a schedule also meant that when the inevitable strike hit Italy and we couldn’t buy gas, we could just stay longer in our cottage in the middle of the vineyards of Radda in Chianti, where they turned off the electricity at 8 p.m. This turned out to be our favorite part of the trip. It also meant that if Siena seemed a little touristy, we could get some gelato, admire the Palio, and get the hell back in the car.

The only place we didn’t love was Florence. It was the one place we knew for sure had art, romance, and great food. And it did, but not as great as the art, romance, and food we’d heard Florence had. In the hill town of San Gimignano, however, the medieval towers, churches, and museum had no trouble exceeding those of the San Gimignano we’d never, ever heard of.

At a certain point on any trip, you have to give up control. Your language skills will fail you, and you’ll have to take whatever the waiter wants to bring over. And that bowl of tripe—and, no matter where you are, it’s always tripe—is what you love and remember. Cassandra and I took a trip where we metaphorically had tripe at every meal. Which, actually, nonmetaphorically, we nearly did as well.

>> Plan Your Trip with AFAR’s Guide to Italy

Joel Stein is an American journalist who wrote for the Los Angeles Times. He wrote a column and occasional articles for Time for 19 years until 2017.
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