The splendor of an itinerary-free trip

While we were corralled onto our flight home from Italy last month, I heard a woman use the sort of faux-perky tone that insists, “I’m happy about this, I swear!”

“It was a lot of fortresses!” she said, adding that they also “got a lot of steps in.” Her companions offered a smidge more honestly: “Yeah, you see one fortress, you kind of see them all.”

We did not tour any fortresses on our two-week trip. We didn’t do any tours at all. Other than catching trains, dropping off the rental car, or checking out of hotels, we didn’t have to be anywhere, at any time.

I am tethered to meetings and deadlines in my daily life. There is not a crumb of my soul that wants to live this way on vacation. To wake up early so I can hoof it to the museum at my reserved time, stand in line to see a famous work of art, and then mostly view it from the perspective of a stranger’s iPhone? Bury me alive in the basement of a AAA travel agency first.

Without yucking someone else’s yum, I’m going to plant my flag here: The best vacations are spent unscheduled.

Plenty has been written about how overscheduled our lives have become. What I struggle to understand is why we’d want this to creep into our time off as well. Why should our calendar reminders follow us overseas? Maybe because we can’t release the urge to accomplish or prove something.

I imagine this desire stems from two sources. First, our little brains have been poisoned to believe that nearly all of our experiences require an event debrief with key takeaways, in the same vein as a post-conference summary report. We should be able to rattle off highlights (favorite meals, best hotel, etc.) and provide accompanying visuals (here I am in front of a cathedral!) as though we are proving we did vacation right and our PTO is validated.

Second, we culturally don’t believe we’ve Done Anything unless we’ve had the opportunity to check it off of a list. Sixteen Must-See Vistas In Portugal. Five Under-the-Radar Spots for Gelato. The Secret Spot for Explosive Diarrhea That Locals Love. AND THEN there are the suggestions that you never Googled: As in, the person who hears about your upcoming trip and proffers a list of can’t-miss activities, unprompted. What’s that? You’re visiting a town I spent two nights in during spring 2005? You have to visit this trattoria with the best risotto my ex-boyfriend has ever tried. 

I don’t, actually!!

One of the most wonderful things about travelling sans agenda is that ignorance is bliss: You cannot regret missing what you never planned on doing! 

Our star-spangled American minds struggle to embrace unstructured time because we think it’s time wasted. But I got so much out of our trip by throwing it to the fates. If Dave and I had stuck to a daily plan we never would have had the freewheeling experience we did: Chatting with one wine bar owner in Perugia led us to another wine shop in town, where we met and befriended the owners, who then hosted us for dinner. A random connection of Dave’s recommended a tiny deli and wine shop in Bologna where we hit it off with a group of women and spent the night yapping and eating incredible tigelle sandwiches. 

The list goes on, but the point is that keeping it simple made it unique: Plop down, strike up a conversation, go where that leads. In a land we’ve never visited before, we weren’t about to act like the experts.

I’ve probably frustrated friends and family when they’ve asked about the trip and I can’t easily launch into a concise summary featuring key highlights: My Italian Vacation Cliffs Notes (sorry to my younger readers who do not get this reference!). But I’ll happily have a conversation about why I wasn’t that blown away by the food, about how the Catholic church seems to still loom over the country, and I would LOVE tell you what I learned about the reclamation of old vineyards. I took limited and mediocre photos, but I did come home with a burning desire to become a moka pot person and open a teeny natural wine bar. I’d rather a trip change my outlook than my Instagram grid (OK, this line actually reads like something you would see overlaid on a photo of a beach or mountain on Instagram, lmaooo).

I don’t think there is anything wrong with an itinerary, nor will I judge someone for wanting to hit certain places of interest. But I do wonder if we prioritize and schedule these things because we are legitimately curious about them, or if we just feel like we’re supposed to do it. When I first moved to Chicago and I would host visitors, people insisted on heading downtown to see the Bean and eat deep dish pizza. This always felt a little off to me, and I realized it was because this felt like the Disney-fied version of the city. If you want to experience Chicago, you go to the neighborhoods and do as the locals do (this also means eating tavern-style pizza, not those thick-ass crust pies).

When I’ve talked with locals when I travel — domestically and abroad — I also benefit from learning what not to do, or how to be a little more respectful. Many years ago, post-Hurricane Katrina, I hadn’t yet learned how much New Orleans residents discourage Airbnb rentals until I got to chatting with a local. Someone’s hometown doesn’t exist for your scrapbook! People live there. Just because you want to film a TikTok about a cute little coffee shop you “discovered” does not give you the right to slow down a commuter who stops there for their pre-work cuppa!!

If you feel the gripping desire to visit a fortress, go for it. But consider spending a day or two without a gameplan. Let the place you’re visiting — and its residents — be your guide. The likelihood that you’ll collect stories instead of duty-free souvenirs is pretty high (again, I apologize for unintentionally writing a travel influencer).

Three years ago, Dave and I befriended the owners of a bar in Nazaré, Portugal, who insisted on taking us to a music venue they love. Let me tell you: There is no tourist trap that can compare with the memory of a metal-head Portuguese man grinning at Dave and I, thrilled with himself for taking us to see a Pearl Jam cover band and sending us home with some unidentifiable liquor in a skull-shaped bottle.