The summer in the late nineties I spent with a Eurail Pass and the contents of a single backpack, I took pride in never booking a place to stay ahead of arriving. This meant, most often, that I ended up in the hostel that hit the best ratio of not-gross to train station proximity. The approach usually served me well, and it gave me some of my best adventures, a day spent eating baguettes and cheese and drinking wine in that park next to the Eiffel Tower while waiting for a night train, a night spent drinking around Dijon instead of paying for a room, while waiting for morning train. One time it meant that I accidentally woke up in Vienna instead of Prague—the overnight train had split sometime in the early morning hours, and it was the other half that made it to my intended destination. No matter, I hadn’t booked a place, so no harm done.
I arrived that summer to Krakow, Poland one evening, maybe around 9pm, to a downpour. I don’t remember how, but I quickly learned that every hostel listed in my guidebook was fully booked. I ended up paying $50—an ungodly amount for me that summer—for a hotel room. It was a wonderful hotel room, with creaky wooden floors and a writing desk and a window that let in that yellow light that only exists in European cities at night. It was the best place I stayed that whole trip, the loneliest and the most attuned to whatever I thought I was becoming then, at age 22. I’m sure I wrote in my journal that night. I checked out the next morning and vowed to make up for the expenditure with the cheapest place possible the following night.
That place ended up being a room in the communist-era apartment of an old Polish woman who spoke five or so words of English. At the time, it was common to book such rooms through an agency in town. Today, it’s probably all done on AirBnB.
By the time I got to the apartment, which was located on the outskirts of Krakow in a depressing collection of buildings made more so by the rain, I’d also come to understand that not only was Pope John Paul II in town, he was also back in his hometown. This was an enormous deal to the city of Krakow, and the reason all the hostels had been fully booked. No booze could be served anywhere in the city during his stay. If you have ever been a 22-year-old with a Eurail Pass, or known one, you know that booze is the central thing to the experience. I was adrift.
At the apartment where I stayed, I sat in the living room with the old woman and watched the Pope make his way around Krakow on an old TV. She was extremely proud and because I could tell as much, I sat with her for quite a while. I don’t remember much about that living room, but I do remember that she was sitting to my right and that the TV was in the corner next to the window. Gun to my head, I’d say pink was a dominant color in the décor. I don’t remember the bedroom at all.
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In my early thirties, I went to Spain and Portugal with my mom. We arrived first to Madrid, where my mom had booked a hotel room with curtains that, we discovered when we entered, matched her shirt almost exactly. Later in the trip, we flew to Lisbon, and after a couple of nights, made our way south via train (or was it bus) to Lagos, on the southern coast of Portugal. I insisted that we not book a room ahead of time, out of some combination of loyalty to the way I’d traveled in my twenties and desire to prove to my mom how fine everything would turn out if we flew by the seat of our pants.
We got to Lagos, sat outside a café and drank coffees, and then I left my mom there to relax while I went in search of a hotel room. I found one, and it all went fine. Was it a more fulfilling experience for having been unstructured? Who can say.
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I spent this past fall in Southeast Asia, drenched in a perpetual summer. After the first three weeks of the trip, I traveled mostly alone, and I remained mostly on the go, rarely staying in a particular hotel for more than two or three nights. I always booked ahead. I can’t attribute this to the part of the world I was in, since nine years previous, I’d also traveled this part of the world and booked ahead only my first night in Bangkok, a place to crash after my flight got in at 1:30am.
That time, an incredible rain descended on Bangkok the morning after my arrival, turning the street into a river and trapping me inside this dreadful hotel. Early afternoon, I booked another night there thanks to a true lack of options. A couple of hours later the rain stopped and the floods faded away. Street vendors returned to their spots to clean up, stepping around enormous drowned rats. The next day, I left on a bus for parts further south. The bus let me out many hours later in Krabi and, because I wasn’t sure of my destination, I stayed a night there, in this mainland town that is almost always overlooked in favor of the magnificent nearby islands. I took a boat the next day to the nearest place offshore, Railay. It would become one of my most treasured travel destinations, with perfect beaches and heavenly snorkeling and monkeys in the morning and bioluminescent water at night.
And still, the story fluctuates between serendipity and bad luck. My first night in Railay, I walked up a jungle path and booked a cabin for $5. This was the worst accommodation I’ve ever slept in, and the next morning I decamped immediately for a $25 room with air conditioning and clean sheets.
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I didn’t have any experiences like this on my recent trip. I never, in fact, slept without air conditioning. I did waste a lot of time in one place perusing accommodation in the next, however.
Booking ahead works differently now, of course. As recently as ten years ago, it was still necessary log into a good internet connection to get anything done. If I was mid-trip, the path of least resistance was to just wait until I got to the next destination and then poke around. On this recent trip, on the other hand, I had a data connection in my hand at all times. I had a million blogs and user reviews to look through to find the spot that would do best by me, and the apps installed on which to book them.
I notice that the places I slept in 2017 take on a larger role in my experience than those I stayed in years ago. This time, I slept in historic buildings and swam in destination pools. I posted Instagrams of these rooms. I took cabs to them straight from the airport, and then popped a beer from the minibar. I read books on terraces and had conversations with the staff. As I get older, the hotel is no longer just a place to dump my stuff and then, much later in the night, crash out. The hotel, instead, has become part of the journey itself.
