Photo: Punnawit Suwattananun/Shutterstock

Why You Should Burn the Itinerary for Your Next Trip

Insider Guides
by Eben Diskin Oct 31, 2017

“What cities will you visit? How long? Will you rent a car? Where are you staying?” I can’t remember the last time I traveled and didn’t hear these questions. I used to have answers for them all. “Prague, Vienna, and Budapest. Two nights each. The train. A hotel two blocks from Prague Castle. On Vorgartenstraße near a park. Right around the corner from Szimpla Kert.” I always knew where I was going. I always had answers — and I got sick of having answers. Quickly, I learned that even the most inventive agendas can turn into prisons. If you really want to have a memorable trip and get a great reaction out of your friends in the process, then when they ask, “Where are you going? Where are you staying?” just say, “I don’t know.” And mean it.

Feeling lost is wonderful.

I only truly realized the dangers of having an itinerary when I took my first trip without one. A friend and I had rented a car in Iceland to circle the Ring Road, the single highway that connects the entire country. Since we couldn’t predict how far we would get on any given day, we decided not to book any hotels in advance and just figure it out last-minute. By not locking ourselves into bookings, we were free to linger at the waterfalls, geysers, and canyons, without worrying about having to “show up” somewhere on time.

One afternoon, we booked an Airbnb at a horse farm in the middle of a valley. We expected to arrive around 10pm, but after a full day on the Ring Road, it was more like 1am. Directions from our host were vague at best. “Second farm in the Vatnsdalur valley. West side of the river. Magnus will greet you.” Thankfully it was July, so even at 1am there was still a grayish light in the sky. We drove through the valley twice. Was it the right valley? We thought so, but who really knew? Were we west or east of the river? Was Magnus the hulking, angry Thor-esque farmer we imagined? Finally, we pulled into a horse farm and knocked. No answer. It was unlocked, so we went inside and looked around. Clearly, if Magnus lived here he was asleep. There were three doors ahead, and one was ajar, so we peeked inside and saw two empty beds. More important than that, through the window we noticed a hot tub outside the room. Five minutes later we were looking out at the river under a midnight sun, in what was very possibly not Magnus’ hot tub at all. The next morning we left without ever meeting our host. If I had planned ahead and booked a hotel, we might not have accidentally trespassed in an Icelandic farmer’s hot tub. But on the downside, we might not have accidentally trespassed in an Icelandic farmer’s hot tub.

Mistakes pay off.

It’s pretty easy to “wing it” when you’re in Italy. Lush hills and green mountains are around every turn, and seemingly the whole country smells like jasmine. We did, however, manage to take several wrong turns, most notably while trying to find the Ruins of Pompeii — an excursion we had devoted all of five minutes to planning. We were heading north from the Almafi Coast, and decided to see the ruins on the way. We plugged “Pompeii” into our GPS and a pin came up. When we arrived, it didn’t seem quite right. The buildings in the bustling city were modern—not heaps of debris, as we expected—and the people weren’t petrified pillars of plaster. We walked around for an hour asking, “where is Pompeii?” If they spoke English, they would answer, “This is Pompei! You are here.” And if they didn’t, they would just shrug and try to sell us gelato. Eventually, we did find the ruins, and though the mixup would have definitely been avoided by more prepared travelers, spending an unexpected afternoon in modern Pompei (we didn’t even know there was a modern Pompei) turned out to be one of the more memorable, amusing moments of the trip.

Nothing beats going off the grid.

Not until my Balkans road trip could I genuinely say, “We’re landing in Bulgaria, driving through seven countries, and somehow getting back to Bulgaria 10 days later. Not really sure about the in-between stuff.” It was true. Besides pointing to some unpronounceable city names on a map and saying, “yeah, we should probably check that out,” we hadn’t planned anything specific. After passing through Serbia, Bosnia, Croatia, and Montenegro, we had planned to head back east, through northern Albania to Macedonia. Problem was a few days earlier, 200 protestors had stormed the Macedonian parliament and attacked lawmakers, and we had heard rumors that borders would be closed to all foreigners until the situation was under control. The uncertainty was definitely nerve-wracking, but it was also exciting. Since we hadn’t booked any hotels in Macedonia and had no concrete plans there, we really could go anywhere we wanted. We considered heading north through Kosovo and staying with a friend of mine in the mountains, or going all the way south through northern Greece. The freedom to get creative with our route relieved us of a lot of anxiety.

Luckily, the borders remained open, and we passed easily into Macedonia. Since we wanted a more rural flavor, we went north to Mavrovo National Park, having hastily booked a guesthouse from the road. We arrived at the house of a lazy-eyed farmer, who spoke no English, and promptly made us a traditional sausage and veggie dish. We had expected there to be some forest trails or hiking paths, but there were only a few dirt roads with farmhouses, and long fields beyond. As it turned out, this little town — if it could be called a town — was more interesting than any hiking trail. A quick stroll brought us to a small church, a private creek, and several houses without walls, damaged decades ago by bombs. Herds of brown cows shared the street with us, and seemed to look at us curiously, wondering, “of all the places to visit in this country, why here?” Well, a flexible schedule means finding yourself in places that don’t make a ton of sense, which might not show up on TripAdvisor. And that’s where the real excitement comes in. The problem with an itinerary is that if you’re not careful, you might end up following it.

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