I embarked on a mission today to find a t-shirt shop I'd heard rumor of recently. I couldn't find its exact location from the web so I figured I'd wander around until I stumbled onto it. A friend compared this approach to the gameplay in an RPG, where you can operate pretty aimlessly, prompting locals for information that can help you in your quest. It's an apt comparison, and it's become an increasingly rare mode of experiencing a place, but that's how I've typically travelled.
A trip that stands out along those lines was the one I took to the Caucasus with my friend Anjali. We were living in Ukraine at the time and were both well-traveled and opted for no preparation other than our roundtrip tickets to Tbilisi. We mostly memorized the Georgian alphabet on the flight, dozed off some, and arrived in the early morning. We had no map and nowhere to stay so we made our way downtown and to the train station, thinking we'd be able to find an affordable hotel or a babushka offering a room for rent. The hotels turned out to be too expensive - a couple hundred dollars a night if I recall correctly, or about as much money as I had to my name at the time. The clerk assured us the rooms were "very nice." The train station was notedly absent of nice old ladies offering shelter, in contrast to our experiences in other formerly Soviet republics. The city at this time was host to a disruptive anti-NATO protest, so that may have had something to do with it.
By this point it had started raining, and Anjali had placed a scarf over her head. Our search for shelter was taking on a certain Mary and Joseph quality, as we asked a woman sweeping her doorstep if she knew of a nearby internet cafe. She gave us directions as she placed a hand on Anjali and offered a sympathetic smile. Now, the internet proved to be an information desert for basic housing in Tbilisi, except for one forum post that contained the building number of a couple who offered rooms to travelers. We set out for it, though we didn't have an apartment number, so I resolved to just start knocking on doors. A woman answered the first door I tried. I apologized for bothering her and explained what we'd read, and it turned out it was her and her husband who were running this hostel of sorts. They invited us into their apartment, which I remember as open and bright, with Judaica, and explained they were already housing a group of Swedes who'd come to the area for mountain climbing. They were, however, able to ask their neighbors to house us. Fortunately those neighbors - a family of artists and musicians - were able to take us in.
It turned out to be a great experience. The walls were covered with paintings - many of family members. The mother worked restoring art at the local museum, and in our downtime we'd hear the father listening to opera or the daughter practicing violin. The grandmother told us about the city and where to find what. She also recounted to us that before Georgia's civil war in the 90s different ethnicities and faiths had gotten on harmoniously. It was a particularly poignant observation since at the time Russian forces were passing through parts of the country, as part of Abkhazia and South Ossetia's effort to break away from Georgia.