I love to travel alone for one very particular reason: the strangers I meet. The conversations we have and their unexpected turns send me deep into the places I go, far beyond skimming the surface lightly. I talk to people who live there, travelers, anyone with a story, anyone who may turn my path a different way from what I had planned. These encounters are what cement my memories of a place, and my relationship to it.

Once on an overnight train from Frankfurt to Milan, I shared a cabin with a prim German woman from outside the city, maybe in her 70s, clutching a newspaper. As we waited for the train to depart, I said hello. I asked her if it was a good newspaper, and got a rundown of the merits and failures of a dozen publications. Soon we settled into our separate preoccupations to signal the end of the conversation. I was in the wrong time zone. I fell asleep before the light faded.

Hours later, I woke up to a gentle nudge and a whisper. “Are you awake? You must come down.” She beckoned me to the window. The train was on a slow arc around the shore of a vast black lake. There were a few towns like scattered bits of moonlight, broken loose from the great glowing strip across the still surface of the water. Hard by the edge of the lake, a mountain in the form of a massive shadow rose up into the charcoal mist. “It’s Lake Como,” she told me. “It’s terribly expensive here now. But my sister-in-law has a small place that was left to her by her godmother. We visit sometimes. I would stay forever if I could.” She paused; I waited. “What a moon. Isn’t it the most beautiful thing you’ve ever seen?”

It was, and it still is. And had I not made a small connection with her, I would never have seen it. She would never have thought to wake me, never dropped her formality and spoken wistfully of her wishes.

Talking to strangers along your travels can change your trip into an adventure. It can take you into the unknown, unexpected hearts of places and people, trading what is planned and predictable for what may turn out to be sublime. One note: This is territory for adults to traverse — an important caveat is that it is not for children or teenagers.

Here are five rules of thumb to guide you into such adventure.