Longtime readers of travel writing might sometimes find themselves incredulous at the number of adventures that befall the author during their journey. Of course, uneventful days will rarely make it to print, but those writers have also likely unearthed the essential secret to exploring a city: The more doors you push open, the more likely you are to discover something interesting.

Sometimes, the door-pushing can be literal. You could, for example, happen to be wandering around the cemetery island of San Michele in Venice and hear the incongruous sound of cheery voices. Pushing open the door of what used to be a monastery reveals Laguna nel Bicchiere—a historical vineyard, where, with the help of Google Translate, you can soon be sampling the previous year’s vintage with the lagoon’s winemakers.¹

Cities can often be places of unexpected contrasts. For a traveler exploring any new place, a good approach is to embrace some contradictions of your own. You’re somewhere unfamiliar? Do things you’d do at home. Struggling to orient yourself? Deliberately get lost. Don’t know anyone? Act as if you do.

Books can be a guide, but don’t just stick to guidebooks. Try to read a novel set in the city. It probably won’t tell you where to eat, but it might give you a sense of how the city’s people eat. It could also suggest a starting point for your interpretation of the city: a historical event on which to focus, or a character through whose eyes you can see the streets.