Where do you start? Wherever you are. Step outside your hotel, train station or B&B into a new country, city, town or village and proceed to get thoroughly, discombobulatingly lost. It's the only way to travel.
Get thee away from us, Google Maps, with your little blue dot and your "27 minutes" to walk there, and "13 minutes" to drive. Instead, we will aim in the general direction of the market, gallery, museum, restaurant or river and see what unfolds. Because something always does.
It's actually difficult to get genuinely lost these days, what with satellite-based radio navigation systems, maps, signposts and helpful locals. We know where we are, all the time. It's why we pay to get lost in a maze, because everything else in our lives is tracked by GPS. But we shouldn't lose our own innate ability as humans to look to the sun and the shadows to know where we are. If nothing else, get lost because it's good for your cognitive development, fizzing and sparking new neural pathways that will protect you against impairment and disease.
Sometimes, the road less travelled can be so for good reason. The gradient is so steep from one street to the next in parts of Hong Kong island's Mid-levels, that the locals prop ladders against walls to help them get from A to B. The back streets of Naples, hung with laundry like a Coronation Day street party, can be rough, with muggings not uncommon. (And sure enough, I was set upon by a local, who insisted on escorting me gently away from the district so I didn't lose my camera to his neighbours.)
But the real joy of stepping off the tourist circuit is surprise. Plan your day with great efficiency to tick off as many sites as possible, and you will have the same experience as every other tourist in town. But just go walking or cycling, or take a suburban train to the end of its line, and give it time to see where it takes you. Suddenly you have a more personal, intimate connection to the place and its people. My friend D. is forever getting lost, and not once has it bothered her. She has such a strong belief in the rules of the universe, that the universe rewards her by sending her new friends and memorable experiences.
And when you get really, truly, confusingly, heart-racingly lost? Embrace it. Surrender unto it. Sometimes, finding what you are not looking for, can be just what you are looking for.