Out of Eden Walk
Anyone with an interest in slow travel will enjoy the dispatches of Paul Salopek, a Pulitzer Prize winning journalist who is walking around the world as part of a project sponsored by National Geographic. He stays right on the ground and generally avoids tourists and big cities. The project is designed to trace the steps of early humans from their original home in Africa, and to last seven years.http://www.nationalgeographic.org/projects/out-of-eden-walk/
Salopek is not travelling alone, but with a substantial amount of equipment, a local guide and sometimes pack animals such as donkeys or camels. His reports are immediate, and through his guide/translators he is able to interview locals he meets en route. At present he is in Uzbekistan.
His reports are quite erudite, with on the ground observations supplemented by a deep knowledge of history and culture. So for example in reporting on Khiva, one of the most famous stops on the Silk Road, he goes into a lot of background on the museums and libraries of early Islamic scholars and scientists who lived there.
His trip is designed to take seven years. It is accompanied by an international learning component, available online to students and educators around the world. This seems to me like a great way to learn about history and foreign cultures.
As for replicating parts of his trip on your own, I suspect it would take an enormous amount of planning, guts and money. But what a trip it could be.