Reading the letters or diaries of people who were bold enough to travel the world, is often a historically rewarding experience. There is a short book translated as Pathways to Jerusalem: The Travel Letters of Rabbi Ovadiah of Bartenura which personally was quite interesting. Bartenura wrote one of the two classic commentaries on the mishna that is still studied by most schoolchildren and anyone else seriously studying the mishna. He was originally from Italy (in the late 1400’s) and in a few letters to family and friends he describes his journey from Italy to Israel. Needless to say the journey was perilous. The letters describe medieval Jewish Messina, Palermo, Venice, Syracuse, Alexandria, Rhodes, Cairo, Cyprus, Jerusalem, Demascus, Gaza, Sefad, Hebron and other places.
The relationship between Jews, Christians, Muslims, and Mamluks is discussed. Nuances about the types of food they ate, the prices that one paid for things, how commerce was done, and how synagogues were run are all included. It is a historical treasure, and a nice read.
Also, the translation by Yaakov Dovid Shulman seems competent. It would be nice to have a more extensive historical background and introduction to the letters though.