In 1956, as a nineteen-year old university student, the author and a companion set out on a two-month-long journey around the eastern Mediterranean. A unique feature of the trip was their decision to hitchhike. The journey began in Madrid, Spain. War, and the threat of war, posed barriers to a continuous land-based effort, inspiring them to book passage on tramp steamers plying the Mediterranean whenever the need arose. Less than a dozen years after the Second World War, it was a time when Americans were well received wherever they went. It was also a time when university students, of all nationalities, were held in high regard. Capitalizing on these two sentiments, the author and his companion navigated the treacherous currents of cultural misunderstanding, rigid officialdom, and language, to arrive at their intended destination - Istanbul, Turkey - just as planned. The memoir recounts their adventures hitchhiking down to Sicily, deck passage to Malta and on to Benghazi, Libya, hitchhiking across North Africa, taking deck passage to Beirut, hitchhiking through the Middle East, and finally boarding the famed Orient Express in Istanbul, Turkey, for a memorable train trip behind the Iron Curtain.