When Spain commissioned Ferdinand Magellan to find a westward route to the Spice Islands in 1519, the explorer commanded five ships and 240 men. Six years later, nearly every member of the expedition, including its commander, was dead. When the American writer Jack Kerouac tried in 1951 to find the words to convey his wayward journey through the United States and Mexico, he commanded a typewriter and a massive stash of Benzedrine. After a few weeks, the first draft of On the Road was completed. These are just two of the journeys that have left indelible marks on our collective maps, and are endless sources of fascination. Here is compilation of some of the most famous jaunts of all time-both factual and fictional-that show us how far we've come, and where we might go next.