When travelling around the Americas, your route options are quite straight forward – South to North or North to South. Regardless, if you’re planning on making either journey without flying, then the most obvious place to cross continents would be between Panama and Colombia. The ferry from Colombia to Panama was cancelled some time ago. As a result, the most common (and enjoyable) way of making the journey is by sailing Colombia to Panama by sail boat. I met a lot of travellers who talked about this being the highlight of their South America backpacking trip.