Maroantsetra, Madagascar

This tiny coastal port town is not for the faint of heart. With just 42,529 residents, Maroantsetra played an outsized role in the tumultuous history of the Betsimisaraka tribe, serving as the site of their unification. However, the town's isolation and the region's notoriously poor transport links are a persistent headache - the unpaved National Road 5 linking it to the larger city of Toamasina is in "notoriously poor condition." And the heavy rainfall, averaging 138 inches annually, makes travel unreliable. Maroantsetra's role as the gateway to Masoala National Park and other natural wonders may appeal to the hardiest of adventurers, but for most, the bureaucratic and logistical challenges will likely prove too much.