Freebooter's Folly is an annual race held by the pirates of the Blacksand League. A test of both speed and endurance, the route of the Folly takes its participants around the many islands of the Blacksand Archipelago. To win, pirate crews must be able to maintain a breakneck pace for days as they carefully navigate the Folly. One of the most dangerous sections of the Folly takes the participants through the gap between the Two Halves - inevitably, every year multiple ships crash when traversing this narrow passage.
The winning crew of Freebooter's Folly is granted a large payment of gold pooled by the main factions of the Blacksand League. Such an achievement also brings with it a great deal of prestige and standing amongst the pirates.
Damaging other ships during the race is disallowed but this rule is rarely enforced. Privateers of the Kilche Sea have taken to picking off straggling racers during the event, holding back until the pirates have impaired each other first and left themselves unable to escape.