Because of the usually rough (sometimes extreme) sea conditions in the area, Cape Horn belongs to the golden pages of marine history, being part of numerous legends and traditions. Sailors who had rounded the Horn were entitled to wear a gold loop earring — in the left ear, the one which had faced the Horn in a typical eastbound passage — and to dine with one foot on the table.

From Wikipedia:
Cape Horn is the most southerly point of South America, and marks the northern boundary of the Drake Passage; for many years it was a major milestone on the clipper route, by which sailing ships carried trade around the world. However, the waters around the Cape are particularly hazardous, owing to strong winds, large waves, strong currents and icebergs; these dangers have made it notorious as a sailors’ graveyard.

The need for ships to round the Cape Horn was greatly reduced by the opening of the Panama Canal in 1914. However, sailing around the Horn is widely regarded as one of the major challenges in yachting. Thus, a few recreational sailors continue to sail this route, sometimes as part of a circumnavigation of the globe, and almost all of these choosing routes through the channels to the north of the actual Cape (though many take a detour through the islands and anchor to wait for fair weather to actually visit Horn Island or even sail around it to replicate a rounding of this historic point). Several prominent ocean yacht races, notably the Volvo Ocean Race, the VELUX5OCEANS and the Vendée Globe, sail around the world via the Horn, and speed records for round-the-world sailing are recognized for following this route.

Full article here.