There’s competitive sailing, and then there’s the kind of sailing that makes even seasoned mariners question their life choices. Some races cross entire oceans, others plunge competitors into the brutal waters of the Southern Ocean, and a few have earned reputations for storms, shipwrecks, rescues, and tragic loss of life. While modern technology has made offshore racing safer than it once was, these events remain among the most demanding sporting challenges on Earth. Here are some of the most dangerous sailing races ever attempted.