Every evening, about an hour before sunset, the crowd begins to gather at Mallory Square. By the time the sun touches the Gulf of Mexico, the dock is packed: acrobats, escape artists, a trained-cat act that has been performing for decades, cookie vendors, artists selling watercolors of the very scene in front of you. And then the sun goes down, and everyone applauds.
It sounds like a tourist trap, and it has some of those qualities, but it is also genuinely communal and genuinely beautiful. Even locals show up some nights. The light on the water as the sun drops is extraordinary, and the atmosphere — warm, slightly drunk, entirely relaxed — is quintessentially Key West. It is free, and it is one of the better things you will do on the island.