Another reason to move to the Destin area is Pirate Festivals. Fort Walton Beach holds the Billy Bowlegs Pirate Festival every year.
The Billy Bowlegs Festival grew out of a Labor Day ski show celebration back in 1953, which was the brainchild of some enterprising young businessmen, the JAYCEES, eager to latch onto a project that would warrant their time and efforts, be fun, and bring more tourists into the area. The idea of a Gasparilla-type observance centered on a “pirate” theme, and they unanimously chose as their patron pirate the notorious and legendary William Augustus Bowles, a pirate of controversial authenticity whose alleged dastardly deeds were widespread throughout the area. Nathan Fleet, a downtown Fort Walton Beach retail merchant at that time, was chosen as the first Captain Billy Bowlegs to reign over the Festival and lead the pirate “raids.” (In later years, his son, Judge Erwin Fleet, reigned as Cap’n Billy XIV.) The overwhelming success and acceptance of the initial celebration sparked great enthusiasm and interest among other businessmen of the community. A small group of merchants, of which two, together with two from the JAYCEES, were secretly delegated to choose from the member list the Billy Bowlegs as reigning pirate of the three-day festival, his identity to remain unknown until the unmasking ceremonies took place on the evening of the grant ball. Due to the huge success of the festival, events were added such as treasure hunts - typically the most popular part of the entire festival, but inexplicably eliminated in 2009 - parades, gigantic fireworks displays, athletic events, a landing to include the townspeople with the “capture” of the City and the hoisting of the Jolly Roger to signify the total surrender of the City. Beards were grown, costumes made, and over the years became more elaborate. Professional floats were added to the Grand Torchlight Parade and a glittering Coronation Pageant, open to the public, at which a new Cap’n Billy, his queen, a first mate and his lady, ten honor guard couples and children of the court are unmasked each year, with a private ball and midnight breakfast for Krewe members and honored guests climaxing the now week-long festival. Thus a tradition was born: The Billy Bowlegs Festival, with the infamous Krewe of Bowlegs and its current Cap’n as the “Star” of the show.