Key West first started to become a major tourist destination in the 1930's. Faced with having to declare bankruptcy - for the second time - the Federal government chose to send down artists, writers and painters to sell the island as America's Caribbean destination. The first tourist attraction, the Aquarium, was built at this time and still entertains people to this day. At the time, people mainly flocked there during the winter months. From January through April the weather was mild, the humidity was low and the bugs were nowhere to be found.
The other eight months proved to be a challenge when it came to drawing people. Although this made it tough for some people to make a living, as they tried to stretch their money through several lean months, other people on the island began to embrace it. It gave them the opportunity to live as they wanted to without anyone else caring. One of the first events that was formed during these off months was Fantasy Fest.
Originally formed as a combination Halloween party and AIDS fundraiser and memorial, they chose the date - the last weekend in October - because there was nothing else that would conflict with it and it could be a reasonably private affair. Today, almost four decades after it was first celebrated, it has become the most popular week on the island, drawing nearly 100,000 people. But it is hardly the only off-season event that draws a crowd.
A couple of weeks before Fantasy Fest is Bike Week, when over 10,000 motorcyclists ride into town. Immediately following Fantasy Fest is Meeting of the Minds, the annual convention of fans of Jimmy Buffett, also known as parrotheads. That week is followed immediately by the grand finale of the powerboat racing season, making for the busiest three week period of the year outside of spring break.
It is not just in the fall that these events happen. Just last week was the annual Hemingway Days, celebrating the life of Key West's most famous author. Earlier in the month was Mel Fisher Days, and other events in the summer include Lobsterfest and Battle of the Bars.
All of this means that it does not matter what month the calendar is on and when your friends say you should go on a tropical vacation. Anytime you want to experience all that the southernmost island has to offer, including award-winning Key West restaurants, stunning sunsets, beautiful coral seas and exciting nightlife, there is always a good time waiting to be had. As one local musician sings, "Every night is a Saturday night, every day a perfect ten." You want to know the best time to go on a tropical vacation to Key West? Right now.
Jack Terry is a freelance travel and lifestyle writer who has lived in Key West for several years. http://www.rooftopcafekeywest.com