Key West is notably a top-notch vacation destination for people across all ends of the spectrum who want to experience their own piece of island paradise. Whether you aspire to spend most of your time on the white sandy beaches with the occasional dip into the cool crystal clear waters, or you are wanting to delve into the culture of the locals by visiting historical and popular hotspots, the island provides a versatile experience for everyone.

However, much like any timeless destination, Key West evolves with the seasons, providing various festivities and events that occur during specific times of the year. These events have become so renowned, in fact, that some people visit solely to engage within the lively atmospheres associated with them. As someone planning a trip to Key West, consider reserving your visit for one of these popular events for an experience that comes around only once a year.

Key West New Years Eve – The Drop of The Red High Heel

Who doesn’t love a good New Year’s Eve party? This festive time of the year brings out the cheer in all of us – creating that burning sensation to spend a few hours drinking, mingling and eating, all while ringing in the new year. And while you may have been to some rowdy New Year’s events in the past, none will compare to the smorgasbord of fun-loving crowds that gather on Duval Street to watch the red high heel drop. With a welcome barrage of open bars, diners, cafes, and street entertainment, you will have no problem keeping that whistle wet and stomach filled to the brim, all while enjoying the festive atmosphere that is classic Key West.

Key West Boat Races

When early November rolls around on the island of Key West, there is only one thing on the minds of locals and visitors alike: raw horsepower hydroplaning over water. The Super Boat International races are an annual event that features some of the fastest watercraft in the world, attracting large crowds with the occasional celebrity racer. If you like the roaring sound of a powerful engine, or just appreciate the impressive speed that these magnificent crafts can reach, it may be worth adding to your “to-do” list.

Ernest Hemingway Contest

As part of the famed Hemingway Day’s celebration, the Ernest Hemingway Look-Alike Contest is one of the most popular events that takes place during this time of honoring one of America’s most pivotal authors. Held for nearly three decades at Sloppy Joe’s Bar, this contest brings together the most potent supply of portly gray-bearded men the world has ever seen. Contestants bout it out for the acclaimed title, trophy and cash prize. A truly entertaining and noteworthy experience that above all else, is free to watch.

Fantasy Fest Key West

Held during the last week of October, Fantasy Fest has become a favorite that attracts visitors from all around the world. Best described as one big street party, each day is lined with many unique events that reflect the diverse culture of the island. From all-night parties in some of the most popular bars and clubs to pet masquerades, there is plenty of activity to keep even the most reserved of visitors intrigued. If you enjoy the buzzing atmosphere of a massive party that simply does not seem to end, you may consider visiting Key West during Fantasy Fest.

Key West is simply one of those highly sought after vacation destinations that keep people coming back for more. As part of your continuing love affair with this majestic island, ensure you get your fill of the events in Key West you don’t want to miss.