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Events and Festivals in Key West Florida

Key West's Most Popular Festivals & Special Events

There is an abundance of popular Key West Events and Key West Festivals
that are held throughout the year on this island playground.  Key West
Florida is one of the most unique tourist destinations to be found anywhere 
when it comes to fun events and festivals to take part in. 

The island plays host to a number of large events and festivities that will satisfy the interests of just
about everyone, whether you're a tourist or a local.

We'll start with the cities most popular attraction and grand daddy of all festivals, Fantasy Fest.  Fantasy Fest is a ten day crazy and extravagant festival of events held each October that really get's this little island paradise rocking and rolling.  Click here to view the official Fantasy Fest website.

Every bar and business in town sponsors some sort of event in celebration of this popular event.  Reserve our Condo Rental early if you plan on attending this most popular attraction.

The week starts off with the Goombay Festival in the Bahama Village part of town.   Goombay is a music played with African drums that the Carribean and the Bahamas is so famous for.  It's tradition dates back to ancient times in Africa and Key West is one of the only places in the World to celebrate and carry on the Goombay tradition. 

The event features exotic costumed Goombay dancers who travel the street and entertain their guest.  Street vendors are every where with great food, many feature original arts & crafts that will make grandma feel like she's arrived in heaven.

During Fantasy Fest week the islands numerous bars take center stage with a line-up of wild events that you won't want to miss.  There are too many events to mention in this article so we will focus on the most popular attractions.  

There is Captain Tonys Party in Plaid event that features everyone wearing plaid of course.  The kicker is that guests are encouraged to wear something naughty which is when the fun really starts.   The Key West Wild, Wild West Party at Cowboy Bills is another fun event that can get a little nuts as the night goes on. 

There's the Lazy Gecko Redneck Party held at the Lazy Gecko Saloon that is hilarious with prizes awarded to the biggest Redneck, best Redneck Mama and Redneck couple.
Event calendar.

Don't Miss Sloppy Joe's Famous Toga Party!

One of the weeks events you definitely won't want to miss is Sloppy Joe's Toga Party.  Patrons are encouraged to use Fantasy Fest themes and prizes are awarded for the best costumes.

This event is loads of fun.  A close second to the toga event is the Hair of the Hog-Leather and Lace Party held at the Hog's Breath Saloon.  You won't want to miss out on this fun event if you're in town that week.
Sloppy Joes Bar.

Featuring Some of the Best Key West Adult Entertainment!

For those thrill seekers who prefer the naughtier adult entertainment, Key West's Fantasy Fest will not disappoint.  There is the Dungeon of Dark Secrets & Fetishes featuring leather, latex, voyeurs, burlesque and an any thing goes theme.  It's held in the Bourbon Bar Saloon and the entry fee is a modest $20. 

The Bourbon Bar also hosts naughty weekly events throughout the year.  Next on the list is the Swing & Skin Freak Fest event held at the Bare Assets strip club on Truman Ave.  There are porn stars, pole dance competitions, exotic dancers with a limited number of tickets available to the general public.

Bloody Marys and world famous breakfast burritos are par for the course along with cash payouts for the best dressed guest.  And of course no one wants to miss the Annual Pirate Bash held at the Rum Barrel.  The event features great music, fantastic rum deals and cash prizes and it takes place on the rooftop stage!
The Wet T-Shirt competitions at Dante's and Cowboy Bills are both fun events that can get rowdy and features pole dancing, body painting and cash contest for the ladies.  Key West is also known for it's many gay themes. 

For the guys you may want to attend the clothing optional Fetish and Fantasy Party held at the Island House on Friday.  There is also the Pimp & Ho Party hosted by porn star, Ron Jeremy.
Wet T Shirt competition at Key Wests Dantes Pool & Bar.
The event features a costume contest and exotic dance contest.   We warn you, don't bring the family to this fun event, which is always a sellout. 

The Fantasy Fest week doesn't officially end with what is considered the grand finale of the week, the Captain Morgans Fantasy Fest Parade, but the fat lady is close to singing after this amazing extravaganza.

There are over seventy thousand plus patrons taking part in this gigantic parade.

There are exotic floats, bands and dancers, many of whom are adorned with nothing but body paint for attire.  This event is possibly the wildest and craziest parade in the world and it's a fitting finale for an amazing week of frolicking.
Another famous event in the gay community is the week long Womenfest festival held in Sept.  The event features loads of activity for the ladies including: many outlandish clothing optional parties, comedy shows, dance contests, great music, food and the list goes on.......

If you're a Jimmy Buffet fan then you're definitely in the right place.  The island is famously known as the home base for this famous entertainer/song writer.  Each November Key West hosts the Annual Meeting of the Minds. 

Each year thousands of Jimmy Buffet Parrot Heads flock to the island to celebrate the islands tropical theme and pay homage to their inspirational music leader.   In 2011 Jimmy even made an unannounced guest appearance and held a impromptu concert for his adoring fans.

There are loads of activities during the week and it's one of the islands most popular events.
In November Key West also plays host to the World Championship Power boat Races.   The fastest boats in the world gather for this exciting but dangerous event.  The event is the NASCAR version on water.  There are many areas around the city where spectators can watch the race. 

In 2011 the racing sport saw tragedy and we were reminded how dangerous the event can be when  two of  the veteran racers died on the first day of competition.
Powerboat competing at the Offshore Key West Power Boat race.
Yet another big event held in January each year is the annual Key West Sailing Regatta.   The event lasts for five days and attracts sailing enthusiasts from around the globe.

In June there's a popular nine day long event called Pridefest.  The festivities are numerous for the event that celebrates the diverse culture that Key West is known for.  There are dance parties, water activities, street parades, adult competitions (not fit for the entire family), films,  with plenty of good music and food.

The annual Songwriters festival is another favorite event that's on the entertainment list of fun things to do.   There are over one hundred world class musicians and entertainers from around the world who get together to jam for this five day event, which is held on the first part of May each year. 

There are over 30 stages in use where these aspiring artists and song writers will entertain you during this one of a kind music festival.

If you're a Harley Davidson enthusiast then the annual Phil Peterson's Harely_Davidson Poker Run could be the event you wouldn't want to miss.  The event features over ten thousand riders from across America who gather in Key West each September to support this great charity event. 

The city blocks off Duval Street for throng of riders who attend this fun event.   It's a party atmosphere from the minute you arrive until the last rider leaves.   This is truly Harley Heaven.

For those tourists who are on the fitter side of life there's an event in September that could be just the activity you've been looking for.  The Swim Around Key West competition consists of a 12.5 mile race around the island that attracts swimmers from around the planet. 

The race is for anyone between the ages of eighteen to sixty five.   Couch potatoes need not apply.

There are numerous other
Key West attractions and events that are worthy of mention, such as the week long Hemingway Days Festival held each July or the Pirates in Paradise Festival, held each December. 

For a complete listing of events you can check out the Key West Chamber of Commerce schedule of events website.
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