Key West's most anticipated event is the yearly festival called Fantasy Fest.  Fantasy Fest occurs every year in the last week of October, and can be described as a friendlier, safer, and more laid-back Mardi Gras.  The party culminates every year on the last Saturday in October with an enormous parade down Duval Street.  Elaborate costumes, body paint, bead exchanges, and liberal quantities of alcohol make the event fun for all who attend.  There's a schedule of activities every year that includes balls, parties, and costumes.

To be more precise for those who have never been to Mardi Gras, there may very well be total nudity (albeit under paint) and many topless females and virtually bottomless males of all ages... but in fairness: it is actually quite wholesome, if that doesn't seem a contradiction of terms or offensive for those who are very sensitive about overt displays of body flesh. While there are occasional children there, it would be best called an adult event if you are traveling in and your children have not been exposed to this type activities to feel comfortable. As for most adults: nothing is perverse nor obnoxiously in your face, unless you want to get up close and personal-with permission. All parade goers act quite natural and the crowd is very low key about "costumes". It is pure fun; you will be smiling and laughing the entire day...unless you brought you elderly religious aunt and shy 5 year old, thinking it was a nice family Halloween parade.

If you plan to attend Fantasy Fest, book early as hotel rooms can be hard to come by. 

If you are arriving by car from Miami, and are on a budget, you can stay at a lower cost, probably older, hotel a few islands north -perhaps as far north as Marathon- or Key Colony area for instance.  If you do this, check in at your hotel first, then drive down to Key West by mid-afternoon to ensure you get a parking space. There is pay parking at public parking lots -at a steep price for the event ($20-25 is a fair estimate in close walking distance to Duval St and Mallory Sq area).

No matter what day of the week you arrive in Key West, you will have the chance to experience at least one fete: the Sunset Celebration. Every evening two hours before sunset, artists, psychics, food vendors, performers and thousands of conchs (locals) and tourists flock to Mallory Square and to shop, socialize and watch for the colorful and often dramatic end to another day.

You can also visit Key West's Official website for an up-to-date list of the events and festivals happening in Key West. 

We really enjoyed a more low key festival called the song writers festival (last week april/first week May).  Great music with great lyrics  all over town!!