Key West Fall Festival Guide



5 Reasons Why You Should Visit Key West in the Fall

2016 Key West Fall Festival Guide

Goombay Festival Oct. 19, 20

Goombay is a two-day family friendly celebration that spotlights Key West’s Bahamian Heritage showcasing island arts, crafts, music and food in the heart of Key West’s historic Bahama Village.   In addition to the food, music and vendors, one of the highlights taking place each night is when The Junkanoos, costumed marchers, parade through Petronia Street.  It’s a parade, it’s dancing in the streets, it’s a celebration…it’s Goombay!  Insider Tip: This is a local’s favorite event!

Fantasy Fest October 21 – 30

Key West celebrates Fantasy Fest each year at the end of October with a 10-day festival where fun-loving revelers from around the world bring their creativity, costumes and imagination to the southernmost city!  It’s outrageous… it’s fun…it’s creative…it’s Fantasy Fest!  Be prepared to bring more than one costume and enjoy the festivities throughout the week:  Costume contests, parties and flamboyant masquerade competitions – even one for the pets, street fairs, the Locals Parade (Masquerade March) a grand parade with marching groups, lavish floats and bands.  The 2016 festival theme is “Political Voodoo & Ballot Box Barbarians.” Visit the Fantasy Fest website for the 2016 Fantasy Fest schedule of events and read our Ten Tips and Must Do’s for festival attendees.


25th Annual Meeting of the Minds “Parrot Heads in Paradise” Nov. 2 – 6


Photo by Rob O’Neal, Florida Keys News Bureau

Each year, more than 3000 Jimmy Buffett fans head to Key West for the Parrot Heads in Paradise, Meeting of the Minds convention.  This is a private convention where most activities are only open to registered members.  However, one of our favorite events during the Meeting of the Minds is the concert and street festival on Friday that is open to the public: The Lone Palm Foundation Meeting of the Minds Street Festival: Steve Hopper and the Wolf Island Band, Phin Addicts Band, Johnny Russler & the Beach Bums Band, will be performing Friday, November 4th – 1PM – 6:30PM Corner of Duval and Fleming Streets.

Surprise, Surprise!  Did you know Jimmy Buffett surprised the Parrot Head fans during the Meeting of the Minds convention in November 2011?  Watch the video – Jimmy Buffett plays surprise Key West Concert.  If you are visiting Key West during the Meeting of the Minds, enjoy paradise with the parrot heads and you never know who might show up!

Parrot Heads In Paradise.


36th Annual Key West World Championship Races Nov 6 – 13


Photo Credit: Super Boat International

Super Boat International returns to Key West in November for the 36th Annual Key West World Championship Races, internationally known as the Indianapolis 500 of the offshore powerboat racing.  If you like fast boats, you won’t want to miss this event.

Race day is exhilarating!  Helicopters fly above the 6.5-mile course as high-speed offshore powerboats race in Key West Harbor for the 2016 world championship title.  There is thunder, rumble and roar…its fast boats, fun, excitement and another one of our fall favorites in paradise.  If you are interested in purchasing VIP tickets or watching the races by boat make sure visit the Concierge when you arrive.

This week long event kicks off on Sunday, November 6th as Race Village opens and at 4pm there is a Boat Parade on Duval Street.

Race Days:

Wednesday, November 9, 2016 – Race Day #1

Friday, November 11, 2016 – Race Day #2

Sunday, November 13, 2016 – Race Day #3

To view the complete schedule of events for the 36th Annual Key West World Championship Races visit


Key West Film Festival, November 16 – 20


The 2016 dates for the Key West Film Festival have just been announced and they are November 16 – 20.

This four-day event will showcase films that exhibit excellence in storytelling.  There will be screening and special events throughout the island and a four-day program that includes films from multiple genres and categories, and social events with filmmakers, actors and film lovers.  This event is one to watch, as the detailed schedule of events will be announced shortly.  Watch the 2016 Key West Film Festival Trailer and visit the Key West Film Festival website to learn more.


As you can see there is a lot going on during the Fall in Key West and above we’ve highlighted just a few of our favorites. Do you have a favorite Key West Festival, Event, Celebration you want to see highlighted?  Let us know and we’ll make sure to cover it for you.


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