Six Crazy-Great Fall Festivals In The Florida Keys

October 1, 2009 | By | Reply More
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Few places on earth can match the free spirit revelry that is ready to party-out anytime, anyplace as in the Florida Keys. Each fall as summer temperatures cool, party temperatures rise with a host of funky, fun fall festivals. Here’s a list of 6 wild and crazy events that you have to experience to believe:

Casting For Cats – An All Female Fishing Tournament, October 17-18, 2009
About half way down the chain of keys you’ll find the once sleepy fishing community of Islamorada (say I’ll a more adda). This has been the fishing capital of the keys since long before Ernest Hemingway put it on the in-crowd map. In mid-October all ladies are invited to cast their lines in a Women’s Backcountry Fishing Tournament for the benefit of Caring For Cats, a local non-profit pet rescue organization.

Key Largo Pirates Fest – Outrageous Fun Above and Below the Water – October 22-25, 2009
Release your inner-pirate where buccaneers roamed and sea captains plundered and pillaged. The festivities begin with a Captain Morgan look-alike plunder party, followed the next day by Black Caesar’s Pirates Parade and the party continues for days.

The Goombay Festival – An Exuberant Bahamian Street Festival – October 23-24, 2009
Bahamians have been crossing back and forth between the Bahamas and the Keys since the early 1800’s. Today Key West boasts a robust Bahamain community that celebrates their heritage each fall with a family friendly celebration of dancing in the streets, Caribbean cuisine, Bahamian crafts, costumed stilt walkers and a grand parade that kicks off Fantasy Fest.

Fantasy Fest – Words Fail Me And Yours Will Too! – October 23-November 1, 2009
The most outrageous, pushing the limits, gala street festival imaginable. Your eyes will pop and your mouth will gape – everyone has a blast and you will never forget that you’ve been there. (Caution – this event is not intended for family audiences.)

Under Water Pumpkin Carving Contest – October 25, 2009
Super imaginative pumpkin carving contest 30 feet under the ocean in scuba gear sponsored by Amoray Dive Resort in Key Largo.

BubbaFest Bike Tour – A Glorious Scenic Ride From Key Largo to Key West – November 7-14, 2009
When freezing temperatures have forced you to put your bike in the basement up north, the weather is perfect for a long leisurely scenic bike ride in the Florida Keys. The BubbaFest welcomes riders of all abilities for a week long journey through all the keys and back again. Riders enjoy resort camping, lots of time for water sports, amazing aqua views and mostly flat terrain.

Surely there is something in the Florida Keys you’ll love this fall! Check out special festival hotel rates (some up to 50% off) at


Parrot Heads In Paradise – Jimmy Buffet 18th annual Meeting of the Minds takes place in Key West from November 5-8, 2009.  The annual Parrot Head convention is a menagerie of beach parties, concerts, and charity events.

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Category: Family Vacations, Florida Travel Tips, Unique Vacations