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The fall season in the Florida Keys & Key West is known for warm weather, sunny skies and an array of events to entertain. From pillaging pirates to high-speed powerboats to eco-conscious happenings, the Florida Keys & Key West has an event to interest virtually everyone.

While this piece lists selected fall 2012 highlights, a comprehensive schedule of events throughout the Keys can be found at

Sept. 20-22: Conched In Key West Charity Bar Crawl. Key West. A group of island inspired business owners got together for what was just going to be a trip to Key West, but turned into a bar crawl with a good cause. The 2nd annual Conched in Key West charity bar crawl takes place on Saturday September 22nd, but their will be pre-party on the Key West Express ferry boat Thursday the 20th. Visit the bar crawl Facebook page for more information.

Oct. 4-7 & Nov. 8-11: Coral Restoration Workshop. Key Largo. Participants can become citizen scientists in a hands-on program that teaches the importance of coral health and corals’ function in marine ecosystems. Scuba-certified participants go on a working dive at the coral nursery, an orientation dive at some of the completed restoration projects and two dives to plant corals on a new restoration site. Visit or 305-451-3595.

Oct. 18-21: Key Largo Pirates Festival. Key Largo. Buccaneers and wenches can enjoy piratical fun including a costume contest, walk the plank event, rum tasting, booty hunt, pirate show, thieves market, underwater poker and more. Visit or call 305-394-3736.

Oct. 18, Nov. 15, Dec. 20: Morada Way Arts & Cultural District presents: Third Thursday Art Walk. Islamorada. Showcasing the fine arts, music and culinary nuances of the Purple Isles, this free cultural celebration features national and local artisans who are showcased in galleries at Morada Way between mile markers (MM) 81 and 82 — as well as “culinary art” and live music from 6-10 p.m. In addition to individual artists, participants include the Redbone Gallery, Gallery Morada, Pasta Pantaleo Signature Gallery, Bluewater Potters and more. Visit or call 305-664-9100.

Oct. 19-20: Goombay Festival. Key West. Held in Key West’s historic Bahama Village neighborhood, the lively Goombay is known for its island-style food, arts and crafts, nonstop live entertainment and dancing in the streets. Visit for more information.

Oct. 19–28: 33rd Annual Fantasy Fest. Key West. This outrageous 10-day costuming and masking celebration features flamboyant costume competitions including one for pets, promenades, street fairs and a grand parade that stars marching groups, island bands and lavish floats. Visit or call 305-296-1817.

Oct. 20: Underwater Pumpkin Carving. Key Largo. Divers become underwater artists as they turn pumpkins into Halloween masterpieces beneath the sea in the Florida Keys National Marine Sanctuary. Visit or call 305-451-3595.

Nov. 4-11: Key West World Championship Powerboat Races. Key West. High-speed powerboats continue Key West’s longstanding tradition in a challenge described as the Indianapolis 500 of powerboat racing. Visit or call 305-296-6166.

Nov. 10: Key Largo Bridge Run. Key Largo. Enjoy the sunrise where the Atlantic Ocean meets the Gulf of Mexico during the morning race over part of the historic 18-Mile Stretch and the Jewfish Creek Bridge at Key Largo, gateway to the Keys. The race is an outreach of Key Largo Baptist Church. Visit for more information.

Nov. 21 – Dec. 31: Key West “Bight” Before Christmas Holiday Celebration. Key West. The harbor walk along the Historic Seaport at the Key West Bight, stretching from Greene Street to Grinnell Street, is to be festively lit from rooftops to the sea for the holiday season. Celebrate with holiday events, browse at unique island shops and galleries, and relax at waterfront restaurants and watering holes. The festivities are presented by the Key West Bight Preservation Association. Visit or call 305-304-2633.

Nov. 24: Big Pine & the Lower Keys Island Art Festival. Big Pine Key and the Lower Keys. Highlights of this holiday event include live music by local entertainers, food, exhibits and booths featuring locally produced arts and crafts. Festivities traditionally take place on the grounds of the Lower Keys Chamber of Commerce, MM 31 oceanside. Visit or call 305-872-2411.

Nov. 29 – Dec. 2: Key West Film Fest. Key West. Showcasing films that exhibit excellence in storytelling, the festival’s lineup is to feature screenings and special events hosted at landmark venues throughout Key West, including the Tropic Cinema and San Carlos Institute. The four-day program is to include 25 films from multiple genres and categories as well as social events. Visit or call 941-527-9385.

Nov. 30 – Dec. 2: Christmas in the Keys. Marathon. Full of food, beverage, vendors, music and entertainment for the entire family, this Middle Keys celebration kicks off the holiday season. The three-day event is to be headquartered at Hawks Cay Resort, located on Duck Key. Call 305-289-4901.

Nov. 30 – Dec. 2. ART! KEY WEST! Key West. A vibrant three-day festival and art walk are to celebrate all the arts in Key West. The schedule includes visual, performing, literary, film and musical events, performances and exhibitions. Galleries are to have extended hours and exhibitions, and art and culinary pairings are to be offered at local restaurants. E-mail [email protected].

Dec. 7: Florida Keys Holiday Festival. Islamorada. This extravaganza traditionally begins with a tree-lighting ceremony at Founders Park, MM 87. Other attractions typically include a holiday parade featuring Santa, a 20-ton mountain of snow for mitten-clad munchkins, a holiday gift bazaar and a silent auction of ornaments decorated by local artists. Visit or call 305-664-4503.

Dec. 8 and 15: Lighted Boat Parades. Key Largo, Middle Keys, Lower Keys and Key West. Decorated and lighted boats are to cruise through Keys waters Dec. 8 at Key Largo’s Blackwater Sound and Marathon’s Boot Key Harbor, and Dec. 15 in Key West Harbor and the Lower Keys’ Pine Channel Causeway. For the Key Largo Holiday Boat Parade visit or call 305-451-4502; for the Key West Lighted Boat Parade visit or call 305-292-3302; for the Boot Key Harbor Lighted Boat Parade visit and for the Lower Keys Lighted Holiday Boat Parade call 305-923-5370.

Dec. 31: New Year’s Eve Fireworks on Blackwater Sound. Key Largo. The back bay is the setting for the annual New Year’s Eve fireworks extravaganza hosted by Sundowners, Señor Frijoles, Cactus Jack’s, Gus’ Grille at the Marriott Key Largo Beach Resort and the Caribbean Club, MM 103-104. Visit or call 305-451-4502.

Dec. 31: Key West New Year’s Eve Celebrations. Key West. The Southernmost City celebrates with a “conch shell drop” at Sloppy Joe’s Bar, 201 Duval St.; the descent of a super-sized red high-heel shoe carrying drag queen Sushi at the Bourbon St. Pub/New Orleans House complex, 724 Duval St., and the descent of a pirate wench from atop a tall ship’s mast in the island city’s Historic Seaport. Call 305-296-2388, 305-293-9800 and 305-292-3302, respectively.

Florida Keys visitor information: or 1-800-FLA-KEYS (1-800-352-5397)
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(Lead photo from © Monroe County Tourist Development Council)


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