Second half of 2019 has plenty of celebratory events in Key West

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The second six months of each year in the Florida Keys & Key West are always festive, with lively and offbeat events throughout the 125-mile-long island chain. There are always only-in-the Keys activities for visitors eager to enjoy marine life and the unique environment, fresh dock-to-dish seafood and luscious cuisine and the engagingly laid-back atmosphere of the Keys.
Here are highlights of some major events from July through December including the 40th anniversary of the zany and colorful 10-day Fantasy Fest in late October. A more detailed schedule of Keys events can be found at
The Key Lime Festival (July 4-7), now in its seventh year in Key West, salutes the tiny, tangy fruit that inspired Key lime pie, the Florida Keys’ signature dessert. The festival schedule includes a Key lime pie eating contest, Key Lime Cocktail Sip & Stroll, a Key Lime Pie Hop tasting tour and a gravity defying “pie drop” from atop the Key West Lighthouse.
Key West Mermaid Festival (July 5-7), the first of its kind in the Keys, is to showcase awareness of oceans and salty shores. Events include mermaid meet-ups, sunset celebrations, mojitos with mermaids and a Salty Street Fair.
The 35th Annual Underwater Music Festival (July 13), a nationally acclaimed submerged songfest in the Lower Keys, is held at Looe Key Reef in the Florida Keys National Marine Sanctuary to promote reef preservation. Divers and snorkelers can explore part of the continental United States’ only living coral barrier reef while rocking to a unique sub-sea concert.
Hemingway Days (July 16-21) held in Key West, celebrates the life and work of legendary author Ernest Hemingway, who lived and wrote on the island during the 1930s. Highlights include the Hemingway Look-Alike Contest for stocky bearded men, prose and poetry readings, the wacky “Running of the Bulls,” presentations on the writer’s influence and a three-day marlin tournament recalling his passion for deep-sea angling.
Key West BrewFest (Aug. 29 to Sept 2) is a Labor Day weekend event now in its 10th thirst-quenching year. It’s highlighted by an Aug. 31 signature tasting event with nearly 200 beers and microbrews on tap. The festivities benefit the Key West Sunrise Rotary Club of the Conch Republic.
Womenfest (Sept. 4-8) brings thousands of women from across the globe to Key West for one of North America’s largest gatherings of lesbians and their friends. Events created by the Key West Business Guild typically include active adventures, flag football, pool parties and live performances.
Bahama Village Goombay Festival (Oct. 18-19), a lively family-friendly event in Key West’s historic Bahama Village neighborhood, celebrates island-style food, arts and crafts, live entertainment and dancing in the streets. It’s held noon to midnight both days on the first weekend of Fantasy Fest.
Fantasy Fest (Oct. 18-27) marks four decades of masquerade madness with a 10-day extravaganza themed “In Tune but Off Key: Celebrating 40 Years of Fantasy!” The outrageous costuming and masking festival is recognized around the world. Highlights include a costume competition for pets, a headdress ball, themed parties, street fairs, a madcap march and a lavish parade with dazzling large-scale floats, walking groups and island-style bands.
The Key West World Championship Race (Nov. 3-10), sometimes called the Indianapolis 500 of powerboat racing, features high-speed offshore powerboats and adrenaline-fueled action. Part of the course runs through Key West Harbor, offering smooth water where racers can achieve speeds above 140 mph and provide fans breathtaking displays of skill and power.
The Stone Crab Claw Eating Contest (Nov. 9), presented by Keys Fisheries in Marathon, celebrates the much-anticipated opening of Florida’s stone crab season that takes place Oct. 15 each year. In the wacky contest, participants age 18 and older vie to crack and cleanly consume 25 stone crab claws in the shortest time.
The Key West Film Festival (Nov. 20-24) themed “passion meets paradise,” typically features screenings and special events at landmark venues throughout Key West. The fest showcases films that illustrate creativity, diversity, sustainability and beauty — elements capturing the heart of Key West, the United States’ southernmost island city.
The Big Pine & The Lower Keys Island Art Festival (Nov. 30) features locally produced arts and crafts, live music and food. Attendees can show their holiday spirit and choose unique artisanal gifts for friends and family at the annual open-air fair, traditionally held in Big Pine on the grounds of the Lower Keys Chamber of Commerce.
Key West Holiday Fest (Dec. 1-31) spotlights a wide range of seasonal celebrations including the illumination of the Harbor Walk of Lights, a hometown holiday parade, tours of decorated historic inns, a lighted boat parade and lively New Year’s Eve celebrations.
The I Love Stock Island Festival (Dec.13-15), on the Lower Keys island renowned for its rustic and authentic working waterfront, is a family-friendly blend of music, food, history and art studio tours, watersports and fresh-off-the-boat seafood celebrations.
New Year’s Eve “Drops” in Key West Ring in 2020 with a “conch shell drop” at Sloppy Joe’s Bar; the descent of a super-sized red high-heel shoe carrying drag queen Sushi at the Bourbon St. Pub/New Orleans House complex; the lowering of a pirate wench from atop a tall ship’s mast at the Schooner Wharf Bar; and a huge replica Key lime wedge splashing down into a larger-than-life margarita glass at Ocean Key Resort & Spa.


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