This calendar highlights 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 fla-keys.com/calendar.
The Key Lime Festival (July 4-7; keylimefestival.com), 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; keywestmermaidfestival.com), 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; lowerkeyschamber.com), 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; hemingwaydays.net), 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.
The Hemingway 5k Sunset Run/Walk & Paddleboard Race (July 20; keywesthalfmarathon.com) take place in Key West as part of the annual Hemingway Days events and recall the legendary author’s vigorous sporting lifestyle. Paddlers compete on an ocean course, while runners and walkers proceed through Key West’s colorful historic district past landmarks that include the Ernest Hemingway Home & Museum.
Tropical Heat (Aug. 14-18; tropicalheatkw.com) is an all-male celebration presented by Key West Business Guild, with planned events including pool and dance parties, on-the-water adventures and a fashion show to raise money for a local nonprofit.
Key West BrewFest (Aug. 29 to Sept 2; keywestbrewfest.com) 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.
Heroes Salute Weekend (Aug. 30 to Sept. 1; hawkscay.com/about-hawks-cay-resort/heroes-salute) is a Middle Keys tradition at family-friendly Hawks Cay Resort on Duck Key honoring military, fire and rescue, law enforcement and medical personnel. Three days of patriotic All-American activities include a barbecue, athletic events, a live music concert and fireworks.
Womenfest (Sept. 4-8; womenfest.com) 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.
The Florida Keys Poker Paddle (Sept. 6-8; paddleguru.com/races/FloridaKeysPokerPaddle2019) supports military service personnel with a “poker” paddle race for kayaks and stand-up paddleboards in Islamorada. A 4-mile main event Sept. 7 features five stops in mainly shallow water including two sandbars. A Friday packet pickup party and an awards party round out the schedule.
Reef Environmental Education Foundation’s 10th Annual Upper Keys Lionfish Derby & Festival & 2019 Series Finale (Sept. 13-15; reef.org/reefs-2019-lionfish-derby-and-festival-series), themed “Let’s Take a Bite Out of Lionfish,” is to be staged at Founders Park in Islamorada. Participants can catch and collect invasive lionfish from area waters and learn how to score, fillet and dissect the predator fish. Educational seminars and eco-adventures with prestigious leaders in diving and marine conservation are featured. Prizes are to be awarded to lionfish series champions.
The Swim for Alligator Lighthouse (Sept. 14; swimalligatorlight.com) is Islamorada’s 8-mile open-water swimming competition for solo entrants and two-, three- and four-person relay teams. Distance swimmers can test their endurance as they race to the landmark lighthouse and back, helping raise awareness about the need to protect historic lighthouses on Florida’s coastal waterways.
The Conch Scramble Charity Golf Tournament (Sept. 27-28; conchscramble.com), a popular Islamorada “par-tee” on the water, features floating greens, golf boats and biodegradable fish food golf balls. Fans of golf and boating can expect to have a “hole” lot of fun honing their swings and raising money for charity one shot at a time. Teams make stops at multiple waterfront venues and come ashore to tee off, aiming for floating holes.
The Southernmost (SoMo) Marathon & Half Marathon (Oct.12; somomarathon.com) includes 26.2-, 13.1- and 3.1-mile challenges featuring Atlantic Ocean and Gulf of Mexico views and iconic Key West landmarks. All participants get a T-shirt, while medals await all finishers and awards are presented following the racing action.
REEF Fest (Oct. 17-20; reef.org/REEFFest), held in Key Largo and hosted by the Reef Environmental Education Foundation, celebrates the impact and success of marine conservation initiatives in the Keys. Attractions include educational seminars, social gatherings, diving and eco-adventures with prestigious leaders in diving and marine conservation. All REEF Fest events are open to the public, but pre-registration is requested. Seminars at the Murray Nelson Government Center are free.
Bahama Village Goombay Festival (Oct. 18-19; fantasyfest.com), 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; fantasyfest.com) 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; superboat.com), 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 First State Bank Key Largo Bridge Run (Nov. 9; runsignup.com/Race/FL/KeyLargo/KeyLargoBridgeRun) offers runners the opportunity to greet the sunrise where the Atlantic Ocean meets the Gulf of Mexico. The challenge features 5k run/walk and 10k run races traversing the Jewfish Creek Bridge.
The Stone Crab Claw Eating Contest (Nov. 9; keysfisheries.com), 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.
Taste of the Islands (Nov. 10; facebook.com/BPWMarathonTaste/) at Marathon Community Park showcases culinary treats and includes a new smoked fish dip amateur competition. The event is sponsored by the Marathon chapter of Business & Professional Women and proceeds from ticket sales benefit local scholarships. Admission is free.
The SMART Ride (Nov. 14-16; thesmartride.org) includes a full century ride, “Pedal to Paradise,” from Coral Gables to Hawks Cay Resort on Duck Key on Friday with pit stop snacks, dinner and an overnight stay. Saturday features a 65-mile ride to Key West with stops every 15 to 20 miles. Celebratory parties include festivities at Duval Street venues. On Sunday, participants can take a Sunset Fury Cruise. TSR Adventures Inc. hosts the event, which raises funds for Florida agencies that benefit those affected by HIV/AIDS.
The Old Island Restoration Foundation’s 60th Anniversary Celebration (Nov. 15, 2019, to March 31, 2020; oirf.org) begins in Key West with a Nov. 15 party at the Oldest House Museum and Gardens showcasing a “60 Years of Home Tour Posters” exhibit. The foundation’s annual tours, celebrating significant Key West houses and gardens, are among America’s longest running. As well as four weekends of home tours, the anniversary celebration includes a speaker series, social events and the foundation’s famed annual Conch Shell Blowing Contest.
The Key West Film Festival (Nov. 20-24; kwfilmfest.com), 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; lowerkeyschamber.com) 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; keywestholidayfest.com) 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 Islamorada Chamber of Commerce Florida Keys Holiday Festival (Dec. 6; islamoradachamber.com) is a magical seasonal gathering — complete with a 30-ton snow mountain, holiday parade, community tree lighting and visit from Santa at Founders Park beach, mile marker 87 bayside.
Key West Triathlon (TRIKW) Sprint & Olympic Triathlon (Dec. 6-7; trikw.com) challenges participants to swim in the waters of the Atlantic Ocean, bike along a portion of the Florida Keys’ scenic Overseas Highway and run on a fast, flat course beside the Atlantic. As well as the Olympic-distance and sprint-distance triathlons, Aquabike, Aquathlon and sprint duathlon competitions are featured.
Islamorada Half Marathon and 10k (Dec. 8; islamoradahalfmarathon.com) celebrates its fifth annual event at Robbie’s in Islamorada, mile marker 77.5 bayside. The associated fun-while-you-run Beach N’ Beer Mile kicks off at noon.
The I Love Stock Island Festival (Dec.13-15; ilovestockisland.org), 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 Fireworks on Blackwater Sound (Dec. 31; keylargofireworks.com), hosted by Key Largo restaurants and resorts near mile marker 104, features a back bay setting for a popular Upper Keys fireworks extravaganza.
New Year's Eve “Drops” in Key West (Dec. 31; sloppyjoes.com, bourbonstpub.com, schoonerwharf.com, facebook.com/SunsetPierKeyWest/, firstflightkw.com and smokintunasaloon.com) ring in 2020 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.; the lowering of a pirate wench from atop a tall ship’s mast at the Schooner Wharf Bar, 202 William St., and a huge replica Key lime wedge splashing down into a larger-than-life margarita glass at Ocean Key Resort & Spa. Revelers also flock to First Flight Island Restaurant & Brewery, 301 Whitehead St., for the midnight landing of a replica aircraft carrying a flight attendant at a historic building that housed Pan American Airways’ first ticket office. Smokin’ Tuna Saloon, 4 Charles St., features an offbeat “tuna drop.”
Florida Keys calendar of events: fla-keys.com/calendar
Florida Keys visitor information: fla-keys.com or 1-800-FLA-KEYS
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