Our Privacy Policy

Events in the Florida Keys

Event calendar provided with the courtesy of the Monroe County Tourist Development Council.

Events in Florida Keys for 2021

  • September 24 - September 26 Marathon
  • Marathon International Bonefish Tournament
  • Barb Hewlett 305-304-8682 Email Website
  • Staged for over 60 years, this mid-Keys tournament is one of the Keys' oldest. Registration and Captain's meeting kick off the event. Anglers traditionally fish 8:30 a.m. to 3:30 p.m. Friday - Sunday. Fish check-in, socially-distanced cocktail parties and awards ceremony to be held at a TBD location.

  • September 24 - September 26 Key Largo
  • Take Stock in Children Backcountry Challenge
  • Website
  • This annual tournament offers anglers the opportunity to win coveted trophies for trout, snook and redfish. A popular weekend auction showcase and Sunday evening dinner are open to the public. Proceeds support local vocational scholarships for all ages and Take Stock in Children scholarships for financially challenged Upper Keys students.

  • October 02 - October 02 Key West
  • 24th Annual Key West Paddle Classic
  • Sue Cooper 305-304-4259 Email Website
  • Watersports enthusiasts on paddleboards and other self-propelled watercraft can race around the continental United States’ southernmost island during the annual Key West Paddle Classic. Presented by Lazy Dog Adventures, the 12-mile challenge takes competitors past island landmarks such as the Southernmost Point marker, Fort Zachary Taylor Historic State Park and Mallory Square, site of Key West’s nightly sunset celebration.

  • October 07 - October 28 Key West
  • Smallest Parade in the Universe
  • Website
  • Everyone’s favorite miniature parade returns! Artists compete for cash prizes and bragging rights with pint-sized floats to suit this year’s Fantasy Fest theme: All-A Daze for a Holiday! The fantastical entries are on view all month before being auctioned Oct 23 at 7 p.m., at The Studios of Key West, and 533 Eaton St., with proceeds to benefit MARC House.

  • October 09 - October 10 Islamorada
  • Sixth Annual Oktoberfest
  • Website
  • German beers on draft and locally brewed German-style beers on draft! Attendees can enjoy food trucks, live traditional German food and music both days; art vendors; face painting, games; traditional Das Boot competition. Visit event link for daily hours and details.

  • October 10 - October 10 Key West
  • Justin Hayward, Nights Tour
  • Website
  • The voice of Moody Blues joins Mike Dawes for a night of music at Key West Theater, 512 Eaton St. Doors open 7 p.m.; show starts 8 p.m.

  • October 11 - October 13 Islamorada
  • Islamorada All-Tackle Bonefish and Permit Championship
  • Email Website
  • Dubbed the “Fall All-Tackle,” the three-day challenge attracts energized newcomers to face seasoned veterans in a competition that has taken place since 1970. One angler per boat pairs with a licensed captain to vie for division winners’ trophies for the three longest bonefish and three longest permit. The field is limited to 25 participants.

  • October 14 - October 17 Key Largo
  • Reef Fest 2021: An Annual Celebration of Marine Conservation
  • Email Website
  • REEF Fest includes diving, snorkeling, kayak eco-tours, ocean-themed seminars, and social events. Since 2015, REEF has hosted REEF Fest each fall in the Florida Keys. Divers, snorkelers, and ocean lovers attend REEF Fest to celebrate their love of marine life and learn about the latest in conservation. Weekend schedule is to include REEF Marine Conservation Programs, dive, snorkel and kayak trips, seminars with renowned ocean experts and more.

  • October 15 - October 17 Islamorada
  • “Ladies, Let’s Go Fishing!” Florida Keys Saltwater Seminar
  • Website
  • Female fishing fans can learn or polish angling skills during the award-winning weekend seminar. More than 8,000 female graduates have immersed themselves in the lighthearted yet skill-heavy curriculum to learn and hone abilities in offshore, bottom, inshore and fly fishing. Participants can network on Friday, learn on Saturday and go fishing on Sunday. Sign up for Friday fishing to be entered into the Fishing Fever’s non-intimidating competition for those fishing both days.

  • October 22 - October 31 Key West
  • Key West Fantasy Fest
  • Website
  • This outrageous 10-day costuming and masking celebration features dozens of masquerade competitions, themed parties and other exuberant events. The 2021 theme is 'All a Daze for a Holiday!' Check the website for the full schedule and more details.

  • October 23 - October 23 Marathon
  • Stone Crab Claw Eating Contest
  • Website
  • In this unique contest, amateur eaters age 18 and over compete to crack and consume 25 stone crab claws, picking them clean, in the fastest time. If a tie occurs, a 10-claw tiebreaker will be held to determine the winner. The much-anticipated event is to be staged at Keys Fisheries Market and Marina, located off U.S. Highway 1 on Marathon’s 35th Street gulfside. Stone crab season runs from Oct. 15 to May 15 each year. The Keys are a top supplier of the succulent delicacy to restaurants throughout the United States.

  • October 26 - October 26 Key West
  • Key West Burlesque presents: Harry Potter and the Enchanted Tassle, A Parody
  • Website
  • Ready your wands and study your spells! It's time to enter the wizarding world of Harriet Potter and the Enchanted Tassel: A Burlesque Parody. Whether you're Gryffindor, Ravenclaw, Hufflepuff, or Slytherin, this enthralling show is sure to have you on the edge of your Nimbus 2000 as you join Auntie Harriet Potter on a salacious search for a magical missing tassel. Doors open 7PM, show starts 8PM at Key West Theater, 512 Eaton St.

  • October 29 - October 30 Islamorada
  • Fall Backcountry Fly Championship Series
  • Website
  • Tournament anglers are to compete to catch the most inches of snook and redfish on fly in a challenge where 1 inch equals 1 point. Awards are to be given to the grand champion, the anglers who catch the largest snook and redfish and the “King of the Backcountry” series grand champion, among others.

  • October 31 - November 06 Islamorada
  • BubbaFest Florida Keys
  • Website
  • Adventure fans can experience the Florida Keys’ subtropical breezes and panoramic open-water views from the seat of a bicycle during the 200-mile BubbaFest Bike Tour set for Oct. 31 through Nov. 6. Participants ride throughout the Keys island chain, with ample free time for exploration and enjoyment. Resort accommodations, many meals and plenty of sunshine, scenery and memories are included. 

  • November 03 - November 03 Key West
  • The Studios of Key West presents: The Mon Valley Medium
  • Website
  • Alec Silberblatt’s one-person play tells the story of Mack, a yinzer (meaning he grew up and lives in the Mon Valley of Western PA) who always believed in ghosts. But after the local medium proves himself to be a fraud, Mack is left questioning what is true and what is perception. In his darkly comic tale, Silberblatt takes the audience through one man’s involvement in a vigilante killing, and into an investigation of why we believe what we believe. Held in the The Studios of Key West Courtyard at 529 Eaton St. Show starts 6:30 p.m. Tickets available online. Seating is limited.

  • November 04 - November 06 Big Pine Key
  • Eighth Annual LKGA Sugarloaf Showdown
  • Email Website
  • Presented by the Lower Keys Guides Association, the tournament raises money for the Florida Keys Guides Trust Foundation. The foundation provides funds to assist fishing guides who are recovering from an illness or injury. Participants must use either spin or fly tackle to pursue the catch-and-release tournament’s target species of bonefish, permit and barracuda. A maximum of three fish of each species can be scored per team per day.


  • November 07 - November 14 Key West
  • Race World Offshore World Championship
  • Website
  • Racing teams and fans are to gather in Key West for an amazing Offshore World Championship experience. RWO is the premier Offshore Racing Sanctioning body in the United States and is dedicated to producing an unforgettable week. With the most experienced team in all of offshore racing around the world, RWO anticipates another spectacular event.

  • November 07 - November 07 Key West
  • Mike Nash & Southern Drawl Band
  • Website
  • With story teller songs about life and love, lyrical tales from the unique people he's met along the way, and of course plenty of summertime "drinkin' at the lake tunes" with an island-inspired twist, there's something in a Mike Nash show for everyone to relate to. Doors open 6 p.m.; show starts 7 p.m. at Key West Theater, 512 Eaton St.

  • November 09 - November 11 Key West
  • Bum Farto: The Musical
  • Website
  • Based on a true and crazy Key West story, this show features an exceptional cast of 18 singers, dancers and actors performing 14 song and dance numbers in styles ranging from salsa to Carolina Shag and even includes a tap dancing ‘Square Fish’!  Show starts 8 p.m. at Key West Theater, 512 Eaton St.

  • November 12 - November 14 Islamorada
  • Cheeca Lodge & Spa All-American Backcountry Tournament
  • Website
  • Anglers compete for prizes and trophies in this annual event targeting snook, redfish, bonefish, tarpon and permit. The tournament was inspired by the 41st U.S. President George H. W. Bush and honors war heroes in the esteemed competition held over Veteran’s Day weekend. Proceeds benefit the Guides Trust Foundation.

  • November 13 - November 13 Islamorada
  • ‘A Havana Night at the Museum’ at Florida Keys History & Discovery Center
  • Website
  • For one night only, guests are to gather in the open air to visit 1940s Havana in its heyday as “America’s Playground” where tropical breezes flow and cabaret music excites. Gather your friends to hit the casino tables, enjoy a game of dominoes and toast with a specialty cocktail. Guests will enjoy a cocktail reception, an elegant dinner with dessert, as well as opportunities to bid on trips, jewelry, personal indulgences and more, in the live and online auctions – all while experiencing “the Wonder-land of America!” The fifth annual signature fundraising event starts at 6 p.m. outside on the Islander Resort Conference Center’s Tarpon Terrace, MM 82.

  • November 14 - November 14 Key West
  • Montessori United 5k & Kids' Fun Run
  • Website
  • Walk, run or stroll this 5K/1m/.5m to support Montessori education in Key West! Finisher medals given to all participants, t-shirts to the first 150 to register. Award medals for the 5K and 1mile races! Starts at 8 a.m., Higgs Beach. Register online. Proceeds benefit May Sands Montessori School & the Montessori Children's School.

  • November 14 - November 14 Key Largo
  • First State Bank Key Largo Bridge Run
  • Website
  • Runners from around the U.S. and other countries can challenge their best times amid spectacular scenery during this Half Marathon & 4-Mile Run/Walk event over the beautiful Jewfish Creek Bridge at the top of the Florida Keys Overseas Highway, overlooking the Key Largo Bay. Race finishes at Rowell's Waterfront Park. The course is USATF certified.

  • November 17 - November 21 Key West
  • Key West Film Festival
  • Website
  • Showcasing films that exhibit excellence in storytelling, the festival's lineup is to feature special events, as well as screenings at Tropic Cinema, 416 Eaton St. The four-day program is to include several films from multiple genres and categories as well as social events with filmmakers, actors and film lovers. KWFF strives to showcase the best of Florida filmmaking talent, while highlighting visiting filmmakers and industry leaders through discussions and workshops, with access to some of the biggest names in the film business. The festival also looks to support the next generation of local student filmmakers with scholarships and other key awards.

  • November 19 - November 20 Key West
  • The SMART Ride 18, Pedal to Paradise
  • Website
  • The SMART Ride is a 2-Day, 165 mile bicycle ride from Miami to Key West every November. SMART Ride is the second largest AIDS bicycle ride in the country and the only one of its size to give back 100 percent, totaling $12.4 Million to AIDS Service Organizations since 2003. Register online to join.

Back to the top