Events in the Florida Keys

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

Events in Florida Keys for 2022

  • August 10 - August 14 Key West
  • Key West Tropical Heat
  • Website
  • Enjoy five days of sizzling happenings in the island city whose openness and respect for diversity have made it a world-renowned gay vacation destination. The festival’s intriguing events range from all-male theme parties, pool parties, clothing-optional events and adult-oriented entertainment showcase the island’s LGBTQ venues. Attendees can also enjoy activities ranging from eco-tours to museum explorations.

  • August 10 - August 10 Islamorada
  • The Matecumbe Historical Trust presents “A Taste of History Dining Event”
  • Barbara at 305-393-0940
  • Learn about the history between Upper and Lower Matecumbe Keys, an area known as the Fill. The Fill has an interesting and storied past. Through an audio-visual presentation you will learn when Henry Flagler filled in the area for the railway, the building of the bridges, buildings that were on the fill, concrete picnic tables and more. The dining venue is the Chart Room at Old Conch Harbor located at 90311 Old Highway, Tavernier. Dinner includes filet mignon with grilled marinated shrimp, roasted asparagus & potatoes, salad, Key Lime pie; and includes one complimentary alcoholic beverage, wine or beer. Complimentary sodas, or iced tea. Doors open 6 p.m., dinner starts 6:30 p.m. RSVP required; seating limited. Tickets $69.99 pp, incl. tax and gratuity.

  • August 11 - August 14 Key West
  • 25th Annual Key West Lobsterfest
  • Website
  • Seafood lovers can chow down on Florida’s clawless lobster during a tasty “feast-ival” that features a savory schedule of events ranging from a traditional lobster boil to a lively street fair starring the sensational crustacean prepared in a variety of ways. The flavorful festivities celebrate the bounty of the Florida Keys lobster season that opens Aug. 6. Famous for its sweet and tender meat, the Keys’ spiny lobster often is served steamed with drawn butter, paired with a seasoned stuffing or cold in savory salads.

  • August 26 - August 28 Key West
  • Special Museums and Attractions Weekend
  • Website
  • Organized by WLRN, South Florida's National Public Radio affiliate, in partnership with the Florida Keys tourism council, the annual Florida Keys & Key West Museum and Attractions Weekend event provides free or value-added admission passes to participating museums and attractions in the island chain. The program is essentially a cultural pass for South Florida residents and visitors to discover the history of the Florida Keys by offering free- or reduced-admission incentives to experience over a dozen participating museums and attractions. Register free online, download and print your pass.

  • September 01 - September 05 Key West
  • Key West Brewfest
  • Website
  • Fans of beers and ales can sample about 150 of them while also discovering the flavors of the continental United States’ southernmost island. Activities ‘on tap’ include brew-focused dinners, pool parties and brunches, the lavish BrewFest Tasting Festival held Saturday on Key West’s South Beach and other enticements.

  • September 02 - September 06 Key West
  • Mel Fisher Days Commemorates 400 Years of the Nuestra Señora de Atocha
  • Website
  • Enjoy film screenings, live and silent auctions, a speakers symposium, banquet dinner and more. Meet the Fisher family and their favorite treasured authors of books exploring the shipwrecks treasures for which Mel Fisher is famous for. Complete events schedule online. Events are both free and ticketed, open to the public. All net profits go to Keys charities.

  • September 02 - September 04 Marathon
  • Florida Keys Heroes Tribute Weekend
  • Website
  • Military, fire rescue, police and medical personnel are to be honored with specially priced rooms at Hawks Cay Resort and recreational programs as part of an annual Heroes Salute Labor Day weekend. Highlights of the patriotic, “heroes in action” weekend include a family fun night, a virtual 5k Run/Walk, live entertainment by local musicians, food, games and contests.

  • September 07 - September 11 Key West
  • Womenfest Key West
  • Website
  • The popular festival for lesbians and their friends is designed to allow singles, couples and groups of women to experience the atmosphere of openness and acceptance that has made Key West an internationally acclaimed lesbian and gay vacation destination.

  • September 08 - September 08 Key West
  • Women's Fest 2022: Girly Burly Burlesque Show
  • Website
  • Staged in the Listening Room at the Key West Theater, the intimate evening of bump and grind beauties stars Tatah DuJour, Mona Amour, and the Key West Burlesque dancers, and is co-hosted by local comedian, Gwen Filosa. Special guest performances by Sheba Queen of the Night and drag king sensation, Kevin Dixon make this a "one night only" performance not to be missed. Doors open 7:30 p.m., show starts 8 p.m. Tickets start at $35 pp.

  • September 08 - September 11 Key Largo
  • Florida Keys Lionfish Derby and Festival
  • Website
  • REEF's 13th annual event will include two full days of lionfish fishing culminating in a family-friendly festival, open to the public and to include Lionfish scoring, fillet and dissection demonstrations, Lionfish tastings, Lionfish games and crafts, raffle prizes, live music and other activities and products from dozens of environmentally-minded vendors. Chefs will be providing lionfish cooking demonstrations and special dishes and drink special will be available. Early bird registration discounts are available.

  • September 10 - September 10 Islamorada
  • Swim for Alligator Lighthouse
  • Website
  • Individuals, two- and four-person relay teams have up to seven hours to complete the eight-mile roundtrip course. The course features an in-water start and a beach finish, ending shoreside during this tropical open-water swimming event.

  • September 16 - September 18 Islamorada
  • Herman Lucerne Memorial Backcountry Fishing Championship
  • Website
  • Named after the man known affectionately as “Mr. Everglades,” the event is headquartered at the Islander Resort. Anglers target fish in multiple species only in the boundaries of Everglades National Park, fishing areas that Lucerne favored. Anglers are challenged to catch at least one Tarpon, Redfish, Snook, Seatrout, Snapper, Bonefish, and Black Drum. Awards are given in 22 individual categories.

  • September 23 - September 25 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.

  • September 30 - October 01 Islamorada
  • Conch Scramble Charity Golf Tournament
  • Website
  • Floating greens, golf boats and biodegradable fish food balls highlight the annual “par-tee” on the water. 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 of four and a designated boat driver “caddy” make stops at nine Islamorada waterfront venues and come ashore to tee off. Each player has two shots at the floating holes using biodegradable golf balls that dissolve into fish food after 90 hours in the water.

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