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Events in the Florida Keys

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

Events in Florida Keys for 2021

  • August 11 - August 15 Key West
  • Tropical Heat
  • Website
  • Tropical Heat offers 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 pool parties to a sunset cruise to late-night gatherings at the island’s LGBTQ bars and nightclubs.

  • August 12 - August 15 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 25 - August 25 Key West
  • Fee-Free Day at Everglades and Dry Tortugas National Parks to Commemorate National Parks' Birthday
  • Website
  • Celebrate the National Park Service's 105th birthday! National parks across the country will be hosting in-park programs and virtual experiences. Entrance fees are waived. Everglades National Park normally charges $30.00 per vehicle or vessel, $25.00 per motorcycle, and $15.00 per person for pedestrians, cyclists and paddle-craft, for a 7-day pass. Dry Tortugas National Park normally charges $15.00 per person over the age of 16, which is good for 7 days. Fees are ordinarily included in the ticket prices for ferry and seaplane tours, but they will not be included on fee free days.

  • September 01 - September 05 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 03 - September 05 Marathon
  • Florida Keys Heroes Tribute Weekend at Hawks Cay Resort
  • Website
  • Military, fire rescue, police and medical personnel are to be honored with specially priced rooms 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. Events are open to the public.

  • September 09 - September 12 Islamorada
  • Florida Keys Lionfish Derby and Festival
  • Website
  • REEF's 12th annual event will include two full days of lionfish fishing culminating in a family-friendly festival at picturesque Postcard Inn Resort & Marina. The festival is open to the public and will include Lionfish scoring, fillet and dissection demonstrations, Lionfish tastings, Lionfish games and crafts, raffle prizes, and other activities and products from 30 environmentally-minded vendors. Chefs will be providing lionfish cooking demonstrations and special dishes and drink special will be available. Live Music by South Florida's Soulgrass Band The Copper Tones. Early bird registration discounts are available, before July 9.

  • September 10 - September 12 Key West
  • Robert James Sales S.L.A.M. Celebrity Tournament
  • Website
  • In the first of three tournaments in the annual Redbone Celebrity Tournament Series, also called The Trilogy, anglers target tarpon, permit and bonefish to achieve the coveted “flats grand slam.” The event raises funds for the fight against cystic fibrosis.

  • September 11 - September 11 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.

  • September 17 - September 19 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 at our ceremony hosted at the Islander Resort.

  • September 18 - September 18 Big Pine Key
  • RESCHEDULED : 37th Annual Underwater Music Festival
  • Website
  • This annual event for both divers and snorkelers is staged at Looe Key Reef, an area of the Florida Keys National Marine Sanctuary about 6 miles south of Big Pine Key. Hosted by the Lower Keys Chamber of Commerce and a local radio station, US1 104.1 FM, the ocean celebration encourages environmentally responsible diving and preservation of the world’s coral reefs. While the festival’s primary purpose is to promote reef protection and eco-conscious diving, it also offers a bucket-list underwater experience. Some participants might even spot “mermaids” and other costumed characters swaying beneath the waves, adding visual excitement to the unique conservation concert.

  • 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.

  • September 24 - September 25 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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