Florida Keys Events

Events in the Florida Keys

Fantasy Fest

The grandaddy of all events takes in Key West, and is called Fantasy Fest. Nothing is more eagerly awaited than the opening of Fantasy Fest each October. This Halloween celebration combines elements of Mardi Gras and the Miami club scene, resulting in a wild party filled with costumes, parades, and rum runners (Captain Morgan sponsors). Parades of brightly-bedecked revelers flow down Duval and Whitehead Streets while other celebrants toss beads from balconies. You’ll have to make reservations far in advance for this party.

The Pirates in Paradise Festival takes over Key West’s historic seaport and Fort Zachary Taylor State Park & Beach and celebrates the official end of the hurricane season. Spanning November & December, this melee of pirate ships and buccaneers culminates in the Fort Taylor Pirate Feast & Shipwreck Ball. Other events include a pirate market, maritime art exhibits, a writer’s workshop, historic re-enactments, and more.

The Island Jubilee, also in November, is an arts & crafts festival in Key Largo’s Harry Harris Park. Live musical and theatrical performances.

The Key West Literary Seminartakes place each January, and features panels, readings, and literary parties (this is Key West, after all!). There’s a theme each year, and the participants are respected members of their fields. Past themes were Travel Writing and Biography. They also sponser a Writer’s Walk, which is a guided tour of famous literary sites in Key West. It’s about a one-mile walk.

Other annual events include the Birding & Wildlife Festival in October, Florida Keys Jazz and Blues Festival (in April on Plantation Key, and in October on Islamorada), and the Florida Keys Heritage Festival in January. Marathon even sponsors a Florida Keys Renaissance Faire on Sombrero Beach in January. Don’t miss the daily Sunset Celebrations held at Mallory Square in Key West.

Key West also sponsors the Hemingway Days Festival in July. In the spirit of the Ernest Hemingway that Key West knew and loved, there are arm-wrestling contests, costume parties, and short-story competitions. Of course there’s the Papa look-alike contest, where white-bearded man over a certain age show up and do their best to look Hemingway-like. The costume parties encourage people to dress up as Hemingway charaters…Key Westers love to dress up!

  • 2/20/2018 Florida Keys Concert Association presents: Attacca Quartet
    This internationally acclaimed prize-winning New York-based string quartet has become one of America's premier young performing ensembles. Show starts 7:30 PM, at Island Community Church, 83250 Overseas Highway, (MM83). Tickets to be available online.
  • 2/22/2018 - 3/10/2018 Waterfront Playhouse presents: Hand to God
    Sesame Street meets The Exorcist in this outrageous comedy. Hand To God tells the story of an awkward Texas teen named Jason, who spends his afternoons at his local church, practicing for the Christian Puppet Ministry run by his widowed mother. All hell literally breaks loose, however, when Jason's puppet Tyrone takes on a shocking and dangerously irreverent personality all its own. Nominated for five Tony Awards including Best Play, Hand To God explores the startlingly fragile nature of fai
  • 2/23/2018 - 2/24/2018 Key West Garden Club Gardens Tour
    Between 10 a.m. and 3 p.m., both days, attendees can explore the oceanfront site at 1100 Atlantic Blvd. that has been the garden club's headquarters for more than a half-century. The bricks and archways of the Civil War--era fort are the backdrop for spectacular orchids and bromeliads, stands of black bamboo, indigenous plants, a peace garden and a dramatic new pool and fountain in addition to many other attractions.
  • 2/23/2018 - 2/24/2018 Spring Backcountry Fly Championship Series
    Tournament anglers are to compete to catch the most inches of snook and redfish on fly in a challenge where one inch equals one point. Awards are to be given to the grand champion and runner-up, and to the anglers who catch the largest snook and redfish. The field is limited to 30 boats.
  • 2/24/2018 Fitness for a Cause: Paws in the Park
    Join the Marathon campus of the Florida Keys SPCA in Key Colony Beach for the inaugural mile walk for the animals. Bring your well behaved four-legged pet on a leash or just join them on two legs for outdoor fitness and to help raise money to support adoption, spay/neuter, behavior, foster, humane animal control and outreach programs. Registration begins at 9 a.m., at City Hall Park. Suggested donation $10.
  • 2/24/2018 - 2/25/2018 Rotary Gigantic Nautical Flea Market
    Thousands of bargain hunters are expected to browse and buy fishing gear, rods, reels, line, lures and tools. Hours are 8AM - 3PM. Event is staged at Founders Park, MM 87. Free Parking at Coral Shores High School (MM 90). Free shuttle to the park. A $5 per adult donation requested on entry.
  • 2/24/2018 - 2/25/2018 53rd Annual Old Island Days Art Festival
    The 53rd annual juried outdoor fine art festival features oil paintings, watercolors, sculpture, photography and other offerings by more than 100 artists from around the United States and beyond. The event takes place on lower Whitehead Street in historic Old Town.
  • 2/25/2018 Key West Impromptu Concerts presents: Katona Twins
    The identical twins Peter and Zolta?n Katona were born in Budapest, Hungary, in 1968, and began their musical education at the age of ten. As the Katona Twins they've put out nine CDs so far, covering a wide spectrum of music ranging from Mozart, Bach, and Scarlatti, to Queen, the Doors, and the Beatles They have deservedly become among the classical guitar world's musical "must see" performers. They have been called "A symphony for two, Twin Peaks of Classical Music." Show starts 4 p.m., St. Pa
  • 2/26/2018 Florida Keys Concert Association presents: Fandango
    A toe-tapping spicy mix of Latin, Spanish, Sephardic, Balkan, and classical sounds played on flute, violin, guitar and cello. Founded by four multi-award-winning, globe-trotting virtuosi who hail from Spain, Bosnia, UK and USA, they have played separately and together on the world's most prestigious stages. Show starts 7:30 PM, at Marathon High School, 350 Sombrero Road, (MM50). Tickets to be available online.