Calendar of Events

Current Islamorada Events

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Image for Sloppy Joe’s 43rd Annual Hemingway Look-Alike Contest Image for Sloppy Joe’s 43rd Annual Hemingway Look-Alike Contest Image for Sloppy Joe’s 43rd Annual Hemingway Look-Alike Contest Image for Sloppy Joe’s 43rd Annual Hemingway Look-Alike Contest
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Image for Christopher Peterson's Eyecons at Birdcage Cabaret Image for Christopher Peterson's Eyecons at Birdcage Cabaret Image for Christopher Peterson's Eyecons at Birdcage Cabaret Image for Christopher Peterson's Eyecons at Birdcage Cabaret
Image for Hemingway 5k Sunset Run & Paddleboard Race Image for Hemingway 5k Sunset Run & Paddleboard Race Image for Hemingway 5k Sunset Run & Paddleboard Race Image for Hemingway 5k Sunset Run & Paddleboard Race
Image for 31st Annual Dolphin Tournament Lower Keys Chamber of Commerce Image for 31st Annual Dolphin Tournament Lower Keys Chamber of Commerce Image for 31st Annual Dolphin Tournament Lower Keys Chamber of Commerce Image for 31st Annual Dolphin Tournament Lower Keys Chamber of Commerce
Image for Nick Sheahan Dolphin Rodeo
  • May 3, 2024 - May 5, 2024 Islamorada Fishing
  • Nick Sheahan Dolphin Rodeo
  • Website
  • Honoring the memory of Nick Sheahan, a Florida Keys student, this tournament benefits a namesake community scholarship fund that has distributed over $408,000 to Coral Shores High School students. The event features cash prizes for the top three adult anglers with the heaviest dolphin fish. If an angler breaks the Florida dolphin fish record (81 pounds) they win the grand prize of $25,000. Register in advance online until April 29. Walk-up registration is available at the May 3, Friday night cookout and captains meeting at Tavernier Creek Marina, mile marker 90.8 bayside.
Image for Ziggy & Mad Dog's: Derby Party
  • May 4, 2024 Islamorada
  • Ziggy & Mad Dog's: Derby Party
  • Website
  • Don your best hat and turn out for the annual Kentucky Derby Party to benefit Upper Keys Humane Society at Ziggy & Mad Dog's, mile marker 83 bayside. The party, hosted by Captain Skip Bradeen, features the Best Hat and Dapper Dresser contests with fabulous prizes. A donation of $25 includes complimentary beer, wine and hors d'oeuvres.
Image for Bud N' Mary's Marina: Film Screening & Spiny Lobster Panel Discussion
Image for Matecumbe Historical Trust: "The Keys Worst Hurricanes"
  • May 14, 2024 Islamorada Arts & Culture
  • Matecumbe Historical Trust: "The Keys Worst Hurricanes"
  • 305-393-0940
  • A free presentation from the Irving R. Eyster collection will show the impacts of several Keys hurricanes, starting with the storm that hit the 1733 Spanish treasure fleet, the 1935 Labor Day hurricane, Hurricane Donna in 1960 and Hurricane Irma in 2017. These storms were some of the most destructive hurricanes in Florida Keys history, with the 1935 Hurricane being the strongest storm of the century. The presentation begins at 6 p.m. at Islamorada Public Library, mile marker 81.5 bayside.
Image for History of Diving Museum Immerse Yourself Presentation: Salvaging the Deep with Dr. Joe Dituri
  • May 15, 2024 Islamorada Arts & Culture
  • History of Diving Museum Immerse Yourself Presentation: Salvaging the Deep with Dr. Joe Dituri
  • Website
  • Retired Navy Commander Joe Dituri served continuously in active service upon various ships and stations where he was involved in every aspect of diving and special operations work, from saturation diving and deep submergence, to submersible design and clearance diving. Join Joe, who is well-known for setting the new underwater habitation record in 2023 at Jules Undersea Lodge, as he discusses salvage operations conducted during his incredible career. The presentation kicks off the museum's new featured exhibit, Salvaging the Deep. Attendees will be able to see the exhibit for its grand opening. 7 p.m. at the museum, located at mile marker 82.9 bayside.
Image for Morada Way Third Thursday Art Walk
  • May 16, 2024 Islamorada Arts & Culture
  • Morada Way Third Thursday Art Walk
  • Website
  • The Morada Way Arts & Cultural District’s Third Thursday Art Walk in Islamorada is the organization’s landmark, monthly event. On the Third Thursday of each month, Keys-inspired fine artists, vendors, residents, and visitors congregate on Morada Way in Islamorada to celebrate the arts and culture in the Florida Keys. Enjoy a relaxing evening from 6-9 p.m. perusing local fine art, imbibing local craft beer and wine and listening to music, in the area between mile markers 81 and 82.
Image for ‘Ladies Let’s Go Fishing’ Screamin’ Reels Tournament
  • May 17, 2024 - May 19, 2024 Islamorada Fishing
  • ‘Ladies Let’s Go Fishing’ Screamin’ Reels Tournament
  • Website
  • Intended for novice anglers and returning participants, this weekend is about learning and a non-intimidating, fun competition with the “Ladies Let’s Go Fishing” university organizers. Participants can join on a professional charter boat or fish on their own boat. This is a casual tournament with prizes for the heaviest offshore fish and longest inshore fish, drawings for prizes for those who caught fish, plus bonus drawings. The Friday kickoff takes place at The Tavernier Elks Club, mile maker 92 bayside; most Saturday and Sunday charters depart from Whale Harbor Marina, mile marker 83 oceanside.
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