Calendar of Events

Current Islamorada Events

Image for Key West Half Marathon & Runfest Image for Key West Half Marathon & Runfest Image for Key West Half Marathon & Runfest Image for Key West Half Marathon & Runfest
Image for NAS Key West Southernmost Air Spectacular Image for NAS Key West Southernmost Air Spectacular Image for NAS Key West Southernmost Air Spectacular Image for NAS Key West Southernmost Air Spectacular
Image for Big Pine & Lower Keys Nautical Expo Image for Big Pine & Lower Keys Nautical Expo Image for Big Pine & Lower Keys Nautical Expo Image for Big Pine & Lower Keys Nautical Expo
Image for Islamorada Fishing Club Captain's Cup Sailfish Tournament
  • Jan 14, 2025 - Jan 15, 2025 Islamorada Fishing
  • Islamorada Fishing Club Captain's Cup Sailfish Tournament
  • Dianne Harbaugh 305-522-4868 E-mail Website
  • Presented by the Islamorada Fishing Club, this is the second leg of the Florida Keys Gold Cup Series, with a field of up to 25 boat teams of elite sport fishermen. A total cash payout for a full field at the IFC Captain's Cup Sailfish Tournament could reach $25,000. Kick off is Jan. 14 with one day of fishing on Jan. 15, with the awards ceremony immediately after at the Islamorada Fishing Club.
Image for History of Diving Museum: Art Exhibit - Fintastic Fish of Florida
  • Jan 15, 2025 - Apr 16, 2025 Islamorada Arts & Culture
  • History of Diving Museum: Art Exhibit - Fintastic Fish of Florida
  • Website
  • The History of Diving Museum's latest featured exhibit, "Dive Into Art: Fintastic Fish of Florida" is on display through April 16. The exhibit features artistic creations from students across the Keys, as well as from the Art Guild of the Purple Isles. These works focus on the diverse fish of the Florida coast, along with sustainable fishing, aquaculture, and conservation.
Image for History of Diving Museum
  • Jan 15, 2025 Islamorada Environmental
  • History of Diving Museum
  • Website
  • Join Jill Kuehnert and Michaela Peterson of REEF — Reef Environmental Education Foundation —as they present actions you can take to help save Keys coral reefs. The free 7 p.m. presentation explains that small steps, like learning about marine life or contributing an hour to citizen science, can truly add up to impactful, lasting change for our oceans. Come early to see the History of Diving Museum's new featured exhibit, Dive Into Art: Fintastic Fish of Florida on its opening day. See incredible creations by students across the Keys, as well as by the Art Guild of the Purple Isles.
Image for Morada Way Third Thursday Art Walk
  • Jan 16, 2025 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. This Thursday, enjoy a holiday-flavored edition of the art walk with Keys-inspired fine artists, vendors, residents, and visitors congregating on Morada Way in Islamorada. 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 at 151 Morada Way.
Image for Baygrass Bluegrass Festival
  • Jan 17, 2025 - Jan 20, 2025 Islamorada Arts & Culture
  • Baygrass Bluegrass Festival
  • Website
  • This year's festival includes three days of music in the Morada Way Arts and Cultural District in the beer garden at Florida Keys Brewing Co., 81611 Old Hwy., from Friday, Jan. 17 through Sunday, Jan. 19; then concluding with an afternoon concert on Monday, Jan. 20 at the amphitheater at Founders Park, mile marker 87 bayside. Free admission to both venues, but there is a $10 parking charge on Monday at Founders Park.
Image for History of Diving Museum: Guided Tours of Fantastic Fish Art Exhibition
Image for Connections Project: A Mosaic of the Keys Pop-Up at Cheeca Lodge
  • Jan 21, 2025 Islamorada Arts & Culture
  • Connections Project: A Mosaic of the Keys Pop-Up at Cheeca Lodge
  • Website
  • The Florida Keys Council of the Arts Connections Project spotlights visual and performing artists throughout Monroe County at a series of pop-up events. View this year's artful mosaic of almost 100 unique canvases created by Keys artists along with performances by talented musicians at the Islamorada Chamber of Commerce's Members After Hours event at Cheeca Lodge, 81800 Overseas Highway oceanside beginning at 5:30 p.m.
Image for Coconut Cove Resort & Marina: Roaring for Rescues
Image for Island Boat Show
  • Jan 24, 2025 - Jan 26, 2025 Islamorada Fishing
  • Island Boat Show
  • Website
  • Billed as the Florida Keys’ premier boat show, Island Boat Show is held on the grounds of Island Community Church in Islamorada. Planned attractions include top boat brands and dealers, large silent auction, food and drink vendors, and nautical merchandise for the entire family. The show is open Friday from 1 to 5 p.m.; Saturday from 10 a.m. to 5 p.m.; and Sunday from 10 a.m. to 3 p.m., mile marker 83.4 bayside.
Image for Islamorada Junior Sailfish Tournament
  • Jan 24, 2025 - Jan 26, 2025 Islamorada Fishing
  • Islamorada Junior Sailfish Tournament
  • Randi Rowland-Knowles E-mail
  • The Florida Keys’ oldest sailfish tournament for kids age 16 and under celebrates its 60th year. Due to heavy winds on the previously-scheduled December dates, the tournament is rescheduled for Jan. 24-26.
Image for Pops in the Park: Afternoon Delight & Pet Parade
  • Jan 25, 2025 Islamorada Arts & Culture
  • Pops in the Park: Afternoon Delight & Pet Parade
  • Website
  • The Florida Keys Community Concert Band's Jan. 25 free Pops in the Park performance, themed “Afternoon Delight,” is to be filled with upbeat animal-themed music along with other classic and pop favorites. Bring your pets to strut their stuff in the annual pet parade during the performance. Animal Care Coalition will bring adorable adoptable pets to the performance. 4 p.m. at the amphitheater at Founders Park, mile marker 87 bayside.
Image for Connections Project: A Mosaic of the Keys Pop-Up at The Hale Gallery
Image for Swamp Guides Ball Fishing Tournament & Auction
  • Jan 31, 2025 - Feb 1, 2025 Islamorada Fishing
  • Swamp Guides Ball Fishing Tournament & Auction
  • Website
  • In this annual all-release competition, organized by the Florida Keys Fishing Guides Association, anglers target three species – bonefish, redfish and snook. The tournament benefits the Florida Keys Fishing Guides Foundation and the Guides Trust Foundation, organizations that provide funds to people in the local fishing industry in times of need. Guides are welcome to register and fish as anglers. Tournament activities take place at Safe Harbor Angler House, mile marker 80.5 bayside. The online auction is open to all, not just registered anglers.
Image for Islamorada Women's Sailfish Tournament
  • Jan 31, 2025 - Feb 2, 2025 Islamorada Fishing
  • Islamorada Women's Sailfish Tournament
  • Website
  • This challenge has female anglers facing off in Islamorada against the famous tail-dancers for trophies and prizes. The tournament kick-off takes place Friday evening at Safe Harbor Angler House, MM 80.5 bayside. Fishing takes place Saturday and Sunday, with the awards ceremony at 6:30 p.m. Sunday. Men may serve as captains and mates.
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