Calendar of Events
Current Florida Keys Events
- Sponsored Event
- Feb 22, 2025 - Feb 22, 2025 Marathon
- 18th Annual Sombrero Beach Run
- Website Sombrero Beach
- Sombrero Beach Rd Marathon FL 33050
- 305-743-4582 E-mail
- #1 Running Event of its kind in the Florida Keys! 10/15K Run & 5K Run/Walk. Events happening all weekend – kickoff party Friday, Race Day entertainment, runners breakfast/lunch, drinks, ice-cold beer, custom t-shirts, raffles & fun planned all weekend!
- Buy tickets! Call now!
- Sponsored Event
- Mar 29, 2025 - Mar 30, 2025 Key West
- NAS Key West Southernmost Air Spectacular
- Website Boca Chica Field, Key West
- Naval Air Station Key West FL 33040
- NAS Key West E-mail
- View video
- The Blue Angels & other military & civilian acts will fill the skies of the Florida Keys March 29-30th, at the NAS Key West Southernmost Air Spectacular air show at Boca Chica Field.
- Buy tickets!
- Sep 19, 2024 - Sep 25, 2025 Key West
- Truman Waterfront Farmers Market - Every Thursday
- Website
- Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.
- Dec 6, 2024 - May 18, 2025 Key West Arts & Culture
- Key West Art & Historical Society: Collecting Key West - The Works of Mario Sanchez
- Website
- Mario Sanchez (1908-2005), a Key West native, is among this country’s finest and most-recognized folk artists. In hundreds of intricately painted wood carvings created in a lifelong labor of love, Sanchez has provided a better history of Key West in the first part of the 20th century than any annals or academic texts. His bas-relief carvings, or intaglios, are a visual feast filled with the music, smells and passion of Gato’s Village, the Cuban-American community of Key West where Sanchez spent much of his life. In the carvings, each person, chicken, dog and fish has its own singular expression, attitude and identity. The exhibit is on display at the Custom House Museum daily from 10 a.m. to 5 p.m. 281 Front St.
- Jan 2, 2025 - Jan 30, 2025 Key West Arts & Culture
- Studios of Key West: Jeffrey Cardenas - On the Reef
- Website
- Key West resident Jeffrey Cardenas has traveled from Polynesia to the Mediterranean and Caribbean Sea, photographing vibrant coral reef ecosystems. His work reveals the beauty and essential role of coral reefs in supporting diverse marine life, prompting reflection on their significance and the urgent need for their conservation. 533 Eaton St.
- Jan 13, 2025 - Jan 27, 2025 Key West Arts & Culture
- Key West Library Speaker Series: Mondays at 6 p.m.
- Website
- Authors in the Key West Library Speakers series appear on Mondays, January through March. January's featured speakers are: January 13: Ayana Mathis, author of The Unsettled (Knopf, 2023), named a New York Times and Washington Post Notable Book of 2023. January 20: Jimin Han, author of The Apology, named best book of the summer by the Los Angeles Times, Vanity Fair and others. January 27: Cathy Salustri in conversation with David Sloan - Salute is author of Florida Spectacular: Extraordinary Places and Exceptional Lives. Free to attend and no registration required. Talks take place in the library's Palm Garden, 700 Fleming St. at 6 p.m.
- 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.
- Jan 16, 2025 - Feb 8, 2025 Marathon Arts & Culture
- Marathon Community Theater: Always a Bridesmaid
- Website
- This comedy follows four Southern high school friends who vow serve as bridesmaids in each other's weddings, no matter what. Fast forward to 30 years later, they are still determined to honor their vow and navigate the challenges of love and marriage as bridesmaids through multiple weddings. Showtimes at 8 p.m. 5101 Overseas Hwy.
- Jan 21, 2025 - Jan 27, 2025 Key West LGBTQ
- Kelly McGillis Classic International Flag Football Championship
- Website
- Women from countries far and wide will be descending upon Key West for the 32nd annual flag football competition with teams participating from USA, Morocco, Spain, Mexico, Sweden, Pakistan, Mexico, Honduras and El Salvador. Kelly McGillis will serve as grand Marshall for the players' parade from the historic seaport down Duval Street on Thursday, Jan. 25. Game activities throughout the weekend Jan. 26-28 are free for the public to attend at Wicker Field Sports Complex on Kennedy Drive off Flagler Ave.
- Jan 22, 2025 - Feb 8, 2025 Key West Arts & Culture
- Waterfront Playhouse: The Angel Next Door
- Website
- The wonderfully funny script by Paul Slade Smith captures the joy and wit of 1940s screwball comedies. Brace yourself for what a critic called "a perfect storm of comedic chaos, irresistible charm and rapid-fire banter." Showtimes 8 p.m. plus a 2 p.m. matinee on Feb. 1. 407 Wall St. at Mallory Square.
- Jan 27, 2025 - Feb 2, 2025 The Lower Keys Environmental
- Winter Star Party
- Website
- Astronomers and astrophotographers from around the globe gather in the Lower Florida Keys to enjoy 180-degree viewing of the Southern Cross and other constellations, comets and stars during the Winter Star Party.
- Jan 27, 2025 Islamorada Arts & Culture
- Connections Project: A Mosaic of the Keys Pop-Up at The Hale Gallery
- 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 mosaic of almost 100 unique canvases created by Keys artists along with performances by talented musicians at The Hale Gallery at Ocean Sotheby's Realty, 81800 Overseas Highway bayside beginning at 5:30 p.m.
- Jan 27, 2025 - Jan 28, 2025 The Florida Keys Arts & Culture
- Florida Keys Concert Association: Fred Moyer, Pianist
- Website
- The 55th season for Florida Keys Concert Association includes a selection of concerts, each taking place in two locations. The third concert in the series features Frederick Moyer. During more than thirty years as a full-time concert virtuoso, Moyer has appeared as piano soloist with numerous world-renowned orchestras in all parts of the globe. A consummate communicator and educator, he is one of the concert association's favorite artists and is returning with his magnificent performances of classical music. Shows begin at 7:30 p.m. On Monday, Jan. 27, he plays at Marathon High School, 350 Sombrero Beach Rd., and on Tuesday, Jan. 28, the show is at Coral Shores High School, 89901 Old Hwy.
- Jan 28, 2025 Marathon
- Registration Opens for 7 Mile Bridge Run
- Website
- Registration opens on Tuesday, January 28, 2025 beginning at 6 a.m. Anyone can register on this date, but race organizers are only able to accept 1,500 entries and the field fills very quickly. Sometimes the registration is filled within minutes, so please be online and ready. You must show a PHOTO ID when picking up your bib number that matches the same address you used to register.
- Jan 28, 2025 - Feb 22, 2025 Key West Arts & Culture
- Red Barn Theatre: Ms Holmes & Ms Watson, Apt. 2B
- Website
- Fast-paced and wildly entertaining, this take on Sir Arthur Conan Doyle’s famous sleuth and sidekick re-examines the classic adventure stories you love through a bold new female lens. Shows at 7:30 p.m. 319 Duval St.
- Jan 28, 2025 Key West Arts & Culture
- Mel Fisher Maritime Museum Lecture Series: Before Juneteenth with Dr. Corey Malcom
- Website
- A showing of the mini-documentary that tracks the timeline of emancipations and their celebrations in Florida with introduction and followup conversation focusing on emancipation in Key West led by Corey Malcom, Ph.D. The Lead Historian for the Florida Keys History Center and Director of Archaeology at the Mel Fisher Maritime Museum, Malcom is featured in the film.? Open seating, no reservation needed. Doors open at 6 p.m., program at 6:30 p.m. 200 Greene St.
- Jan 29, 2025 - Feb 2, 2025 Marathon Arts & Culture
- Cirque Ma'Ceo by Cavallo Equestrian Arts
- Website
- Experience the magic with this emotionally charging, up close and personal experience. Step into the exclusive, custom designed Italian Big Top theater and settle back in brand-new, state of the art seating. The world of Ma’Ceo is proud to showcase mesmerizing acrobatic feats, aerial dancing, and exotic horses. Come feast your senses on the beauty and mystery through the adventure of Cirque Ma'Ceo. Showtimes vary. San Pablo Catholic Church, 550 122 Street Ocean.
- Jan 29, 2025 Key West Arts & Culture
- Key West Theater: Ben Harrison
- Website
- Ben Harrison is a playwright, lyricist and composer who is also an entertainer. What makes his live performances so enjoyable is that, at his core, he is a barroom guitar player/singer/songwriter who somehow manages to blend history, musical theater, Key West and humor into unusual stories that are mostly true. Key West Theater's Backstage Listening Room. Doors at 6 p.m.; show at 7 p.m. 512 Eaton Street.
- Jan 31, 2025 Key West Arts & Culture
- Coffee Butler Amphitheater: Chicago
- Website
- Hailed as one of the most important bands in music since the dawn of the rock and roll era, the legendary rock and roll band with horns, Chicago, came in as the highest charting American band in Billboard Magazine's Top 125 Artists Of All Time. And, Chicago is the first American rock band to chart Top 40 albums in six consecutive decades. Doors open at 6:30 p.m.; show at 8 p.m. 21 Quay Rd.
- 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.
- 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.