Calendar of Events
Current Florida Keys Events
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- Sponsored Event
- May 02, 2025 - May 04, 2025 Islamorada
- 18th Annual Nick Sheahan Dolphin Rodeo
- Website Tavernier Creek Marina
- 90800 Overseas Hwy Islamorada FL 33070
- Becky Bohnstedt 305-393-4026 E-mail
- All proceeds to scholarships for graduating Seniors at Coral Shores High School! Friday night Kick Off Party. Music, Food, Drinks & Silent Auction. Non-Anglers welcome. $25,000 Cash Prize for angler who breaks the Dolphin State Record!
- Buy tickets! Call now!
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- Sponsored Event
- Mar 27, 2025 - Mar 29, 2025 The Florida Keys
- 2nd Annual Key West Sailfish Tournament
- Website Dante's Key West Pool Bar & Restaurant
- 955 Caroline St Key West 33040
- Brice Barr 305-304-2314 E-mail
- World-class teams will compete in this two day shoot out-style tournament, battling for the top of the leaderboard & prize money! This is the premier tournament, attracting anglers from all over Florida & beyond! Presented by Deep Eddy Vodka & Raymarine
- Buy tickets! Call now!
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- 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!
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- Sponsored Event
- Mar 27, 2025 - Mar 29, 2025 Key West
- 2nd Annual Key West Sailfish Tournament
- Website Dante's Key West Pool Bar & Restaurant
- 955 Caroline St Key West FL 33040
- Brice Barr 305-304-2314 E-mail
- World-class teams will compete in this two day shoot out-style tournament, battling for the top of the leaderboard & prize money! This is the premier tournament, attracting anglers from all over Florida and beyond! Presented by Deep Eddy Vodka & Raymarine
- Buy tickets! Call now!

- Sponsored Event
- Mar 27, 2025 - Mar 29, 2025 The Florida Keys
- 2nd Annual Key West Sailfish Tournament
- Website Dante's Key West Pool Bar & Restaurant
- 955 Caroline St Key West 33040
- Brice Barr 305-304-2314 E-mail
- World-class teams will compete in this two day shoot out-style tournament, battling for the top of the leaderboard & prize money! This is the premier tournament, attracting anglers from all over Florida & beyond! Presented by Deep Eddy Vodka & Raymarine.
- Buy tickets! Call now!
- 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 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 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.
- Feb 10, 2025 - Feb 24, 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 through March. February's featured speakers are: February 10: Ellen T. White and Leslie Tinsley. White is author of Key West: Paradise Found and Tinsley is author of more than 70 titles on American crafts and Key West Cottages and Gardens. February 17: Cheryl Lu-Lien Tan, author of Sarong Party Girls and A Tiger in the Kitchen. February 24: Michael Ruhlman, author of cookbooks and non-fiction narratives; and Ann Hood, author of memoir and fiction titles. Free to attend, no registration required. Talks take place in the library's Palm Garden, 700 Fleming St. at 6 p.m.
- Feb 15, 2025 - Mar 31, 2025 Islamorada Arts & Culture
- The Hale Gallery: P25 Collection - New Artwork by Roberto "Pasta" Pantaleo
- Website
- View the exciting new collection of paintings by Islamorada's legendary artist, Roberto "Pasta" Pantaleo. The works are to be on display through March 31 at The Hale Gallery at Ocean Sotheby's International Realty, mile marker 81.8 bayside from 10 a.m. to 4 p.m. Monday through Friday.
- Feb 18, 2025 - Mar 1, 2025 Key West Arts & Culture
- Fringe Theater: Goodnight Oscar
- Website
- There's a fine line between genius and insanity - and tonight, that line is on TV. It’s 1958 and Jack Paar hosts the hottest late-night talk show on television. It's the sweeps, so tonight's guest is wild card Oscar Levant. Just where does entertainment end and exploitation begin? Smart. Funny. Riveting. 7 p.m. at 600 White St. at the Armory.
- Feb 21, 2025 - Feb 22, 2025 Key West Environmental
- Key West Garden Club: Garden Tours
- Website
- Take a peek behind five gardens gates of private Key West homes. The Key West Garden Club hosts annual tours of select, beautiful and diverse gardens. Find tickets in advance at keywestgardenclub.com or purchase at any one of this year's garden venues.
- Feb 21, 2025 - Feb 23, 2025 Marathon
- Sombrero Beach Run Weekend
- 305-743-4582 E-mail Website
- Stocked with food, drinks, music and entertainment, the running event is to be staged Saturday, Feb. 22 at Sombrero Beach at the end of Sombrero Beach Road, mile marker 50. Awards are given to overall finishers in the 10k run, 5k run and 5k walk. Those completing the event’s 15k challenge receive special gifts. Celebrations and beach activities Friday through Sunday fill the weekend.
- Feb 22, 2025 - Feb 23, 2025 Islamorada Fishing
- Gigantic Nautical Market
- Website
- You’ll find bargains on everything nautical including clothing, fishing and diving gear, boats, motors, furniture for your boat and home, original artwork and much more. There’s fun for the entire family. Gates open at Founders Park at mile marker 87 bayside at 8 a.m. Saturday and 9 a.m. Sunday. There will be 18 food trucks spread around the park. Parking is available at Coral Shores High School with free shuttle service to the park.
- Feb 22, 2025 - Feb 23, 2025 Key West Arts & Culture
- Key West Art & Craft Festival
- Website
- The Key West Craft Show and Old Island Days Art Festival are now combined to create the Key West Art & Craft Festival. The event includes artist demonstrations, a patron comfort station with valet package check, upscale food trucks, plenty of seating, and fun events and activities for children. The location for the combined show is along the Quay at Truman Waterfront Park, 100 Southard Street.
- Feb 22, 2025 - Feb 23, 2025 Key West Arts & Culture
- Connections Project: A Mosaic of the Keys Pop-Up at Key West Art & Craft Festival
- 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 from 10 a.m. to 4 p.m. at the Key West Art & Crafts Festival at Truman Waterfront Park at the end of Southard St.
- Feb 23, 2025 The Lower Keys Fishing
- Lower Keys Rotary: Old Wooden Bridge Kids Fishing Tournament
- Website
- Don't miss this opportunity to take the kids fishing! Kids age 5 to 12 fish for free with the use of free rods and bait. Please do not bring your own rod and reel. Arrive to register between 8:30 and 9:30 a.m. Fishing takes place from 10 a.m. to noon at Old Wooden Bridge Marina, 1791 Bogie Rd. Volunteers from FWC and the Monroe County Sheriff's Department will be on hand to help the kids, and there's free food, too!
- Feb 23, 2025 Key West Arts & Culture
- Impromptu Classical Concerts: Avery Gagliano
- Website
- Avery Gagliano, pianist, is Impromptu’s 2025 “Rising Star”. Having made her debut at Carnegie Hall at the age of just 20, 22-year-old, Gagliano is an artist with ‘distinctive young talent’. Avery came to international acclaim as the First Prize and Best Concerto Prize winner at the 2020 National Chopin Piano Competition, and as the only American semifinalist at the 18th International Chopin Competition in 2021. 4 p.m., St. Paul's, 401 Duval St.
- Feb 23, 2025 Key West
- Sheriff's Animal Farm Open House
- Website
- Visit the family-friendly Monroe County Sheriff's Animal Farm, open the second and fourth Sundays of each month from 1 to 3 p.m. Animals include a capybara, possum, sloths, goats, birds and many more. Visits are free of charge, but donations of cash or fresh produce are always welcomed. Stock Island Detention Center, 5501 College Rd.
- Feb 23, 2025 Key West
- Schooner Wharf Bar: Wrecker's Cup Race
- Website
- Set your sails for the 40th annual Wrecker's Cup Race series. Sailing vessels of all sizes are welcome to join the regatta. A captain's meeting is to be held Sat. night, Feb. 22, with the race beginning Sunday, Feb. 23 at 1 p.m. An awards ceremony is to follow Sunday evening at 7 p.m. Spectators can view the action on a big screen at the bar, located at 202 William St.
- Feb 24, 2025 - Feb 25, 2025 The Florida Keys
- Florida Keys Concert Association: Esme Quartet
- Website
- The 55th season for Florida Keys Concert Association includes a selection of concerts, each taking place in two locations. The sixth and final concert in the series features the Esmé Quartet, with South Korean violinists Wonhee Bae and Yuna Ha, recently joined by the prize-winning Belgian-American violist Dimitri Murrath. Cellist Yeeun Heo completes the group as it continues its world-spanning tours.Shows begin at 7:30 p.m. On Monday, Feb. 24, they play at Marathon High School, 350 Sombrero Beach Rd., and on Tuesday, Feb. 25, they perform at Coral Shores High School, 89901 Old Hwy.
- Feb 25, 2025 Key West Arts & Culture
- Mel Fisher Maritime Museum Lecture Series: Stories from the Golden Crew
- Website
- Enjoy a panel discussion with members of Mel Fisher’s Golden Crew moderated by Carol Shaughnessy. Panelists include Tom Ford, Syd Jones, Andy Matroci and Vince Trotta. Shaughnessy will initiate and guide a lively exchange of memories as experienced by some of the key figures who worked the famed Atocha’s “main pile,” recovering priceless historic artifacts from the wreck site. Open seating. No reservation required. Doors open at 6 p.m., program at 6:30 p.m. 200 Green St.
- Feb 26, 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.
- Feb 26, 2025 - Mar 22, 2025 Key West Arts & Culture
- Waterfront Playhouse: La Cage Aux Folles
- Website
- This classic of American musical theatre is an important story about family, tolerance, love, and understanding. 407 Wall St. at Mallory Square.
- Feb 28, 2025 Key West Arts & Culture
- Coffee Butler Amphitheater: Beach Boys
- Website
- See the band whose songs forever changed the musical landscape, The Beach Boys, on the Endless Summer Gold Tour at Key West's Coffee Butler Amphitheater at Truman Waterfront Park, 21 Quay Rd. Doors open at 6 p.m.; show at 7:30 p.m .
- Feb 28, 2025 - Mar 2, 2025 Key West Arts & Culture
- Key West Orchid Festival
- Website
- The Annual Key West Orchid Festival takes place at West Martello Fort and is open to the public with free admission. Enjoy the beautiful orchids grown by locals in the show area and vote for your favorite. Find orchids and orchid supplies for sale. There will be food vendors and raffles of gorgeous blooming orchids. 10 a.m. to 4 p.m. daily. 1100 Atlantic Ave. at Higgs Beach.
- Feb 28, 2025 Islamorada Arts & Culture
- Swords & Tails - A Seaside Soiree
- Website
- The College of the Florida Keys presents the 13th annual Swords & Tails - A Seaside Soiree. The event takes place at the Islander Resort, mile marker 82, from 6 to10 p.m. This fun evening includes food, drinks, a DJ, dancing and a virtual silent auction. The theme is pirates and mermaids - which will you be? Costumes are encouraged! The event is a fundraiser for the CFK Foundation.