Calendar of Events

Current Florida Keys Events

Image for 18th Annual Sombrero Beach Run Image for 18th Annual Sombrero Beach Run Image for 18th Annual Sombrero Beach Run Image for 18th Annual Sombrero Beach Run
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 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 Truman Waterfront Farmers Market - Every Thursday
  • 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.
Image for Key West Art & Historical Society: Collecting Key West - The Works of Mario Sanchez
  • 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.
Image for Studios of Key West: Jeffrey Cardenas - On the Reef
  • 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.
Image for Key West Library Speaker Series: Mondays at 6 p.m.
  • 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.
Image for Fringe Theater: I Love You, You're Perfect, Now Change
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 Marathon Community Theater: Always a Bridesmaid
  • 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.
Image for The Southernmost Regatta
  • Jan 20, 2025 - Jan 25, 2025 Key West
  • The Southernmost Regatta
  • Website
  • Top sailing teams from around the world compete in the azure waters off Key West, showcasing colorful sails and avid sportsmanship during five consecutive days of racing. Competition is open to One Design and ORC Racing / Cruising Keelboats. Spectators can watch the races from various waterfront venues, mingle with sailors and view sailboats at the Galleon Resort's marina, 617 Front Street, after each day’s races.
Image for Florida Keys Concert Association: Famous Opera Highlights
  • Jan 20, 2025 - Jan 21, 2025 The Florida Keys Arts & Culture
  • Florida Keys Concert Association: Famous Opera Highlights
  • Website
  • The 55th season for Florida Keys Concert Association includes six concerts, each taking place in two locations. The second concert features Chelea Duo, Soprano and Joe Luis Maldonado, Barton with pianist Benedicte Jourdois, offering an evening of spine-tingling music including arias and duets from Carmen, La Traviata, The Barber of Seville and Carousel. Shows begin at 7:30 p.m. On Monday, Jan. 20, they perform at Marathon High School, 350 Sombrero Beach Rd., and on Tuesday, Jan. 21, the show is at Coral Shores High School, 89901 Old Hwy.
Image for Kelly McGillis Classic International Flag Football Championship
  • 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.
Image for Mile 0 Fest
  • Jan 21, 2025 - Jan 25, 2025 Key West Arts & Culture
  • Mile 0 Fest
  • Website
  • Mile 0 Festival is a premier music festival that celebrates Red Dirt and Americana music. Artists includes the Red Clay Strays, Randy Rogers Band, Shane Smith & the Saints, Steve Earle, Reckless Kelly, Kaitlin Butts and many more. A variety of passes that include lodging are available along with event-only passes.
Image for Key West Theater: Ben Harrison
  • Jan 21, 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.
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 Key West Theater: Melissa Etheridge
  • Jan 22, 2025 Key West Arts & Culture
  • Key West Theater: Melissa Etheridge
  • Website
  • Don't miss the legendary Melissa Etheridge on the Key West stop of her 2025 tour. Known for her confessional lyrics and raspy, smoky vocals, Etheridge has remained one of America’s favorite female singer-songwriters for more than two decades. Doors at 7 p.m.; show at 8 p.m. 512 Eaton Street.
Image for Waterfront Playhouse: The Angel Next Door
  • 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.
Image for Key West Theater: Jon McLaughlin & Eric Hutchinson
Image for Key Largo Library: Conch Shell Blowing Class
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 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 Everglades National Park Flamingo Campground: Two Nights Under the Stars
  • Jan 24, 2025 - Jan 26, 2025 Key Largo Environmental
  • Everglades National Park Flamingo Campground: Two Nights Under the Stars
  • Website
  • Join the Alliance for Florida's National Parks for an unforgettable weekend adventure. Activities include a tour of the historic Nike missile base inside the park, stargazing, kayaking, yoga, hikes, campfires, storytelling and more. Each campsite includes a picnic table and a fire ring. Bring your own tent, sleeping gear and personal supplies. Rooms may also be available at Flamingo Lodge. Tickets required to participate in the weekend programming.
Image for Old Island Restoration Foundation: January Home Tours
  • Jan 24, 2025 - Jan 25, 2025 Key West Arts & Culture
  • Old Island Restoration Foundation: January Home Tours
  • Website
  • Key West is home to what is considered the largest predominantly wooden historic district in the United States. One weekend a month, from January through March, five distinctive homes and their gardens open, revealing a range of architectural gems, eclectic art, transformed cigar-makers cottages, shipbuilders’ craft, re-imagined Victorian mansions, and the stories behind the facades. Home tour tickets provide entry to 5 homes at your self-guided pace during the Friday-Saturday tour dates. All tickets for sale online. Your receipt will be your ticket to enter the home. If you prefer to have a physical ticket, you can pick one up at the Oldest House Museum gift shop, 322 Duval St., the week before the tour date.
Image for Coconut Cove Resort & Marina: Roaring for Rescues
Image for Connections Project: A Mosaic of the Keys Pop-Up at Lower Keys Nautical Expo
Image for Tropic Cinema: Movies Under the Stars - War Games
  • Jan 25, 2025 Key West Arts & Culture
  • Tropic Cinema: Movies Under the Stars - War Games
  • Website
  • Don't miss the monthly free Movies Under the Stars screening - this month, the movie is War Games. The film will be presented free for all, outdoors on Eaton Street. Bring chairs or blankets for seating. Concessions are to be available in the theater lobby. The film begins a half hour after sunset. 416 Eaton St.
Image for Tropic Cinema: Movies Under the Stars - War Games
  • Jan 25, 2025 Key West Arts & Culture
  • Tropic Cinema: Movies Under the Stars - War Games
  • Website
  • Don't miss the monthly free Movies Under the Stars screening - this month, the movie is War Games. The film will be presented free for all, outdoors on Eaton Street. Bring chairs or blankets for seating. Concessions are to be available in the theater lobby. The film begins at approximately 6:30 p.m. 416 Eaton St.
Image for 21st annual Big Pine & the Lower Keys Nautical Expo
  • Jan 25, 2025 - Jan 26, 2025 The Lower Keys Fishing
  • 21st annual Big Pine & the Lower Keys Nautical Expo
  • 305-872-2411 E-mail Website
  • Find steals and deals on everything imaginable for boating, fishing, diving and more, from over 100 vendors. You'll also find clothing, jewelry, arts and crafts, food and beverages, and live music during the two-day event. Admission and parking are free at the Lower Keys Chamber of Commerce grounds, mile marker 31 on Big Pine Key, Saturday from 8 a.m. to 4 p.m. and Sunday 8 a.m. to 2 p.m.
Image for Schooner Wharf Bar: Wrecker's Cup Race
  • Jan 25, 2025 - Jan 26, 2025 The Florida Keys Arts & Culture
  • Schooner Wharf Bar: Wrecker's Cup Race
  • Website
  • Set your sails for the 40th annual Wrecker's Cup Race. Sailing vessels of all sizes are welcome to join the regatta. A captain's meeting is to be held Sat. night, Jan. 25, with the race beginning Sunday, Jan. 26 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.
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 Key West Cemetery Tour
  • Jan 26, 2025 Key West Arts & Culture
  • Key West Cemetery Tour
  • Historic Florida Keys Foundation 305-304-1453 E-mail Website
  • Historic Florida Keys Foundation holds its first Key West Cemetery tours of the season on Sunday, Jan. 26 at 9:30, 9:50 and 10:10 a.m. Groups of visitors will be escorted to the grave sites of Juana Borrero Pierra, William Curry, George Adderly, May Douglas, Hilda Russel and the USS Maine Monument. The 90-minute tour will cover about one mile - wear comfortable shoes. A donation of $20 to the foundation is appreciated. Reservations are required. Email hfkf@bellsouth.net or call 305-304-1453.
Image for Impromptu Classical Concerts: Simone Porter
  • Jan 26, 2025 Key West Arts & Culture
  • Impromptu Classical Concerts: Simone Porter
  • Website
  • Violinist Simone Porter has been recognized as an emerging artist of impassioned energy, interpretive integrity, and vibrant communication. In the past few years, she has debuted with the New York Philharmonic, the Philadelphia Orchestra, and the Los Angeles Philharmonic. Born in 1996, Simone made her professional solo debut at age 10 with the Seattle Symphony and her international debut with the Royal Philharmonic Orchestra in London at age 13. 4 p.m. at St. Paul's, 401 Duval St.
Image for Sheriff's Animal Farm Open House
  • Jan 26, 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.
Image for Florida Keys Concert Association: Fred Moyer, Pianist
  • 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.
Image for Winter Star Party
  • 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.
Image for Connections Project: A Mosaic of the Keys Pop-Up at The Hale Gallery
Image for Registration Opens for 7 Mile Bridge Run
  • 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.
Image for Red Barn Theatre: Ms Holmes & Ms Watson, Apt. 2B
Image for Key West Theater: Ben Harrison
  • 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.
Image for Cirque Ma'Ceo by Cavallo Equestrian Arts
  • 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.
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 Coffee Butler Amphitheater: Chicago
  • 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.
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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