Calendar of Events
Current Key West Events
- Sponsored Event
- Jan 25, 2025 - Jan 26, 2025 The Lower Keys
- Big Pine & Lower Keys Nautical Expo
- Website Lower Keys Chamber Grounds MM31
- 31020 Overseas Hwy Big Pine Key FL 33043
- View video
- The LKCC welcome you Saturday Jan 25 8am-4pm and Sunday Jan 26 8am-2pm to one of our biggest events with over 100 vendors. This event is fun for the whole family and includes an array of nautical pieces and much more that makes Florida Keys living great
- 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!
- Sponsored Event
- Jan 18, 2025 - Jan 19, 2025 Key West
- Key West Half Marathon & Runfest
- Website Key West Historical Seaport
- 231 Margaret Street Key West FL 33040
- 305-240-0727 E-mail
- View video
- The 27th Anniversary of the Key West Half Marathon & 5k will take place during the week-end of January 18-19, 2025. On top of previous years race day events, this years race will include the Papa’s Pilar Rum Stroll and Key West Beach N’ Beer Mile!
- 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 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 14, 2025 - Jan 25, 2025 Key West Arts & Culture
- Fringe Theater: I Love You, You're Perfect, Now Change
- Website
- A hilarious and insightful musical exploration of the epic truths and challenges of modern love and romance. Nightly showtimes 7 p.m. at Key West Armory, 600 White Street.
- Jan 14, 2025 Key West Arts & Culture
- Key West Theater: Bitch Trouble
- Website
- Writer performer Alice Johnson Boher takes you on a coming-of-age roller coaster ride of the giddy highs and codependent lows of best friendship. Told in three chronological tales, Bitch Trouble charts Alice from friendless youngster in a lame southern subdivision all the way to one-half of an iconic friend duo in the shadows of Hollywood. Performance takes place in the theater's Back Stage Listening Room. Doors open 6 p.m.; show 7 p.m. 512 Eaton St.
- Jan 15, 2025 - Jan 19, 2025 Key West Fishing
- Key West Kingfish Mayhem
- Website
- Angling teams targeting kingfish can vie for mastery and substantial cash prizes during the 2025 Key West Kingfish Mayhem tournament. The open division team that weighs in the heaviest kingfish, also known as king mackerel, is to take home a $75,000 first prize with $35,000 and $20,000 going to the second and third place teams, respectively. The tournament is headquartered at The Perry Hotel & Marina.
- Jan 16, 2025 - Jan 19, 2025 Key West
- 27th Annual Key West Half Marathon & Runfest Weekend
- Website
- Enjoy a weekend filled with running and camaraderie including 5k, 8k, 10k and half marathon races. Participants can also sign up for the Papa's Pilar Rum Stroll and the Beach N' Beer Mile, and celebrate with recovery and farewell parties.
- Jan 18, 2025 Key West Arts & Culture
- Weinerpalooza
- Website
- Key West's annual Dachshund Parade takes place Saturday, Jan. 18. All parade revelers are to gather at 11:30 a.m. in front of Customs House, 281 Front St., for a group portrait followed by the parade at 12 noon. Tails wag all along the parade route that ends at Hank's Hair of the Dog Saloon. All doggies are welcome and pet costumes are encouraged. Enjoy drink specials, raffles to benefit the Friends of Luci Fund and live entertainment.
- Jan 19, 2025 Key West Arts & Culture
- South Florida Symphony: Candide
- Website
- South Florida Symphony opens the Key West season with performs Leonard Bernstein's satirical Candide - a thrilling blend of outrageous humor, poignant storytelling and unforgettable music that follows the optimistic Candide on a globetrotting adventure of love and self-discovery. This version features the orchestra, a dynamic cast of actor-vocalists, minimal sets and costumes and a chorus performing together on stage.
- 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.
- 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 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.
- 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.
- 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 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.
- Jan 23, 2025 - Jan 16, 2025 Key West Arts & Culture
- Walk on White Third Thursday Art Walk
- Website
- Explore an array of arts-focused offerings at more than 20 locations showcasing the works of painters, photographers, sculptors, ceramic and mixed media artists, and artisan jewelry makers at this monthly third Thursday event from 6 to 9 p.m. Take in views of beautiful island architecture, exhibit openings, creative demonstrations, musical, literary and performance offerings and complimentary libations. White Street between Southard and United Streets.
- Jan 23, 2025 Key West Arts & Culture
- Key West Theater: Jon McLaughlin & Eric Hutchinson
- Website
- Acclaimed guitarist Jon McLaughlin and singer-songwriter Eric Hutchinson perform together, bringing a blend of collaborative moments with both playing on each other’s songs as well as each of them being on stage solo. Doors open at 7 p.m.; Show at 8 p.m. 512 Eaton St.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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 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.