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Events in Key West

Event calendar provided with the courtesy of the Monroe County Tourist Development Council.

Events in Key West for 2024

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  • December 04 - Mar 05, 2024 Key West
  • Monday & Tuesday Evening Glow Hours at Hugh's Rooftop
  • Website
  • The Studios of Key West's Hugh's Rooftop offers the best views in town and an ideal spot to catch the sunset and a drink on Monday and Tuesday evenings from 5 to 7 p.m. through March 5. The bar is open and admission is free. Capacity is limited, so come early. 533 Eaton Street.

  • December 15 - Feb 11, 2024 Key West
  • Key West Museum of Art & History: Our Working Waterfront
  • Website
  • The "Our Working Waterfront" exhibit opens Dec. 15 with a free reception from 5 to 7 p.m. at the Customs House Museum, 281 Front St. The exhibit explores the diversity of maritime industries and occupations along the Key West waterfront and reveals the complex interconnections of seafront work, while integrating never before exhibited historic photos and a range of special artifacts from the museum's permanent collection. The exhibit continues through Feb. 11.

  • December 19 - Jan 13, 2024 Key West
  • Red Barn Theatre: A Tuna Christmas
  • Website
  • In the third-smallest town in Texas, radio station OKKK news personalities report on Yuletide activities.The hilarity never lets up in this comedic romp for all seasons featuring many colorful Tuna denizens played by two very funny actors, Brandon Beach and David Black. Showtime 8 p.m. Tickets $49 to $60.

  • January 04 - 25, 2024 Key West
  • The Studios of Key West: It's in the Bag!
  • Website
  • This colorful, irreverent exhibit conceived by writer Kevin Assam asks Key West artists to reimagine the “bags and baggage” they have schlepped, constructed, and embedded in their daily lives. Your favorite Key West creatives present inventive two and three-dimensional works inspired by the theme for one of the most fun exhibits this season. Find the exhibit in The Studios' Zabar Lobby Gallery, 533 Eaton St.

  • January 04 - 25, 2024 Key West
  • The Studios of Key West: The State of Our Nature
  • Website
  • Kristen B. Grace’s photographs of native flora and fauna, plus Indigenous Floridian artworks are presented with Heather Dewar’s elegant captions telling stories of Florida’s evolution, survival, adventure and scientific discovery. The writer and photographer are co-authors of the Florida Book Award’s 2022 Gold Medal in Visual Arts winner, “All Things Beautiful.” The exhibition aims to highlight the importance of conserving Florida’s heritage in a state of environmental change. Find the exhibit in The Studios' Zabar Project Gallery. 533 Eaton St.

  • January 09 - 10, 2024 Key West
  • The Studios of Key West: David Wilcox in Concert
  • Website
  • Folk singer-songwriter David Wilcox’s lyrical insight is matched by a smooth baritone voice and virtuoso guitar playing, giving him a range and tenderness rare in folk music. More than twenty albums into a career spanning over 30 years of touring extensively around the U.S and world, he continues to deliver joy, inspiration and invention to his legions of fans. Tuesday night at 7 p.m. in Helmerich Theater; Wednesday night at 6 p.m. on the roof at Hugh's View. Ticket prices vary. 533 Eaton St.

  • January 10 - 20, 2024 Key West
  • Fringe Theater: 5 Lesbians Eating a Quiche
  • Website
  • A tasty recipe of hysterical laughs, sexual innuendos, and delicious discoveries are served up at the 1956 annual quiche breakfast of the Susan B. Anthony Society for the Sisters of Gertrude Stein. Winner of the 2021 New York International Fringe Festival. Tickets $45 to $60. Showtime 7 p.m. at the Armory, 600 White St.

  • January 11 - 14, 2024 Key West
  • Key West Kingfish Mayhem
  • Website
  • Angling teams targeting kingfish can vie for mastery and substantial cash prizes during the 2024 Key West Kingfish Mayhem tournament. Slated for Thursday through Sunday, Jan. 11-14. The open division team that weighs in the heaviest kingfish, also known as king mackerel, is to take home a $10,000 first prize.

  • January 11 - 14, 2024 Key West
  • Key West Literary Seminar: Florida - The State We're In
  • Website
  • Readers and writers gather every January for this festive four-day literary celebration. This year's theme is: “Florida: The State We’re In.” Attendees will find a cast of novelists, poets, historians, humorists, and cultural critics who know the Sunshine State better than anybody. Featured authors include Dave Barry, Carl Hiaasen, Craig Pittman, Diane Roberts, Campbell McGrath and others. Most seminar events take place at Coffee Butler Amphitheater at Truman Waterfront Park, 21 Quay Road. Tickets are available for the full seminar program. Several seminar programs - to be announced closer to the event - will be open to the public for no charge.

  • January 12 - 13, 2024 Key West
  • Key West Home Tours
  • Website
  • The Old Island Restoration Foundation’s Key West Home Tours are among America’s oldest and longest-running, dating from 1960. This 64th series features self-guided tours of several Key West homes and gardens. Home Tour tickets provide entry to 5 homes at your self-guided pace, between 1-4 p.m. during the Friday-Saturday tour. $55 per person. Addresses of featured homes are to be provided when tickets are purchased.

  • January 13 Key West
  • The Studios of Key West: One Music Family
  • Website
  • Ralph De Palma presents an epic night of music celebrating the release of The Soul of Key West: Vol III, the latest in his series of books documenting the Key West music scene through richly textured photography and stories from the musicians themselves. The event begins at The Studios' Helmerich Theater from 7 to 8 p.m. with a book signing celebration, followed by musical performances from 8 until 10 p.m. Tickets $30 to $75. 533 Eaton St.

  • January 13 - 14, 2024 Key West
  • 18th Annual Florida Keys Seafood Festival
  • Website
  • Bring the whole family for the freshest seafood caught, cleaned, prepared and served by local fishermen, along with live music both days, plus a kids eco-discovery zone and great shopping and art. Hours on Saturday are 11 a.m. to 7 p.m., and Sunday 11 a.m. to 5 p.m. $10 admission is good for both days and includes entry in a raffle for $250 worth of seafood. The festival takes place at Bayview Park, 1320 Truman Ave.

  • January 14 Key West
  • 26th Annual Key West Half Marathon & Runfest
  • Barbara Wright 305-240-0727 Email Website
  • Recognized by Runners World magazine as one of the 10 great half-marathons of the winter season, the 2024 race follows a 13.1-mile course that includes the Southernmost Point, Duval Street, Smathers Beach and more. The race typically attracts American and international runners to compete in Key West's balmy January climate. Other events include the 5k along with the Rum Stroll and Beach N' Beer Mile events.

  • January 14 Key West
  • Sunset Green: Cool Down & Recover Pool Party
  • Website
  • Key West Half Marathon and 5k race participants and the public are invited to a free Cool Down & Recover pool party at the Sunset Green Event Lawn, 3820 N. Roosevelt Blvd. from 4 to 6 p.m. Enjoy live music and drink specials and cool down in the pool.

  • January 15 - 19, 2024 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.

  • January 17 - 20, 2024 Key West
  • RokIsland Fest
  • Website
  • More than 20 of the best and most iconic rock bands and performers bring their massive hits to the Southernmost City in the U.S. for four days of unforgettable songs, sun & sand at RokIsland Fest. The lineup includes Bret Michaels, Styx, Stone Temple Pilots, Night Ranger, Don Felder and many more. Multi-day passes with and without rooms and VIP experiences are available, with most performances at Truman Waterfront Park, 21 Quay Rd.

  • January 17 - 20, 2024 Key West
  • Red Barn Theatre: This One's for the Girls - The Women of Country Music
  • Website
  • Christine Mild returns with a new show featuring the best of women who sing country . . . their stories and their incredible music. She sold out her Patsy Cline show last season so don't miss this one! Starring Christine Mild with Musical Direction by Jim Rice, Gary Rivenson on bass and Gary McDonald on drums. Tickets $75. Showtime 8 p.m. 319 Duval Street.

  • January 18 Key West
  • Key West Art & Historical Society: Happy Hour With the Historian
  • Website
  • Join historian Dr. Cori Convertito for a talk that explores the diversity of work historically done along the Key West waterfront, including shipbuilding, wrecking, sponging, turtling and shrimping. Important questions will be addressed about how the waterfront has changed over time, the reasons for these changes, and implications for the future. $15 ticket includes one glass of wine, beer or a soft drink. 5 to 6 p.m. at Comedy Key West, 218 Whitehead St.

  • January 20 Key West
  • South Florida Symphony: Brahms, Bach, Montgomery & Price
  • Website
  • South Florida Symphony Orchestra kicks off its 26th Key West Season with the works of two trailblazing composers: Florence Price, the first African American female to have a work premiered by a major U.S. orchestra, and Jessie Montgomery, one of today’s most compelling composers. The stage comes alive as virtuoso pianist Awadagin Pratt presents Montgomery's latest piano concerto alongside another Symphony premiere, Bach’s Keyboard Concerto No. 4. All of this is anchored by Brahms' lyrically beautiful Symphony No. 1. Tickets start at $25. Tennessee Williams Theatre, 5901 College Rd. Curtain time is 7:30 p.m.

  • January 21 Key West
  • Tennessee Williams Theatre: Paradise Big Band
  • Website
  • Under the baton of Joe Dallas Jr, the band consists of professional and semi-professional musicians from the Lower Keys and Key West. In the interest of enhancing both solo and ensemble performances, the band regularly features outstanding guest artists from New England, New York City and Pittsburgh. Tickets $30 and $40. Showtime 8 p.m. 5901 College Rd.

  • January 22 - 29, 2024 Key West
  • Kelly McGillis Classic
  • 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.

  • January 23 - 28, 2024 Key West
  • Key West Food & Wine Festival
  • Website
  • The festival includes over 20 unique events taking place across the southernmost island city, including waterfront wine tastings, winemaker/chef collaborations, local events that present an authentic taste of Key West, and an amazing grand tasting event. The theme for 2024 is España, celebrating the wine and culture of Spain and Spain's impact on Key West. Tickets are available to individual events, each celebrating the food and wines of Spain along with renowned Spanish artists, and one event themed around Ernest Hemingway's time spent in Spain.

  • January 23 - 27, 2024 Key West
  • Mile 0 Fest
  • Website
  • With a carefully curated line-up of well-known and up-and-coming artists, Mile 0 Fest offers an unforgettable music experience. The event’s “Mile 0” moniker refers to Key West’s location at “mile 0” of U.S. 1. Tickets are selling fast, with Platinum and Premiere Packages sold out. Pirate and Beach Bum packages are still available, along with single day passes. Talent includes Morgan Wade, Tanner Usery, the Randy Rogers Band and many more.

  • January 24 - Feb 17, 2024 Key West
  • Waterfront Playhouse: Singing in the Rain
  • Website
  • Filled with every memorable moment from the film and a downpour of unforgettable songs, including ‘You are My Lucky Star’, ‘Fit as a Fiddle’, and ‘Make Em Laugh’, the “Greatest Movie Musical of All Time” will hit the the Waterfront stage and yes – it will rain! Tickets $40 to $85. Showtimes at 8 p.m., along with one Saturday matinee Feb. 3. 407 Wall Street at Mallory Square.

  • January 24 Key West
  • Tennessee Williams Theatre: The Midtown Men
  • Website
  • The Midtown Men Tenth Anniversary Tour reunites stars from the Original Broadway Cast of the smash hit musical, Jersey Boys. Highlighted with their own high octane arrangements, slick moves and one of a kind repartee, the group's all new concert features even more iconic 60s music from The Beatles, The Beach Boys, Chicago, Elvis, The Temptations, The 4 Seasons and more. Tickets $35 to $155. Showtime 8 p.m. 5901 College Rd.

  • January 26 Key West
  • Tennessee Williams Theatre: Puppy Pals, Live!
  • Website
  • As seen on "America’s Got Talent," Puppy Pals is coming to town. It's 60 minutes of Dogs Gone Wild and Humans Gone Crazy! There will be a special meet and greet after the show with your favorite Puppy Pals for photos and ‘paw’ shakes. Tickets $25 to $95. Showtime 7 p.m. 5901 College Rd.


  • January 30 - Feb 03, 2024 Key West
  • Key Western Fest
  • Website
  • The 2024 Key Western Fest has a dream lineup including some of the best female voices and songwriters in the country music genre. Artists include Wynona Judd, Tanya Tucker, Jo Dee Messina, Sara Evans, Terri Clark, Deana Carter, Lorrie Morgan, Pam Tillis, Suzy Bogguss and many more. Full experience packages are on sale that include a five-day festival pass (opening night kick-off included), five nights of lodging, live-music sails on a cruising catamaran and more. For those wishing to handle their own accommodations and excursions, a “pass-only” option is available. Main performances are at Coffee Butler Amphitheater, 21 Quay Rd. at Truman Waterfront Park.

  • January 31 - Feb 24, 2024 Key West
  • Red Barn Theatre: POTUS
  • Website
  • One four-letter word is about to rock the White House into a global crisis. Seven brilliant and beleaguered women risk life and sanity to keep POTUS out of trouble in this gleefully filthy and outrageously funny farce. A recent Broadway smash hit! Showtimes at 8 p.m. Tickets $49 to $70. 319 Duval Street.

  • February 09 Key West
  • The Studios of Key West: Anne McKee Fine Art Auction
  • Website
  • This popular art auction features original paintings, sculpture, photography, fiber arts, ceramics, mixed media, jewelry pieces and more created by celebrated and renowned local masters to fresh new Florida Keys emerging artists. Proceeds are divided with half going directly to the artist, and the other half to the Anne McKee Artists Fund, supporting grants for projects by local artists in the visual, performance and literary arts. Doors open at 4:15 p.m. with the auction starting at 5 p.m. 533 Eaton St.

  • February 12 Key West
  • Coffee Butler Amphitheater: Willie Nelson
  • Website
  • Willie Nelson and family return to Key West's amphitheater for one night, Monday Feb. 12. Experience the magic as this living legend shares his music and stories from a remarkable career that has touched the hearts of millions. Tickets available online. Showtime 7 p.m. 21 Quay Rd.

  • February 13 - 14, 2024 Key West
  • The Studios of Key West: Rodney Crowell in Concert
  • Website
  • Crowell came to prominence in Nashville in the 70s as a songwriter before establishing himself as a critically-acclaimed solo artist. He has 15 number-one hits to his credit and tracks recorded by the likes of Johnny Cash, Waylon Jennings, Emmylou Harris and Willy Nelson. NPR declare him the "elder statesman of the Americana scene." Performances Tuesday at 7 p.m. in Helmerich Theater and Wednesday at 6 p.m. on the roof at Hugh's View. Ticket prices vary, starting at $85. 533 Eaton St.

  • February 14 Key West
  • Wesley House Family Services Valentine's Day Gala
  • Website
  • Take your special someone to the annual Wesley House Gala Family Service's Valentine's Day Gala. The "Keys Formal" event features the island's largest silent auction, open bar, live music and dancing, and an elegant dinner designed and prepared by Catered Affairs. Custom House Museum, 6 to 9:30 p.m. 281 Front Street.

  • February 14 Key West
  • Tennessee Williams Theatre: A String Quartet Plays Love Songs
  • Website
  • Indulge your special someone in an enchanting evening as the string quartet weaves a musical tapestry of love songs across genres. From timeless classical favorites to cinematic melodies and your favorite love ballads, experience the universal language of love as the strings serenade you and your Valentine to the sweet sounds of Elvis Presley, Lady Gaga, Puccini and many more.

  • February 15 - 19, 2024 Key West
  • Presidential Families Weekend
  • Website
  • A series of special events takes place over Presidents' Day Weekend at the Harry S. Truman Little White House. On Thursday, Feb. 15, there is a kickoff "Happy Hour at Harry's" cocktail and trivia event. Sat. Feb. 17, a panel of presidential descendants discusses "Political Maneuvering." Other weekend highlights include Clifton Truman Daniel, the grandson of Harry S. Truman, performing the acclaimed stage production, "Give 'Em Hell, Harry!" on Sunday and Monday, and a Sunday presentation by artist Tom Corbin, who sculpted the monumental Harry Truman bronze in the U.S. Capitol Rotunda. There will also be a traditional President's Day cookout on Monday, Feb. 19 from 11:30 a.m. to 1:30 p.m. with picnic-style food available for purchase. Find more event information and ticket sales online. 111 Front Street, Key West.

  • February 16 - 17, 2024 Key West
  • Key West Home Tours
  • Website
  • The Old Island Restoration Foundation’s Key West Home Tours are among America’s oldest and longest-running, dating from 1960. This 64th series features self-guided tours of several Key West homes and gardens. Home Tour tickets provide entry to 5 homes at your self-guided pace, between 1-4 p.m. during the Friday-Saturday tour. $55 per person. Addresses of featured homes are to be provided when tickets are purchased.

  • February 16 Key West
  • Tennessee Williams Theatre: Drum Tao
  • Website
  • Drum Tao combines the unique sounds of Japanese Taiko drums with flute, harp and guitar, along with energizing choreography, vibrant sets and contemporary costuming, to create a large-scale performance experience that captivates audiences' eyes and ears. Tickets $35 to $145. Showtime 8 p.m. 5901 College Rd.

  • February 22 - 23, 2024 Key West
  • Fringe Theater: Key West Characters - True Stories
  • Website
  • An evening of short plays, monologues and musical tributes that celebrate Key West. True stories include portrayals of Mrs. Ellen Sanchez, Bette Page, Sushi, Fats Navarro, Frank Merlo and more. Tickets $35. Doors at 6:30, seating is first-come, first seated for this special, community-focused program at Williams Hall, 729 Fleming St.

  • February 24 - 25, 2024 Key West
  • 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 and Craft Festival. This new 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.

  • February 24 Key West
  • Tennessee Williams Theatre: Mike Super, Illusionist
  • Website
  • Through spectacular illusions and his down-to-earth style and personality, Mike Super has pioneered a new form of magic that transcends the "trick." He is the winner of NBC’s TV show "Phenomenon" and was a top finalist on "America’s Got Talent." Tickets $35 to $145. Showtime 8 p.m. 5901 College Rd.

  • February 25 - 26, 2024 Key West
  • Tennessee Williams Theatre: Bobby in the Lobby
  • Website
  • After a four year hiatus, Bobby Nesbitt brings back his acclaimed series “Bobby in the Lobby” to the cabaret, celebrating one of the greatest songwriters of the 20th century, the brilliant Cole Porter. Joining Bobby will be Key West singer Carmen Rodriguez, and from New York, Susan Powell and Richard White. White is renowned for being the voice of Gaston in Disney's Beauty and the Beast. Appearing Sunday and Monday nights at 8 p.m. Tickets $85 to $105. 5901 College Rd.


  • March 02 Key West
  • Coffee Butler Amphitheater: ZZ Top
  • Website
  • Legendary blues rock heavyweights ZZ Top perform at the Coffee Butler Amphitheater for one night. Tickets available online starting at $60. Showtime 7 p.m. 21 Quay Rd.

  • March 05 Key West
  • Tennessee Williams Theatre: Little Women
  • Website
  • Louisa May Alcott’s beloved story of the adventures of the four March sisters is brought to vivid musical life in Little Women. The struggle during the Civil War of these “Little Women” to find their own voices mirrors the growing pains of a young America. With buoyant, joyful melodies, memorable characters, and a big-hearted message, Little Women reminds us that “sometimes when you dream, your dreams come true.” Tickets $45 to $155. Showtime 8 p.m. 5901 College Rd.

  • March 09 Key West
  • Annual Conch Shell Blowing Contest
  • 305-294-9501 Email Website
  • An island tradition, this unique contest celebrates the historic importance of conch in the Keys and features contestants in several age categories attempting to make "music" with fluted conch shells. The contest takes place in the garden of the Oldest House, 322 Duval Street, and is free to participate in and to attend. All ages are invited to compete. Registration begins at 10 a.m., the contest starts at noon.