JANUARY

January 1 

FORT ZACHARY TAYLOR STATE PARK: FIRST DAY HIKE

Join a park ranger for a guided First Day Hike through the park’s Tropical Hammock and Fort Moat trails, observing native vegetation and wildlife. Meet in the Fort parking lot in front of the cannon. The hike begins at 8 a.m. and lasts for one hour. Park entrance fee is required. 601 Howard England Way.

January 3  

STUDIOS OF KEY WEST: STORIES THAT SWING – JAZZ ON THE ROOF WITH LIBBY YORK

A regular at the top venues in New York, Chicago and Paris, celebrated vocalist Libby York presents the best of the Great American Songbook, and a few Bossa Nova gems, with her jazz quartet up on the roof at Hugh’s View. 5:30 p.m.

January 4  

STUDIOS OF KEY WEST: FIRST THURSDAY OPEN HOUSE

During the First Thursday Open House event, the Studios keep the lights on late and throw the doors open to celebrate the newest work in its galleries. Stop in to say hello, relax with a glass of wine on the rooftop terrace, tour the third floor artist studios and see the just-installed exhibitions in the various galleries.

January 4 – 25

THE STUDIOS OF KEY WEST: IT’S IN THE BAG!

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 4 – 25

THE STUDIOS OF KEY WEST: THE STATE OF OUR NATURE

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 4 – 6

WATERFRONT PLAYHOUSE: JOE POSA AS JOAN RIVERS

Having performed alongside Joan Rivers on two separate occasions, Joe Posa was lovingly called by Ms. Rivers, her “favorite Joan Rivers Impersonator.” See his amazing performance at Waterfront Playhouse for three nights only. Showtime 8 p.m. 407 Wall St.

January 5 

TENNESSEE WILLIAMS THEATRE: STARS OF THE NEW YORK CITY BALLET

This is a rare opportunity to see principal dancers from the New York City Ballet performing in Key West. It showcases ballets ranging from the classics to the most contemporary works of today. Show at 8 p.m. 5901 College Rd.

January 5

KEY WEST THEATER: CHUCK CANNON

Chuck Cannon is an American country music singer/songwriter. His compositions include hit singles for Toby Keith and John Michael Montgomery. He appears at Key West Theater as part of the Best of Key West Songrwriters Festival Series. Doors open at 7 p.m., show at 8 p.m. 512 Eaton Street.

January 5

STUDIOS OF KEY WEST: ONE NOBLE JOURNEY

Actor and playwright Mike Wiley performs in the interactive, one-man show as Henry “Box Brown, a black slave who mails himself to freedom in a small crate. Audience members join Wiley on stage, becoming characters helping propel the historic action. Performance in Helmerich Theater at 8 p.m.

January 6 

STUDIOS OF KEY WEST: DAR HE: THE STORY OF EMMETT TILL BY MIKE WILEY

Actor and playwright Mike Wiley, in his second of two one-man performances at Studios of Key West, portrays over 30 different characters in the tragic tale of Emmet Till. This riveting play chronicles the murder, trial and unbelievable confession of the men accused of Emmett Till’s lynching in 1955 Mississippi.  Showtime at 8 p.m. 533 Eaton St.

January 6 

POLE VAULT IN PARADISE COMPETITION

Pole Vault in Paradise brings together pole vaulters of all ages to compete alongside pole vaulting elite athletes. Sponsored by the nonprofit Key West Track & Field Club, the event is staged at Key West High School’s track at The Backyard sports complex, 2100 Flagler Ave. The first flight of pole vaulters starts at 9 a.m. and continues throughout the day. Viewing is free.

January 7 

THE STUDIOS OF KEY WEST: GETTING STARTED WITH ENCAUSTICS

Transform your work with the luminosity of encaustics, also known as hot wax painting. This workshop offers tips for clarifying your idea, how-to’s for prepping the wax and surface, and tips for color, texture and embellishment possibilities. A brief slideshow of encaustics artwork will help inspire you and plan your steps to create. Class leader Cricket Desmarais is a local visual and performing artist who has taught workshops to all levels and ages. 10 a.m. to 2 p.m. in the Kat in the Hat Classroom. 533 Eaton St.

January 9 

TARPON/ALL THAT IS SACRED DOUBLE FEATURE WITH Q & A

The iconic film 1974 documentary Tarpon, which chronicled Key West as a bohemian sportsman’s paradise on the verge of profound change, has been re-imagined into a new short film (with some old footage) called All That is Sacred. Captain Will Benson from the Lower Keys Guides Association and Arlo Haskell from Key West Literary Seminar will discuss the original iconic film and it’s impact that continues to inspire efforts to protect the natural beauty and cultural heritage of the Florida Keys. Showtime 6:30 p.m. 416 Eaton St.

January 9 – 10

THE STUDIOS OF KEY WEST: DAVID WILCOX IN CONCERT

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. 533 Eaton St.

January 10 – 20

FRINGE THEATER: 5 LESBIANS EATING A QUICHE

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.  Showtime 7 p.m. at the Armory, 600 White St.

January 11 – 14

KEY WEST KINGFISH MAYHEM

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

KEY WEST LITERARY SEMINAR: FLORIDA – THE STATE WE’RE IN

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

KEY WEST HOME TOURS

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.

Jan 13  Marathon

PAWS FOR A CAUSE DOG WALK ON THE OLD SEVEN MILE BRIDGE

Enjoy a lovely walk with your dog on the iconic Old Seven Mile bridge to Pigeon Key to support the Domestic Abuse Shelter of Monroe County. A light breakfast will be served on Pigeon Key, then take a leisurely stroll back. Every walker that raises donations of $100 or more will have the $25 registration fee waived. The person that collects the most money will win a great prize. If you don’t have a dog, you can borrow one from the SPCA. Expect to see turtles, manatee, dolphins or rays on the walk. Registration 8:30 a.m., walk at 9 a.m.

January 13 

THE STUDIOS OF KEY WEST: ONE MUSIC FAMILY

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.

January 13 – 14

18TH ANNUAL FLORIDA KEYS SEAFOOD FESTIVAL

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  

SHERIFF’S ANIMAL FARM OPEN HOUSE

Visit the animals at the farm, including miniature horses, a steer, pigs, goats, bunnies, alligators, tropical birds, kinkajous, a capybara, lemur, alpaca, skunk, prairie dog, tortoises and turtles, snakes and many more. It is free of charge, but donations are welcomed because that is how the farm is sustained. The farm is located at 5525 College Rd. on Stock Island at the Sheriff’s Office Headquarters complex. The family-friendly Sheriff’s Animal Farm is open 1 – 3 p.m the second and fourth Sundays of the month.

January 14

26TH ANNUAL KEY WEST HALF MARATHON & RUNFEST

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 15 – 19

THE SOUTHERNMOST REGATTA

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 17  Islamorada

HISTORY OF DIVING MUSEUM: IMMERSE YOURSELF – ICONIC REEF GUARDIANS  

Leaders of the Florida Keys National Marine Sanctuary’s Iconic Reef Guardians Program lead a discussion on how scuba divers and snorkelers can be empowered to support coral restoration and become stewards of the sanctuary’s Mission: Iconic Reef sites. Register online for either the 7 p.m. in-person presentation at the museum or to join virtually. Prior to the presentation, there is to be an opening ceremony for the museum’s new “Dive Into Art: Coral Creations” exhibit. The museum is located at mile marker 82.9 bayside.

January 17 – 20

ROKISLAND FEST

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

RED BARN THEATRE: THIS ONE’S FOR THE GIRLS – THE WOMEN OF COUNTRY MUSIC

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. Showtime 8 p.m. 319 Duval Street.

January 18 

KEY WEST ART & HISTORICAL SOCIETY: HAPPY HOUR WITH THE HISTORIAN

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.

Jan 19 Marathon 

CURRY HAMMOCK STATE PARK: STARRY STARRY NIGHT

Join the Florida Keys Astronomy Club for a magical evening under the stars. The event begins at 5:30 p.m. as the light fades. Please arrive early. The Curry Conservation Cart will roll out with star-themed activities before the program begins. Bring your own chairs, snacks and bug spray. The park is located at mile marker 56.2 oceanside on Crawl Key.

 Jan 19 – 21  Islamorada

ISLAND BOAT SHOW

Island Boat Show features the newest of top boat brands from dealers around South Florida. You’ll also find plenty of boating accessories, fun merchandise, beautiful art, good food, fishing seminars and a silent auction. Proceeds support higher education scholarships for high school students. 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. on the grounds of Island Community Church, mile marker 83.4 bayside.

January 20

SOUTH FLORIDA SYMPHONY: BRAHMS, BACH, MONTGOMERY & PRICE

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. Tennessee Williams Theatre, 5901 College Rd. Curtain time is 7:30 p.m.

January 21 

TENNESSEE WILLIAMS THEATRE: PARADISE BIG BAND

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.  Showtime 8 p.m. 5901 College Rd.

January 22 – 29

KELLY MCGILLIS CLASSIC

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

KEY WEST FOOD & WINE FESTIVAL

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

MILE 0 FEST

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

TENNESSEE WILLIAMS THEATRE: THE MIDTOWN MEN

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. Showtime 8 p.m. 5901 College Rd.

January 26

TENNESSEE WILLIAMS THEATRE: PUPPY PALS, LIVE!

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.  Showtime 7 p.m. 5901 College Rd.

January 28 

SHERIFF’S ANIMAL FARM OPEN HOUSE

Visit the animals at the farm, including miniature horses, a steer, pigs, goats, bunnies, alligators, tropical birds, kinkajous, a capybara, lemur, alpaca, skunk, prairie dog, tortoises and turtles, snakes and many more. It is free of charge, but donations are welcomed because that is how the farm is sustained. The farm is located at 5525 College Rd. on Stock Island at the Sheriff’s Office Headquarters complex. The family-friendly Sheriff’s Animal Farm is open 1 – 3 p.m the second and fourth Sundays of the month.

January 29 

TENNESSEE WILLIAMS THEATRE: ANN FRANK, WORDS FROM THE SHADOWS

The Imperfect Dancers Company presents this inspirational tribute to a young woman’s life and her spiritual strength during one of the darkest moments in the 20th century. Showtime 8 p.m. 5901 College Rd.

 Jan 30 – Feb 3

KEY WESTERN FEST

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.

FEBRUARY

 Feb 2 – 4  Islamorada 

WOMEN’S SAILFISH TOURNAMENT

This challenge has female anglers facing off in Islamorada against the famous tail-dancers for trophies and prizes. Details to come soon.

Feb 2 Marathon 

CRANE POINT HAMMOCK: SIP & SLEUTH

You’re invited to spend an evening solving a mysterious crime while sipping on your beverage of choice. The fun begins at 7 p.m., presented by Keys Mystery Theatre. Tickets are available at the Crane Point gift shop. 5550 Overseas Highway.

Feb 8 – 10

CUDA BOWL

The toothy barracuda are prey for competitors in this annual challenge. The all-release flats tournament got its name because it’s scheduled each year just before the Super Bowl NFL football championship. The event is headquartered at South of the Seven Restaurant on Sugarloaf Key, mile marker 17. Prizes are awarded to the top angler and guide in spin and fly divisions. Top scoring female and junior anglers are also recognized.

February 12 

COFFEE BUTLER AMPHITHEATER: WILLIE NELSON

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

THE STUDIOS OF KEY WEST: RODNEY CROWELL IN CONCERT

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. 533 Eaton St.

February 14

WESLEY HOUSE FAMILY SERVICES VALENTINE’S DAY GALA

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 

TENNESSEE WILLIAMS THEATRE: A STRING QUARTET PLAYS LOVE SONGS

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

PRESIDENTIAL FAMILIES WEEKEND

The Key West Harry S. Truman Foundation, in partnership with The Society of Presidential Descendants, presents a series of special events Presidents’ Day Weekend at the Harry S. Truman Little White House. On 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. 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

KEY WEST HOME TOURS

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.  Addresses of featured homes are to be provided when tickets are purchased.

February 16 

TENNESSEE WILLIAMS THEATRE: DRUM TAO

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.  Showtime 8 p.m. 5901 College Rd.

 Feb 17  Islamorada  

POPS IN THE PARK: WHERE THE WILD THINGS ARE

Florida Keys Community Concert Band performs animal-themed music beginning at 4 p.m. with a free performance titled “Where the Wild Things Are.” There will be special treats and activities for dogs and families in attendance including animal balloons and a pet parade, along with adoptable puppies. Founders Park, mile marker 87 bayside. Bring chairs and blankets for seating.

 Feb 17  The Lower Keys

8TH ANNUAL RUN WITH DEER 5K RUN/WALK

The Florida Keys Wildlife Society’s Run With Deer 5k Run/Walk takes place Sat., Feb. 17 at 8 a.m. within the Key Deer National Wildlife Refuge. Stay tuned for details and registration information.

February 22 – 23

FRINGE THEATER: KEY WEST CHARACTERS – TRUE STORIES

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.  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

KEY WEST ART & CRAFT FESTIVAL

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  

TENNESSEE WILLIAMS THEATRE: MIKE SUPER, ILLUSIONIST

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.”  Showtime 8 p.m. 5901 College Rd.

Feb 24 – 25 Islamorada  

GIGANTIC NAUTICAL MARKET

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.

February 25 – 26

TENNESSEE WILLIAMS THEATRE: BOBBY IN THE LOBBY

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. 5901 College Rd.

MARCH

March 1  

SOUTH FLORIDA SYMPHONY: MASTERWORKS III – BEETHOVEN’S NINTH & GREAT OPERA FINALES

Experience the sheer emotional power of Beethoven’s Ninth plus some of the greatest Opera finales of all time including Carmen, La Boheme and more, featuring spectacular vocal soloists along with the South Florida Symphony Chorus. Tennessee Williams Theatre, 5901 College Rd. Curtain time 7:30 p.m.

March 2  

COFFEE BUTLER AMPHITHEATER: ZZ TOP

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.

 Mar 2  Key Largo

CORAL RESTORATION FOUNDATION: RAISE THE REEF

Join Coral Restoration Foundation at Ocean Reef Club for a dazzling evening dedicated to saving the Keys’ precious coral reefs. Attendees enjoy craft cocktails, silent and live auctions, a sustainably-sourced gourmet dinner and a keynote presentation by underwater filmmaker and marine scientist Dr. Shireen Rahimi. Raise the Reef event guests also have the opportunity to book a room to stay at the exclusive Ocean Reef Club. 6 to 10 p.m. 201 Ocean Reef Drive.

 March 5  

TENNESSEE WILLIAMS THEATRE: LITTLE WOMEN

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.”  Showtime 8 p.m. 5901 College Rd.

 Mar 5 –  9  Key Largo  Fishing

JIMMY JOHNSON’S QUEST FOR THE RING CHAMPIONSHIP FISHING WEEK

Hosted by coach Jimmy Johnson, this prestigious event includes the Quest for the Ring Billfish Championship with a guaranteed 7-figure purse. All anglers on the winning boat receive authentic, custom-designed Jimmy Johnson championship rings. Or, anglers can enter the JJ Sportfish Tournament for top cash prizes. Participants fish in 100 miles of water from Key Largo to Palm Beach.

March 9

ANNUAL CONCH SHELL BLOWING CONTEST

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.

 Mar 9 – 10  Marathon  

MARATHON SEAFOOD FESTIVAL

The Marathon Seafood Festival is the premier event for delicious fresh seafood and entertainment in the Florida Keys. There is to be live music throughout the festival weekend, games for children and adults, raffle giveaways, and over 200 vendors selling jewelry, clothing, art, boats and more. $5 per person, per day. Kids 12 and under free with paying adult. On Sunday, both active and retired military and law enforcement personnel are free. The festival takes place at Marathon Community Park, 200 36th Street oceanside. Additional parking available directly across U.S. 1 at Stanley Switlick Elementary.

March 10 

FOREIGNER AT COFFEE BUTLER AMPHITHEATER

Foreigner’s Farewell Tour stops in Key West on Sun., March 10th for a performance at Coffee Butler Amphitheater. The group is to perform greatest hits, like “Juke Box Hero,” “Cold As Ice,” and “Hot Blooded.” Doors open at 5:30 p.m. Show starts at 7 p.m. 21 Quay Rd.

March 11 – 14

MARCH MERKIN INVITATIONAL PERMIT TOURNAMENT

This charity flats-and-fly-only invitational tournament challenges anglers to catch and release silvery permit to vie for elite titles. The event is held at Oceans Edge Resort & Marina in Key West.

March 11

TENNESSEE WILLIAMS THEATRE: JILLIAN TODD – A CELEBRATION OF THE MUSIC OF JONI MITCHELL

This special evening in the cabaret promises to captivate audiences with soul-stirring renditions of Joni Mitchell’s most beloved songs, including A Case of You and Big Yellow Taxi. Renowned singer and guitarist Jillian Todd headlines the event with her unique talent and heartfelt interpretations. Showtime 8 p.m. 5901 College Rd.

March 12

KEY WEST THEATER: DAVE MASON

Dave Mason, legendary guitarist and founding member of Traffic, plays solo March 12 at 8 p.m. Limited tickets available. 512 Eaton St.

March 13 – 23

FRINGE THEATER: THE LAST 5 YEARS

A poignant and devastatingly honest look at love and loss between two artists whose first date and last goodbye take place over five years. The musical’s innovative structure takes us through their story from start to finish (and finish to start). This show has strong language and adult themes. Showtime is 7 p.m. at the Armory, 600 White St.

March 15 – 16

KEY WEST HOME TOURS

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.  Addresses of featured homes are to be provided when tickets are purchased.

March 15 

COFFEE BUTLER AMPHITHEATER: TEMPTATIONS & THE FOUR TOPS

The Temptations and The Four Tops have cemented their places in music history as pioneers of the R&B genre. See these icons of the American music scene in Key West on March 15. Showtime 7 p.m. 21 Quay Rd.

March 16 

THE STUDIOS OF KEY WEST: ARTIST STUDIO TOURS

Hop on a bike or carpool with friends and spend an art-filled afternoon exploring the homes and studios of Key West artists. Produced by The Studios of Key West, the annual Artist Studio Tour takes you on a self-guided journey through the secret lanes and hidden alleys of Old Town. One of the most popular events of the year, the Artist Studio Tours present the island’s art community in a brand new light. Spend an afternoon discovering new artists, peeking into inspiring workspaces, and perhaps finding a unique souvenir or piece of art for your home. 11 a.m. to 3 p.m. Information on locations will be provided to ticket holders.

March 16  

THE MARSHALL TUCKER BAND AT COFFEE BUTLER AMPHITHEATER

The Marshall Tucker Band is to perform at Coffee Butler Amphitheater on Sat., March 16. ‘Can’t You See’ yourself in Key West with The Marshall Tucker Band? Doors open at 5:30 p.m. Show at 7 p.m. 21 Quay Rd.

March 17

WATERFRONT PLAYHOUSE: TENNESSEE WILLIAMS’ TEN BLOCKS ON THE CAMINO REAL

Waterfront Playhouse’s annual celebration of Tennessee Williams – a staged reading of “Ten Blocks on the Camino Real.” Williams described Ten Blocks as a foray into “plastic theatre” that expanded on the “poetic naturalism” of his better-known work of the era. This staged reading is in celebration of the birth of Tennessee Williams. Showtime 8 p.m.  407 Wall Street at Mallory Square.

March 20  

TENNESSEE WILLIAMS THEATRE: NEIL BERG’S 50 YEARS OF ROCK N’ ROLL, PART 4

Neil Berg’s 50 Years of Rock & Roll uses fascinating stories and groundbreaking music, with tributes to such important and iconic rock stars/groups/genres as Chuck Berry, Little Richard, Elvis Presley, Buddy Holly, Bob Dylan, Frankie Valli, The Beatles, Beach Boys, Motown, Aretha Franklin, The Who, Janis Joplin, Woodstock, Simon & Garfunkel, Carole King, Led Zeppelin, Elton John, Stevie Wonder, Billy Joel, Aerosmith, Linda Ronstadt, Bruce Springsteen, Eagles, Fleetwood Mac, Disco, New Wave, and more. Showtime 8 p.m. 5901 College Rd.

March 22 – 24

OLD DOMINION AT COFFEE BUTLER AMPHITHEATER

The Old Dominion quintet brings the “No Bad Vibes” Tour to Key West March 22nd, 23rd and 24th, along with supporting acts Frank Ray, Greylan James & Kassi Ashton. Doors open at 6 p.m. Shows nightly at 7:30 p.m. 21 Quay Rd.

Mar 23 – 24  Islamorada  

ISLAND FEST FEATURING THE TASTE OF ISLAMORADA

This fun annual island festival features a juried art show, a sandcastle building competition, the “What Floats Your Boat” homemade boat race, live music, great food, classic cars and on Sunday, the annual “Taste of Islamorada” restaurant competition. Free entry; onsite parking $5. 10 a.m. to 5 p.m. both days at Founders Park, mile marker 87 bayside.

March 29 

SOUTH FLORIDA SYMPHONY: MASTERWORKS IV – STRAVINSKY, RAVEL, BERNSTEIN, ZWILICH

South Florida Symphony Orchestra transports you to the high-octane spirit of 1940s Times Square in Bernstein’s “Three Dance Episodes” from the hit Broadway musical On the Town, and a visit with Clarinet Concerto, Zwilich’s stirring elegy on 9/11. Then, be seduced at a Spanish tavern during Ravel’s rhythmic Bolero and be spellbound by Stravinsky’s celebrated nod to Russian folklore, the magical Firebird. Tennessee Williams Theatre, 5901 College Rd. 7:30 p.m.

 Mar 30  Islamorada 

POPS IN THE PARK: MARCH MADNESS

Florida Keys Community Concert Band presents “March Madness,” a rousing event featuring games and puzzles for the audience – including a life-size human checkerboard game – punctuated by college fight songs and marches, along with sports and game show themes. Bring chairs and blankets for seating. The free concert starts at 4 p.m. at Founders Park, mile marker 87 bayside

March 31 

WATERFRONT PLAYHOUSE: TRUNK MATERIAL

Enjoy a fabulous musical evening featuring local and out of town talent singing some of their favorite show tunes from their “trunk material.” Showtime 8 p.m.  407 Wall Street at Mallory Square.

APRIL

April 2 

TENNESSEE WILLIAMS THEATRE: DINOSAUR WORLD, LIVE!

Dare to experience the dangers and delights of Dinosaur World, Live! in this “roarsome” interactive show for all the family. Discover a pre-historic world of astonishing (and remarkably life-like) dinosaurs. Meet a host of impressive creatures, including every child’s favourite flesh-eating giant, the Tyrannosaurus Rex, a Triceratops, Giraffatitan, Microraptor and Segnosaurus! A special meet and greet after the show offers all our brave explorers the chance to make a new dinosaur friend. Don’t miss this entertaining and mind-expanding jurassic adventure, live on stage. Showt at 7 p.m. 5901 College Rd.

April 4 – 6

COFFEE BUTLER AMPHITHEATER: LEGENDS OF MUSIC ROW

Legends of Music Row is an extraordinary three night event featuring top songwriting legends in country music hosted by Country Music Hall of Famer and legendary songwriter Dean Dillon. 2024 artists include Jon Pardi, Kip Moore, Ernest, Craig Morgan and many more. There’s an option to add an additional VIP kick-off party on April 3 and other perks including nightly VIP seating and experiences. Individual lawn tickets are available. 21 Quay Rd..

April 6

WESLEY HOUSE FAMILY SERVICES: BLACK TIE BENEFIT

The Black Tie Benefit in Key West raises funds for Wesley House Family Services. Tickets include a welcome champagne cocktail and wine during dinner service, along with music and dancing. 5:30 – 10 p.m., Playa Largo Resort, mile marker 97.4 bayside.

April 6 

PAPIO KINETIC SCULPTURE PARADE

Revel in the family-friendly, art-inspired, human-powered, mobile sculpture and art-bike parade (think art with parts that move) created in honor of the late Florida Keys rebel folk artist Stanley Papio. The parade rolls through Old Town Key West beginning at sunset with the judges’ station in front of Key West Art & Historical Society’s Custom House Museum.

Apr 13  Marathon

SEVEN MILE BRIDGE RUN

The 43rd annual Seven Mile Bridge Run takes place Saturday, April 13. Motorists need to be aware that the bridge will close in both directions from 6 a.m. to 9 a..m. Saturday morning. This year the race starts at 6:45 a.m. Law enforcement will open the bridge to traffic promptly at 9 a.m. The race is a bucket list adventure for the field of 1,500 runners who participate.

April 17 – 27

FRINGE THEATER: DEATH AND THE MAIDEN

A white-knuckle thriller and riveting tug-of-war. Who do you believe – your deeply troubled spouse, or your new persuasive friend? Winner of the 1992 Olivier Award for Best New Play. 7 p.m. at the Armory, 600 White St.

 Apr 18 – 20  Marathon 

MARATHON PREMIERE SAILFISH TOURNAMENT

A boat tournament with a release format, the challenge benefits Mission Fishin’, a South Florida nonprofit that helps fund marine adventures for foster children, kids with special needs, and their families. Prizes are to be awarded to the top three boat teams and top male, female and junior anglers among others. Tickets available for non-anglers to attend the awards banquet and fundraising auction, Saturday, April 20th, 6:30 to 9 p.m. at Florida Keys Aquarium Encounters, mile marker 53 bayside.

April 19 – 24

42ND ANNUAL CONCH REPUBLIC DAYS

Fans and friends of the Florida Keys’ Conch Republic can celebrate the irreverent “nation’s” 42nd birthday with activities including a tall ship pirate adventure, traditional shrimp boil, sunset boat parade, tour of the USCGC Ingham floating maritime museum, reenactment of the Great Sea Battle of the Conch Republic, performances of “Conch Republic — The Musical,” the World’s Longest Parade, Drag Races on Duval Street and more. The annual Conch Republic Independence Celebration commemorates the Keys’ symbolic 1982 secession from the United States and reinvention as the eccentric republic.

April 25

TENNESSEE WILLIAMS THEATRE: BALLETS TROCKADERO DE MONTE CARLO

The world-renowned Ballets Trockadero de Monte Carlo visits Key West with its troupe of male dancers to present a brilliant combination of skillful ballet movements and hilarious parodies of classic ballets such as Swan Lake. Founded in New York in 1974, the company, affectionately known as the Trocks, began by performing late-night in Broadway lofts to small audiences who appreciated the ensemble’s iconoclastic humour. In the 50 years since, the company has grown to appeal to an ever-growing audience who flock to theatres around the world each season to see these prima ballerinas perform.  Show at 8 p.m. 5901 College Rd.

Apr 27  Islamorada 

POPS IN THE PARK: SCI-FI SERENADE

The free Florida Keys Community Concert Band performance on Sat. April 27 is themed: “Sci-Fi Serenade.” The program includes selections from “Music of the Spheres” along with space movie music. Come dressed to impress in your sci-fi best for an out-of-this-world costume contest.Bring chairs and blankets for seating.

April 28

COFFEE BUTLER AMPHITHEATER: THE PRICE IS RIGHT LIVE

The Price Is Right Live is the hit interactive stage show that gives eligible individuals the chance to hear their names called and “Come On Down” to win. Prizes may include appliances, vacations and possibly a new car! Play classic games just like on television’s longest running and most popular gameshow…from Plinko to Cliffhangers to The Big Wheel and even the fabulous Showcase. Playing to near sold-out audiences for more than 20 years, the Price Is Right Live has entertained millions of guests and given away more than 15 million dollars in cash and prizes. Showtime 8 p.m. 21 Quay Rd.

MAY

May 1 – 5

28TH ANNUAL KEY WEST SONGWRITERS FESTIVAL

The Key West Songwriters Festival is the largest festival of its kind in the world. It revolves around five days and nights where live music bliss introduces crowds to the faces, voices and stories behind the songs. Performances take place at numerous theaters, bars and event spaces around Key West. Save the date and watch for the full schedule of performance to be posted closer to the 2024 event on the festival, keywestsongwritersfestival.com.

May 2

COFFEE BUTLER AMPHITHEATER: COLE SWINDELL

Key West Songwriters Festival presents Cole Swindell in concert May 2. Doors open 5:30 p.m.; Showtime 7 p.m.  21 Quay Rd.

May 12 

TENNESSEE WILLIAMS THEATRE: ONE NIGHT OF QUEEN

For over 20 years Gary Mullen and The Works have been performing their world-renowned “One Night of Queen” live concert. Gary Mullen & The Works will have you dancing in the aisles during their show, while the band pays tribute to the stage theatrics, showmanship, and music of Rock & Roll Hall of Fame inductees: Queen.  Show at 8 p.m. 5901 College Rd.

JUNE

June 5 – 9

KEY WEST PRIDE

Celebrate PRIDE on the tropical island of Key West that is legendary for its laid-back style and its open and accepting atmosphere. Whether you’re looking to party with friends, travel with family, or to get lost in the magic of the southernmost city, rediscover Key West and discover how the island has created one of the most integrated and unique communities in the world. Show us your pride, we will show you our Key West Pride!

 Jun 7 – 9 The Lower Keys  

LOWER KEYS CHAMBER OF COMMERCE DOPHIN TOURNAMENT

The Lower Keys Chamber of Commerce presents the 31st annual event where anglers contend for over $35,000 in cash prizes and awards. A special cash prize of $20,000 is awarded for the largest dolphin over 50 pounds — this prize is available only to the anglers on the first 50 boats registered for the tournament. Additional prizes await winners in open, ladies and youth divisions.

Jun 8 

CFK SWIM AROUND KEY WEST

Embark on an adventurous competitive swim – a 12.5 loop around the island. The pristine waters around Key West give swimmers great views of both the land and underwater life. Compete in different categories including solo swimmer, solo swimmers with fins, solo swimmers using a mermaid tail or a monofin, or gather your friends and compete in the relay category of 2-person, 3-person, 4-person, 5-person or 6-person teams. Not interested in the full island swim? Try some of the smaller races offered, a 6.1-mile swim, a 2-mile swim, a 1-mile swim or an 800-yard swim. Swims begin and end at Higgs Beach, 1000 Atlantic Boulevard.

June 15 

HARRY S. TRUMAN LITTLE WHITE HOUSE: TRUMAN’S TROPICAL FRUIT FESTIVAL

Can you tell the difference between a haden and a kent mango? At the Tropical Fruit Festival, you’ll have the chance to taste all types of mangoes and other tropical fruits, sip tasty cocktails, watch cooking demos, purchase tropical trees, shop with local vendors and more. 9 a.m. to noon. 111 Front St.

June 27 – 30

SEVENTH ANNUAL MANGO FEST KEY WEST

Experience all things mango through culinary treats, education and demonstrations during this celebration of the Keys’ sweet indigenous fruit and its heritage. Stroll around the Mango Mania vendor village at Bayview Park–1320 Truman Ave., enjoy mouthwatering mango-themed specialties during special dining events, attend lectures and more. The festival is presented by the Key West Police Athletic League and supports its local youth programs.

JULY

July 3 – 7

KEY WEST KEY LIME FESTIVAL

Key West’s annual Key Lime Festival celebrates the world’s most sensational citrus with a bountiful array of festivities across the island where Key lime pie was conceived. Over five days, lovers of the lime can indulge in a full menu of activities including a Key lime pie drop competition from the top of the Key West Lighthouse; a Key lime cocktail sip and stroll, Key lime brunches and dinners, and of course, the world famous Key lime pie eating championship at 1:30 p.m. on July 4th at Southernmost Beach Cafe at 1405 Duval St.

 Jul 12 – 13  The Lower Keys 

40TH ANNUAL UNDERWATER MUSIC FESTIVAL

Celebrate the 40th anniversary of the Underwater Music Festival with a free welcome event and tour Friday evening at Mote Marine, 24244 Overseas Highway on Summerland Key to learn about coral restoration efforts. Then on Saturday, join the underwater “musicians” in costume or just come as you are to dive and snorkel Looe Key Reef, an area of the Florida Keys National Marine Sanctuary about 6 miles south of Big Pine Key. Trips are can be booked with area diver operators. Each year, costumed divers pretend to play faux musical instruments in the undersea environment to ocean-themed music piped underwater. Hosted by the Lower Keys Chamber of Commerce and local radio station, U.S. 104.1 FM, the ocean celebration encourages environmentally responsible diving and preservation of the world’s coral reefs, and also offers a bucket-list underwater experience.

Jul 12 – 13  Marathon

FLORIDA KEYS BREWBQ

The fourth annual BrewBQ takes place Friday and Saturday at Marathon Community Park, mile maker 49, featuring mouth watering barbecue and and plenty of craft beer to wash it down. Highlights include the amateur BBQ cooking competition along with vendors, live music, kids’ games and more. Friday from 5 to 9 p.m.; Saturday 11 a.m. to 8 p.m. Sponsored by the Marathon Chamber of Commerce. $5 per person, per day.

July 16 – 21

HEMINGWAY DAYS

Ernest Hemingway look-alikes, writers, anglers, and fans of the late author’s work are to gather in Key West Tuesday through Sunday, July 16-21 for the annual Hemingway Days celebration. The festival honors the legacy of the American literary giant who lived and wrote on the island for most of the 1930s. Events include the legendary Hemingway Look-Alike Contest, the wacky Running of the Bulls on Sat. July 20, presentations, prose and poetry readings, a commemoration of the 125th anniversary of Hemingway’s July 21 birth, a museum exhibit, a 3-day marlin tournament, a 5k run and paddleboard race, a street fair and more.

 Jul 18 – 20  Key West  

HEMINGWAY LOOK ALIKE CONTEST

Dozens of stocky, bearded men resembling Ernest Hemingway are to return to Key West for the annual Hemingway® Look-Alike Contest. Staged at Sloppy Joe’s Bar where it began some 40 years ago, the contest’s preliminary rounds are slated for 6:30 p.m. July 18 and 19. The winner is to be chosen July 20, in a final round starting at 6:30 p.m., from a field of about 24 Hemingway hopefuls.

 Jul 20

HEMINGWAY 5K SUNSET RUN & PADDLEBOARD RACE

The Hemingway 5k Sunset Run & Paddleboard Race is to challenge competitors Saturday, July 20. Registration opens at 3 pm. at Southernmost Beach Cafe, 1405 Duval Street. The paddleboard race starts at 5:30 p.m. from Higgs Beach, 1000 Atlantic Blvd; and the 5k Run/Walk starts at 7:30 p.m. at Southernmost Point. The awards party is from 8 to 10 p.m. at Southernmost Beach Cafe with food and beverage tastings, raffles and entertainment. The athletic challenges are part of Hemingway Days, a six-day commemoration of the life and work of the author who lived and wrote in Key West for most of the 1930s.

AUGUST

SEPTEMBER

September 1

IT’S 5 O’CLOCK IN KEY WEST: A CELEBRATION OF JIMMY BUFFETT

Join the citizens of Key West and fans from around the world to celebrate the life and music of Jimmy Buffett. Within hours of the news of his passing in September 2023, a celebratory Second Line Procession was organized and held on Duval Street. In 2024, the parade will proceed down Duval, ending at Coffee Butler Amphitheater with a concert.

Sep 7  Islamorada

SWIM FOR ALLIGATOR LIGHTHOUSE

Swimmers have up to seven hours to complete the eight-mile roundtrip course out and back around Alligator Reef Lighthouse, ranked as one of the toughest swim challenges in the world. The course features an in-water start and a beach finish, ending shoreside during this tropical open-water swimming event. The competition raises funds for the restoration of the 151-year-old structure, located in the Atlantic Ocean off Islamorada.

OCTOBER

October 18 – 27

KEY WEST FANTASY FEST

“It’s a 90s Neon Cosmic Carnivale” is the official theme for Fantasy Fest 2024–Key West’s annual multi-day costuming extravaganza in paradise. From October 18-27, revelers can explore an array of exciting events, including the world-famous Bud Light Fantasy Fest parade, the all-hands-on-deck Captain Morgan Masquerade March (aka “Locals Parade”), the exuberant Goombay Festival in the streets, Royal Coronation of the 2023 Fantasy Fest King, Queen, plus concerts, theater productions, a “Heroes and Villains” 5K run/walk, the enchanting Key West Pet Masquerade, the 41st annual Headdress Ball pageant, and more.

NOVEMBER

November 3 – 10

RACE WORLD OFFSHORE WORLD CHAMPIONSHIP

Leading American and international powerboat teams compete in high-speed races. On race days, spectators can get an unmatched view from areas at the Truman Waterfront Race Village and adjacent “Outer Mole” pier. Other popular viewing areas include restaurants and bars at harborfront hotels, as well as Key West’s Mallory Square. Both general admission and VIP viewing options available.

DECEMBER

December 1 – 31

KEY WEST HOLIDAY FEST

A merry range of celebrations during Key West’s busy holiday season traditionally includes the Harbor Walk of Lights, Holiday Historic Inn Tours and a lighted boat parade with festively lit vessels and good cheer. Other events include the annual hometown holiday parade, festive island lights tours via the Conch Tour Train and Old Town Trolley, seasonal artisan markets and bazaars, and New Year’s Eve “drops” that spoof New York City’s annual Times Square “ball drop.”

December 4 – 15

NUTCRACKER KEY WEST

Performed every other year, Nutcracker Key West is a sumptuous, artful theatrical experience wrapped as a perfect holiday gift for the Southernmost City, returning December 2024. The Key West production comes complete with chickens, roosters, sea fans, anemones, and yes, even a conch shell. Exact dates are to be determined.

 Dec 6  Islamorada  

ISLAMORADA HOLIDAY FEST

The forecast for Dec. 1 calls for snowballs in Founder’s Park as Snow Mountain returns to the 20th annual Holiday Fest. Kids will need their mittens to play on the icy mound made of 30 tons of snow. The annual holiday tree will be blowing snow from its branches during the celebration. The holiday bazaar is the perfect place to shop for holiday treasures including art, jewelry and unique gift items. Fifty special holiday ornaments crafted by local artists are available through an online auction during the event. Don’t miss Santa’s Sweet Shoppe and the annual Holiday Parade. Festivities run from 4 to 10 p.m. with the parade at 7:30 p.m. MM 87 bayside.

December 4 – 7  Key West

COMEDY KEY WEST: BRENDAN EYRE

Brendan Eyre is one of the country’s top young comedians. His laid back, observational style is a hit with audiences across the country. Showtimes 8:30 p.m. 218 Whitehead St.

 December 5  Key West

SLOPPY JOE’S BAR: END OF PROHIBITION REPEAL PARTY

Party like it’s 1933 at the End of Prohibition Repeal Party! Live entertainment runs all day beginning at 10 a.m. The party really begins in the 5 o’clock hour with the Repeal Party commemorating the historic 5:32 pm. repeal. Costume anti-Prohibition revelers will enjoy swinging bands, costume contests, period cocktails and more. The fun runs through 2 a.m. Find the action and fun at Sloppy Joe’s Bar, 201 Duval Street.

 December 5 – 6  Key West

KEY WEST INTERNATIONAL DANCE CO.: FIESTA DE NAVIDAD TROPICAL

Fiesta de Navidad delivers a festive extravaganza to ignite the holiday spirit. With world-class Latin dance and vibrant costumes, this joyful celebration also offers the opportunity for audience members of all ages to dance on stage with a live band! Performances take place at 8 p.m. at San Carlos Institute, 516 Duval St.

 December 5  Key West

PET PICTURES WITH SANTA

Bring your festively outfitted pets for professional photos with Santa on Friday evening from 6 to 8 p.m. at the Christmas tree at the foot of William Street at Key West Bight Marina, hosted by All Animal Clinic. Photos are $25 each (cash only) with proceeds benefitting the Boys and Girls Club of the Keys.

 December 5 – 15  Key West

NUTCRACKER KEY WEST

Performed every other year, Nutcracker Key West is a sumptuous, artful theatrical experience wrapped as a perfect holiday gift for the Southernmost City, returning December 2024. The Key West production comes complete with chickens, roosters, sea fans, anemones, and yes, even a conch shell. Show dates Dec. 5-8 and 13-15. Showtimes vary. Tennessee Williams Theater, 5901 College Rd.

 December 6  Key West

HOLIDAY HISTORIC INN TOURS: NIGHT #1

In this first of two holiday historic inn tours, explore four beautifully decorated locations and their unique architecture and history from 6 to 8 p.m. Sample sweet and savory holiday treats and libations. Locations are: Hemingway’s Social Club at Papa’s Pilar Distillery, Lighthouse Inn, Wicker Guesthouse, and the Gardens Hotel. The tours are self-guided. $40 tickets available online, but must be picked up after 5:30 p.m. on Dec. 6th at the first location, Hemingway’s Social Club at Papa’s Pilar Distillery, 210 Simonton St. The second inn tour takes place Dec. 13.

 December 6  Key West

COFFEE BUTLER AMPHITHEATER: HOLIDAY VILLAGE & BELIGHTED BIKE RIDE

The Wesley House Family Services Holiday Village is the family-friendly pre-party for the BeLighted Bike Ride, creating an evening of joy, laughter, and holiday magic for all ages, from 5 to 9 p.m. at Coffee Butler Amphitheater, 21 Quay Rd. The village features over 20 community booths offering games and activities, carnival rides, bounce houses, local food trucks, community performances, snowfalls and Santa! The highlight of the evening is the BeLighted Bike Ride that departs from the event at 8 p.m. The luminous parade of holiday cheer on wheels winds through the streets of Key West. Admission to Holiday Village is $20 per person or four tickets for $70. Children age 3 and under enter free.

 December 6  Key West

KEY WEST ART & HISTORICAL SOCIETY: OPENING RECEPTION FOR COLLECTING KEY WEST – THE WORKS OF MARIO SANCHEZ

The Key West Museum of Art & History is pleased to present the opening of the exhibition, “Collecting Key West: The Works of Mario Sanchez” on Friday, December 6. A reception to mark the opening is to take place from 5 to 8 p.m. that evening in the Bryan Gallery, which is free and open to the public. Exploring the crossroads of art and history, this exhibition delves into the legacy of Cuban American folk artist Mario Sanchez (1908 – 2005). Sanchez established himself as the foremost Key West artist in the 1940s, creating hundreds of intricately carved and painted intaglios that portray his birthplace in the first part of the 20th century better than any annals or academic texts. 281 Front St.

 December 6  Key West

KEY WEST THEATER: UNDER THE STREETLAMP

Under the Streetlamp is an electrifying show driven by an inspired catalog of classic Doo Wop, Motown, and Rock n’ Roll hits! Streetlamp has been dazzling audiences across the globe for over a decade. Their five specials airing on PBS have played to more than 300 million viewers and a million people have seen them live. These dynamite Broadway stars are propelled by an ensemble of world-class musicians through a show packed with smooth harmonies, soul-touching music and stories, and thrilling choreography. The audience engagement is palpable, often bringing four generations of music lovers together. Doors at 7 p.m.; show at 8 p.m. 512 Eaton St.

 December 7  Key West

KEY WEST THEATER: THE KINGSTON TRIO

In celebration of 60-plus years of music, the iconic folk group performs their best-loved songs as part of the ‘Keep The Music Playing’ national tour. All three current members, Mike Marvin, Tim Gorelangton and Buddy Woodward, have intrinsic links to the original group: Mike is the “adopted son” of founding member Nick Reynolds, who was also his musical mentor; Tim, a friend of John Stewart since he was in his early twenties, is one of the few musicians outside the Trio who has recorded with Nick Reynolds; and Buddy Woodward, a highly regarded musician who has worked with former Trio member George Grove. Doors 7 p.m.; show 8 p.m. 512 Eaton St.

 December 7  Key West

KEY WEST HOMETOWN HOLIDAY PARADE

Charming holiday spirit abounds in this annual parade in the southernmost city in the continental U.S. Local, hometown flavor prevails with marching bands, school groups, motorized and non-motorized floats and lively community participation. The parade kicks off at 7 p.m. at Truman Avenue and White Street beside Bayview Park and proceeds down Duval Street. Seeing Santa is a highlight for kids.

 December 8  Key West

EATON STREET CHRISTMAS STROLL

Eaton Street becomes a southernmost North Pole Sunday afternoon and evening. Wander the blocks between Whitehead and Simonton, stopping at multiple venues for shopping and special presentations, including United Methodist with a 3:30 p.m. concert, Woman’s Club of Key West, Salt Gallery, an open house at The Studios of Key West, classic cartoons at Tropic Cinema at 6 p.m., a 7 p.m. choral concert at St. Paul’s Episcopal, and more. The event is free but tickets are recommended.

 December 8  Key West

KEY WEST ARTISAN MARKET AT SOUTHERNMOST BEACH RESORT

Join the Key West Artisan Market and the Southernmost Beach Resort for a very special holiday event on the beach. Find some of your favorite local artists with the perfect gifts for everyone on your list along with lots of activities for the kids, great food, tasty treats, fun drinks and even a visit from old St. Nick himself! Live music all day and a fun sand ‘snowman’ building contest. Free to attend from 10 a.m. to 3 p.m. 504 South St.

 December 8  Key West

SHERIFF’S ANIMAL FARM OPEN HOUSE: CHRISTMAS ON THE FARM

Celebrate Christmas at the Monroe County Sheriff’s Animal Farm from 1 to 3 p.m. This will be the only open house during the month of December. Visit with the animals and participate in joyful holiday-themed activities including crafts, music and visits with Santa! Gifts of fresh produce and other items, as well as cash gifts for the animals, are greatly appreciated!

 December 9 – 23 Key West

OLD TOWN TROLLEY: HOLIDAY NIGHTS TOURS

Take the trolley for a tour of the Key West residential neighborhoods known for going all-out with holiday home decorations. Make this your new holiday tradition with friends and family. Narrated tours depart from Mallory Square and last for one hour. Advance tickets are available to book online.

 December 9 – 23  Key West

CONCH TOUR TRAIN’S HOLIDAY SIGHTS & FESTIVE NIGHTS TOURS

The lively holiday Conch Tour Train tours depart from Key West High School, 2100 Flagler Ave., at 6:30, 7, 7:30, 8 and 8:30 p.m. on evenings from Dec. 9 to 10 and 13 to 23. Included are holiday lights glasses as keepsake items. The one-hour tour takes riders past the island’s most elaborately decorated houses, buildings and neighborhoods, with holiday caroling.

 December 10  Key West

LATEDA CHRISTMAS PARTY

All are welcome to attend the annual LaTeDa Christmas Party Dec. 10 from 6 to 9 p.m. For entry, please bring an unwrapped gift for a child in need. Enjoy holiday music by DJ Rude Girl with other special appearances along with a Christmas buffet and drinks. Dress is holiday festive. 1125 Duval St.

 December 10  Key West

FRINGE THEATER: TONY KONRATH’S A CHRISTMAS CAROL

‘Tis the season! It’s a fresh take on the Charles Dickens ghost story of holiday transformation and redemption. Showtimes at 7 p.m. at the Armory, 600 White St.

 December 11  Key West

GAY KEY WEST HOLIDAY LIGHTS TROLLEY TOUR

Slip into your fabulous festive gear and jump aboard this Holiday Lights extravaganza for a dazzling night showcasing the island’s sparkliest displays. Kick things off at Bobby’s Monkey Bar, 900 Simonton St., at 5:30 p.m. with a jingle and mingle before the trolley rolls in at 6:30 p.m. Then it’s a two-hour joyride and a few merry pit stops for cheer-fueling. Bring your favorite holiday goodies to share with our fabulous guests. We’ll wrap up the adventure around 8:30 p.m. back at Bobby’s. Register now so you don’t miss out. After you sign up, we’ll slide into your inbox for payment details.

 December 13 – 14 Key West

PIGEON KEY HOLIDAY SPECTACULAR

The wonderment and excitement of the holiday season takes over Pigeon Key with a festive event that kicks on Friday, Dec. 13 with a VIP viewing of the island in full holiday splendor. On Saturday, the “Polar Express” starts running at 1 p.m. with trips throughout the day and into the evening. Families can spend the entire day on the 5-acre island enjoying marine science activities along with delicious holiday food, drinks, guided tours, activities, holiday-themed movies on the big screen, Santa Claus encounters and snow! Admission $5 for walkers/bikers; ride the Polar Express for $10 if you book in advance or $15 the day of the event.

 December 13  Key West

HOLIDAY HISTORIC INN TOURS: NIGHT #2

In this second of two holiday historic inn tours, explore four beautifully decorated locations from 6 to 8 p.m. while enjoying sweet and savory holiday treats and libation samplings. Locations are: Key West Butterfly Conservatory, The Mansion on the Sea, Island City House and The Mermaid & the Alligator. The tours are self-guided. $40 tickets available online, but must be picked up in person after 5:30 p.m. at the first location – Key West Butterfly Conservatory, 1316 Duval Street.

 December 13 – 28  Key West

WATERFRONT WINTER WONDERLAND

Make your Key West holiday experience even more magical at Waterfront Winter Wonderland at Truman Waterfront Park. Coffee Butler Amphitheater transforms into an amazing winter wonderland, with an ice-skating, rides, games, music, holiday lights, a vendor village with food and local artisans, and more from Dec. 134-23 and 26-28 (closed Christmas Eve and Christmas). 21 Quay Rd. General admission $10, free for children age 5 and under. Additional fees apply for ice skating and rides.

 December 13  Key West

KEY WEST ART & HISTORICAL SOCIETY: HOLIDAY CONCERT & BAZAAR

Join the Key West Art & Historical Society for the 7th Annual Holiday Concert & Bazaar from 5 pm to 9 pm. The event is located on the sweeping historic porch and street in front of the Custom House Museum. The immensely popular celebration will feature some of the Key West’s finest artisans, musicians and choirs, food and libations, and a holiday light show designed by Key West High School’s Conch 5 Studios, which will be projected on the face of the Custom House. There will be plenty of food and festive libations at this event along with excellent holiday shopping. The event is free and open to the public. 281 Front St.

 December 13  Key West

KEY WEST OUTDOOR MOVIES – NIGHTMARE BEFORE CHRISTMAS

Key West Outdoor Movies presents Tim Burton’s The Nightmare Before Christmas, Friday, Dec. 13, at the parade grounds at Fort East Martello, 3501 S. Roosevelt Blvd. The grounds open at 5 p.m. Food and drink will be available for sale by vendors onsite, and there will be free popcorn and activities for all. Bring low chairs or a blanket. The movie starts at dusk.

 December 13  Key West

KEY WEST THEATER: THE MAGIC OF CHRISTMAS

The Magic of Christmas is an adult- and kid-friendly magic show that combines different genres of magic into one fantastic show. Enjoy a complimentary cookie and candy bar along with pictures with Santa by photographer Rob O’Neal. Special appearance by our dancing grinch and some say it even may snow that night. Doors open at 5 p.m.; show at 6 p.m. 512 Eaton St.

 December 14  Key West

SCHOONER WHARF BAR LIGHTED BOAT PARADE

Don’t miss this magical nautical display of holiday lights on board every manner of watercraft in Key West Harbor. The judges stand is located at Schooner Wharf, 202 William St. Viewing is available from all along the Harbor Walk. The parade starts at 8 p.m.

 December 14  Key West

‘A POSITIVE STEP’ 5K RUDOLPH RED NOSE RUN

Don your festive holiday jammies and join in the 16th ‘A Positive Step’ 5k Rudolph Red Nose Run, starting and ending at the Southernmost Beach Café, 1405 Duval Street. Race day check-in starts at 7 a.m. with start time at 8 a.m. Prizes are awarded for most festive and most unusual PJ’s. After the race, enjoy refreshments and a fabulous silent auction to benefit A Positive Step of Monroe County, a non-profit serving at-risk kids and their families.

 December 15  Key West

SNOWY DAYS CHILDREN’S CONCERT AT KEY WEST BOTANICAL GARDEN

Snowy Days, the Key West Tropical Forest & Botanical Garden’s annual children’s winter concert, features Key West vocalist, Belle Jampol performing favorite holiday tunes for children. The event opens at 1 p.m. and the concert starts at 1:30 p.m., followed by snow cones (while they last) and delightful holiday arts and crafts, face painting and special treats. Tickets $5 per child at the door with a maximum cost of $10 per family.

 December 15  Key West

KEY WEST ARTISAN MARKET: FILL THE PANTRY EDITION

Stock your pantry and fridge with fresh produce, exotic fruits, artisan cheeses, local seafood, honey, pickles, nuts and so much more. Enjoy bloody’s, mimosas along with a full bar, coffee, smoothies, natural juices and cut fruit, multiple food trucks and stalls offering eat-here or take-away for snacking or a delicious meal. Shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers. Listen to awesome local musicians and give canned good or donations to our featured charity, the SOS Foundation, that feeds Key West’s underprivileged children. 10 a.m. to 2 p.m., 1801 White St. in Indigenous Park.

 December 18  Key West

FRINGE THEATER’S HOLIDAY TRAIN RIDE

Don’t miss this crowd favorite fundraiser for Fringe Theater. Check-in at 7 p.m. at the beautiful Gardens Hotel, 526 Angela St., and enjoy a tasty beverage at the cash bar while you catch up with your Fringe friends and enjoy the live holiday music. Then at 8 p.m., it’s “All Aboard” our Holiday Train for a festive ride about town to see the holiday lights of Key West. Pickup and return at the Gardens Hotel. Tickets $60.

 December 18  Key West

KEY WEST ART & HISTORICAL SOCIETY HISTORIC SEAPORT SAIL: PLANT A MILLION CORALS PROJECT

Enjoy a 2-hour Historic Harbor Tour with Plant A Million Coral Project’s Dee Dee Vaughan on the S/V Argo Navis, talking about the Project to Restore Florida Keys’ Coral Reef. The morning seafaring excursion aboard luxury catamaran SV Argo Navis departs from the dock at 0 Margaret Street at 10 a.m. and returns at 12 p.m. Passengers will enjoy Bloody Marys, mimosas or non-alcoholic beverages along with lite breakfast fare as Vaughan explains the Plant A Million Coral’s focus on active reef restoration and the transfer of coral restoration technology. Book tickets online in advance.

 December 18 – 21  Key West

COMEDY KEY WEST: JIM FLORENTINE

For nearly 25 years Jim Florentine has been making audiences around the world laugh across nearly every type of media. Jim has recorded six stand-up comedy albums and shot four full-length specials. Showtimes 8:30 p.m. 218 Whitehead St.

 December 19  Key West

WALK ON WHITE THIRD THURSDAY ART WALK

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. In December, The KWHS marching band will parade down White Street and perform at various locations along the way. City Hall and the NOAA National Weather Station will also participate.

 December 19  Key West

KEY WEST ART & HISTORICAL SOCIETY DISTINGUISHED SPEAKER SERIES: STORMS, SHIPWRECKS & SAINTS’ NAMES

This talk focuses on the dangers associated with early Caribbean and Gulf travel in the first generations of Spanish colonialism. The Florida Keys were a late and important, but also particularly treacherous, final leg of a roundtrip journey from Spain, through the Caribbean, and back to Spain. Dr. Kevin Kokomoor talks on the subject and brings to light discoveries covered in his recent book, “La Florida: Catholics, Conquistadores and other American Origin Stories.” 6 to 7 p.m. at Tropic Cinema, 416 Eaton St.

 December 21  Key West

TROPIC CINEMA: MOVIES UNDER THE STARS – ELF

Don’t miss the monthly free Movies Under the Stars screening – this month, the movie is Elf! 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 6 p.m. 416 Eaton St.

 December 21  Key West

RUNNING OF THE ELVES 5K RUN/WALK & JINGLE BELL MILE

Put on your best festive holiday costume and run, jog, stroll or jingle all the way to the finish line, where organizers promise to make it snow! This first annual fun run benefits Reef Relief. The run starts at 5 p.m. at Coffee Butler Amphitheater. Your run registration comes with a free ticket to Waterfront Winter Wonderland at the amphitheater along with an elf T-shirt, holiday race medal, Christmas cookies, candy canes and a photo with holiday characters including Buddy the Elf!

 December 22  Key West

KEY WEST ARTISAN MARKET: SHOP LOCAL EDITION

This week’s market will be stocked with Keys-made items perfect for gift giving this holiday season. Enjoy bloody’s, mimosas along with a full bar, coffee, smoothies, natural juices and cut fruit, multiple food trucks and stalls offering eat-here or take-away for snacking or a delicious meal. Shop a curated outdoor market offering fine crafts, art and jewelry. Stock your pantry and fridge with fresh produce, artisan cheeses, local seafood, honey, pickles and so much more. Listen to awesome local musicians doing your favorite Christmas standards, and get photos with Santa! 10 a.m. to 2 p.m. in Indigenous Park, 1801 White St.

 December 22  Key West

THE GARDENS HOTEL: HOLIDAY JAZZ IN THE GARDENS

Find festive outdoor jazz in The Gardens Hotel’s famous outdoor garden, with a full cash bar on site and a 20% Christmas discount on bottled wine and bubbly. 5 to 7:00 p.m. 526 Angela Street.

 December 24  Key West

OLD ISLAND RESTORATION FOUNDATION: NOCHE BUENA

This Christmas Eve event is a celebration of Key West Cuban heritage. Enjoy a traditional succulent roast pig dinner loaded with sides and topped off with El Mocho’s homemade flan. $50 adults, $15 age 12 and under. Call for information and tickets, 305-294-9501 or visit the website.

 December 29  Key West

KEY WEST LIGHTING OF THE MENORAH

The City of Key West’s annual Lighting of the Menorah ceremony takes place at Bayview Park Sunday, Dec. 29 from 5 to 7 p.m. 1320 Truman Avenue.

 December 30  Key West

SUNSET GREEN LAWN: EARLY NEW YEAR’S EVE CELEBRATION

This event is the perfect way to kick your New Year’s celebrations a day early. Come to the Sunset Green Lawn for a FREE night of music and family-friendly fun to start the countdown to 2025 with the talented Mike Stack and friends! Featuring Mike Stack, The Brickfinders, D-Lew, Sharese, Josh Kiser, Jockey Jord and other special musical guests. The show is to be followed by a fireworks display! Gates open at 6 p.m. with music starting at 6:30 p.m.

 December 31  Key West

HEMINGWAY’S DISTILLERY: NEW YEAR’S EVE COCKTAIL CLASS

Step back in time to the 40s where adventures ran high, cocktails lit up the night and men and women were all about fashion, fun and enjoying lots of rum. Participants will be instructed by a Hemingway’s Distillery Cocktail Specialist on how to make 2 Papa’s Pilar signature cocktails. Each guest has their own station with tools and all the ingredients needed to create these fabulous cocktails, and you get to enjoy what you create. Come dressed in Casablanca-themed attire or Key West cocktail casual. 6:30-9:30 p.m. 201 Simonton St. Tickets available online

 December 31  Key West

SCHOONER WHARF BAR: NEW YEAR’S EVE LOWERING OF THE PIRATE WENCH

Celebrate the New Year in true Schooner Wharf Bar style with the annual Lowering of the pirate wench down the mast of the Schooner America 2.0 at midnight. Enjoy live music through the afternoon and evening, with cannon’s firing, party favors and fun at midnight. 202 William St.

 December 31  Key West

NEW YEAR’S EVE RED SHOE DROP

Witness Key West’s iconic Red Shoe Drop at the Bourbon Street Pub, 724 Duval St. Free to watch from Duval Street; VIP options are to be available for balcony seating. Live entertainment in the street starts at 9 p.m. with the shoe drop at midnight.

 December 31  Key West

NEW YEAR’S EVE CONCH SHELL DROP AT SLOPPY JOE’S

The arrival of 2025 is to be heralded on Key West’s Duval Street with the “drop” of a gigantic manmade conch shell, the symbol of the Florida Keys, to the flat roof of Sloppy Joe’s Bar, 201 Duval. Spectators gather on Duval for the annual gala, emceed by a rooftop host and featuring dancing in the street and a countdown to midnight recorded on a huge clock. Customers inside the bar may view the dropping of the conch shell on Sloppy-Tron.

 December 31  Key West

NEW YEAR’S EVE GATSBY GALA AT FIRST FLIGHT ISLAND RESTAURANT & BREWERY

Dress to impress in your Gatsby-era best for First Flight Island Restaurant & Brewery’s New Year’s Eve gala. Enjoy live music, DJ tunes and the Plane Drop at midnight. Heavy hors d’oeuvres, chef-manned food stations and an open bar. Purchase tickets in advance to ensure entry.

Happy New Year 2024!

Check in for the 2025 Schedule of Events developing