Events & Festivals
Oct 20, 2023 – Oct 29, 2023
Key West Fantasy Fest
This outrageous 10-day costuming and masking celebration features dozens of masquerade competitions, themed parties and other exuberant events. In recognition of the 200-year anniversary of Monroe County and Key West’s first Naval base, the 2022 theme is ‘“Uniforms & Unicorns — 200 Years of Sailing into Fantasy.” Check the website for the full schedule and more details.
Dec 31, 2023
New Year’s Celebration at Schooner Wharf
The Unique Schooner Wharf Bar’s Seaport Tradition – Lowering of the Pirate Wench at Midnight. Party starts early in the day with 3 Local and National Acts – Party Favors – Champagne & Fun
2024 Events
Jan 4, 2024 – Jan 6, 2024
Joe Posa as Joan Rivers
https://www.waterfrontplayhouse.org/buy-tickets/
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.
Jan 6, 2024
Pole Vault in Paradise Competition
https://kwtfc.org/pole-vault-in-paradise/
Pole Vault in Paradise brings together pole vaulters of all ages to compete alongside some of the best pole vaulting elites from around the country. Sponsored by the nonprofit Key West Track & Field Club, the event is to be staged at Key West High School’s track at The Backyard sports complex, 2100 Flagler Ave. The main event is Saturday. The first flight of pole vaulters starts at 9 a.m.
Jan 11, 2024 – Jan 14, 2024
Key West Literary Seminar: Florida – The State We’re In
https://www.kwls.org/seminar/
Readers and writers gather together every January for this focused and festive four-day literary celebration. For “Florida: The State We’re In,” you’ll find a cast of novelists, poets, historians, humorists, and cultural critics who know the Sunshine State better than anybody. During this literary exploration of Florida, we may not solve all the problems of this crazy place, but we’ll sure have a good time talking about it. 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.
Jan 15, 2024 – Jan 19, 2024
The Southernmost Regatta
https://www.thesouthernmostregatta.com/
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 16, 2024 – Jan 20, 2024
RokIsland Fest 2023
https://www.rokislandfest.com/
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 five 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.
Jan 23, 2024 – Jan 28, 2024
Key West Food & Wine Festival
https://keywestfoodandwinefestival.com/
The festival include over 20 unique events 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 Ole Espana, celebrating the wine and culture of Spain and its impact on Key West. Key West, or Cayo Hueso (Island of Bones) was discovered by Ponce de Leon, named Las Martines and claimed by Spain in 1513. In 1815 Don Juan de Estrada granted Key West to Juan Pablo Salas for meritorious service to the crown.
Jan 23, 2024 – Jan 27, 2024
Mile 0 Fest
https://www.mile0fest.com/
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. Single day passes may become available, but are not guaranteed. Performances take place at Coffee Butler Amphitheater, 21 Quay Rd. and at other locations around Key West. Talent includes Morgan Wade, Tanner Usery, the Randy Rogers Band and many more.
Jan 31, 2024 – Feb 3, 2024
Key Western Fest
https://www.keywesternfest.com/
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.
Feb 24, 2024 – Feb 25, 2024
Key West Art & Craft Festival
https://keywestartcenter.com/kw-art-%26-craft-festival-1
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.
Mar 1, 2024
South Florida Symphony: Masterworks III – Beethoven’s Ninth, Grand Opera Finales
https://www.tix.com/ticket-sales/southfloridasymphony/5590/event/1319159
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.
Mar 11, 2024 – Mar 14, 2024
March Merkin Invitational Permit Tournament
https://marchmerkin.com/
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.
Mar 29, 2024
South Florida Symphony: Masterworks IV – Stravinsky, Ravel, Bernstein, Zwilich
https://www.tix.com/ticket-sales/southfloridasymphony/5590/event/1319159
The program features a stirring elegy on 9/11, the high-octane spirit of 1940s Times Square, a sensuous Spanish tavern, and an epic Russian fairytale come vividly to life in these works by masterful composers. Tennessee Williams Theatre, 5901 College Rd. 7:30 p.m.
Apr 4, 2024 – Apr 6, 2024
Legends of Music Row Music Festival
https://www.legendsofmusicrow.com/
Book your tickets for this extraordinary event, including an option for a VIP experience on April 3rd with an exclusive, up-close-and-personal concert setting featuring songwriting legends in country music. A musical experience like no other, Legends of Music Row is to be hosted by Country Music Hall of Fame songwriter Dean Dillon with nightly concerts at Coffee Butler Amphitheater. The 2024 Legends lineup includes Tracy Byrd, Kelli Pickler, Wood Box Heroes, Brice Long and Marla Cannon-Goodman.
Apr 19, 2024 – Apr 24, 2024
42nd Annual Conch Republic Days
https://conchrepublic.com/
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.
May 1, 2024 – May 5, 2024
28th Annual Key West Songwriters Festival
https://keywestsongwritersfestival.com/
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 website, keywestsongwritersfestival.com.
Jun 5, 2024 – Jun 9, 2024
Key West Pride
https://gaykeywestfl.com/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 27, 2024 – Jun 30, 2024
Seventh Annual Mango Fest Key West
https://mangofestkeywest.com/
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.
Jul 16, 2024 – Jul 21, 2024
Hemingway Days
https://fla-keys.com/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.
Oct
FANTASY FEST 2024 – coming soon
https://www.fantasyfest.com/
This outrageous 10-day costuming and masking celebration features flamboyant masquerade competitions, and over 30 cleverly themed Parties and performances. Togas, Tutu’s, Body Paint and Burlesque, Halo’s, and Homemade Bikinis. Join the fun!