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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

  • May 31 Key West
  • Key West Art & Historical Society: Beaches, Creatures & Cowboys - Florida Movie Posters Exhibit Opening
  • Website
  • The public is invited to celebrate the opening of the society's newest exhibit at the Customs House Museum, 281 Front St., Friday from 5 to 7 p.m. "Beaches, Creatures & Cowboys: Florida Movie Posters" celebrates filmmaking in Florida. The 40 classic posters that form part of the display include artwork for “Beneath the 12 Mile Reef,” “Cocoon,” “Flipper,” and “Operation Petticoat." The exhibit runs through September 1, 2024.

  • June 01 Key West
  • Key West Theater: Pride Follies
  • Website
  • The Key West Business Guild opens this year’s PRIDE month with Pride Follies, showing at the Key West Theater, 512 Eaton St. Pride Follies began 17 years ago to give Key West performers who usually perform in bars and restaurants the chance to appear on the professional stage. 2017 Fantasy Fest Queen Destiny Montgomery again directs this year’s production filled with comedy, singing, and dancing. Doors open at 6 p.m.; show at 7 p.m.

  • June 01 Key West
  • Royal Poinciana Red Party
  • Website
  • Red attire is encouraged at this annual event at the Key West Lighthouse & Keepers Quarters, including live music, lite bites, a silent auction and sales of books, calendars and trees. Proceeds benefit the replanting of quality trees in Key West. 6 to 9 p.m. 938 Whitehead St.

  • June 05 Key West
  • Key West Pride: Kick-Off Disco Party
  • Website
  • Don't miss the Disco Party to kick off Key West's 2024 Pride celebration from 5:30 to 7:30 p.m. at Hard Rock Cafe, 313 Duval St. $25 at the door includes food, drinks and a disco dance party.

  • June 05 - 09, 2024 Key West
  • Key West Pride
  • Website
  • 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!

  • June 07 Key West
  • Coffee Butler Amphitheater: Billy Currington
  • Website
  • Well-known for his smooth and distinct voice and songs including "Don't Hurt Like it Used To" and "People Are Crazy," Billy Currington comes to the amphitheater with opener Mike Stack. Doors open at 6 p.m.; show at 7:30 p.m. 21 E. Quay Rd.

  • June 08 Key West
  • Big Gay 5k
  • Website
  • The second annual Big Gay 5k race takes place on Saturday, June 8 during Key West Pride. The start and finish line is the famous Rainbow Crosswalk on Duval Street. The race starts at 8 a.m. and is to be followed by "The World's Most Fabulous Post-Race Party" at 22 & Company, 504 Angela St., which will include awards for Most Spirited, Best Hair, Hottest Socks and more. Register in advance at RunSignUp.com.


  • June 08 Key West
  • College of the Florida Keys Swim Around Key West
  • Email Website
  • 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 09 Key West
  • Sheriff’s Animal Farm Open House
  • Website
  • Visit the family-friendly Monroe County Sheriff's Animal Farm, open the second and fourth Sundays of each month from 1 to 3 p.m. Visits are free of charge, but donations are always welcomed. Stock Island Detention Center, 5501 College Rd.

  • June 09 Key West
  • Key West Pride Parade
  • Website
  • The Key West Pride Parade theme this year is "Celebrating the 70s Disco Era." The parade begins at 5 p.m. at the Quay at Truman Waterfront Park, traveling to Duval Street and ending at United Street.

  • June 11 - 15, 2024 Key West
  • Fringe Theater at the Armory: Miss Abigail's Guide to Dating, Mating & Marriage
  • Website
  • This big hearted and interactive evening of hands-on and somewhat questionable relationship guidance will help set you on the path to dating, mating, and marriage. Love Guru Miss Abigail and her devoted assistant Paco help you “gussy up your love life” with a show that is one part advice, one part fun and games, and one part true love in the making. Doors open at 6:30 p.m.; show begins at 7 p.m. The show takes place at the Armory, 600 White St.

  • June 15 Key West
  • Harry S. Truman Little White House: Truman's Tropical Fruit Festival
  • Website
  • 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 21 - 23, 2024 Key West
  • Key West Gator Club Dolphin Derby
  • Website
  • Anglers targeting dolphin fish can compete for $15 thousand in guaranteed cash prizes during the Key West Gator Club Dolphin Derby June 21 through 23, with weigh-ins and tournament activities at Beachside Resort & Residences, 3841 N. Roosevelt Blvd. The team weighing in the heaviest dolphin fish takes home a grand prize of $5 thousand. Proceeds benefit scholarships for Key West High School graduates attending University of Florida.

  • June 23 Key West
  • Sheriff’s Animal Farm Open House
  • Website
  • Visit the family-friendly Monroe County Sheriff's Animal Farm, open the second and fourth Sundays of each month from 1 to 3 p.m. Visits are free of charge, but donations are always welcomed. Stock Island Detention Center, 5501 College Rd.

  • July 03 - 07, 2024 Key West
  • Key West Key Lime Festival
  • Website
  • 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 gravity-defying 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.

  • July 04 Key West
  • Rotary Key West 4th of July 5k Walk/Run
  • Website
  • Get a healthy start to the 4th of July with Key West Rotary's annual 5k walk/run. Register online in advance at the starting line the morning of the race at Edward B Knight/White Street Pier, 1801 White St. Race starts at 7:30 a.m.

  • July 13 Key West
  • Studios of Key West: One Night Stand
  • Website
  • Since 2007, "One Night Stand, the 24 Hour Theater Project" has prompted creative thinkers to develop new theater from start to finish in only 24 hours. With the clock ticking, dozens of people work together at a wickedly fast pace to write, memorize, rehearse, create backdrops and sets, and comb the island for costumes and props. The result? Four brand new pieces of theater presented in front of a live audience. Performances at 7 and 9 p.m. in the Helmerich Theater. 533 Eaton St.

  • July 14 - 16, 2024 Key West
  • 12th Annual VFW Fishing Tournament
  • 610-304-2392 Email Website
  • Cash prizes are to be awarded for the heaviest catch of five target species -- mahi-mahi (dolphin fish), wahoo, tuna, snapper and grouper, with a first-place prize of 5 thousand dollars for the heaviest mahi-mahi. Anglers fish in seven divisions: pee-wee, junior, lady, first responder, veteran, senior and active duty. Captains and anglers can choose to fish either Saturday or Sunday, or both if they register separately for each day. All proceeds benefit disabled and needy veterans of Monroe County.

  • July 17 - 21, 2024 Key West
  • Hemingway Days
  • Website
  • Ernest Hemingway look-alikes, writers, anglers, and fans of the late author’s work are to gather in Key West Wednesday through Sunday, July 17-21 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.

  • July 17 - 20, 2024 Key West
  • Key West Marlin Tournament
  • Website
  • Coinciding with the 44th annual Hemingway Days celebration, anglers ply the waters once fished by novelist Ernest Hemingway, vying for $50,000 in guaranteed cash prizes in the marlin division. The event awards $25,000 to the first-place team with the most points for blue marlin, white marlin and spearfish. Teams can enter one fun fish (dolphin, tuna, wahoo or released sailfish) per day for additional points. Entry is limited to the first 75 boats. Tournament events are based out of the Perry Hotel & Marina, 7005 Shrimp Road.

  • July 20 Key West
  • Hemingway 5k Sunset Run & Paddleboard Race
  • Website
  • 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.