There is always something fun to do in Key West. This calendar of events is frequently updated.
Key West’s Most Complete Calendar of Events.
This calendar of events for Key West includes nearly every happening on the island throughout the year. Something missing? If you know of any Key West calendar events that we have overlooked please let us know by filling out this short form and we’ll quickly add it. Check back frequently: more events, dates, and details are added as the season progresses.
If you have an event you would like to add to our calendar, visit this page to submit your event details: https://www.keywesttravelguide.com/submit-your-event-for-the-key-west-calendar/
2024 Key West Upcoming Events Calendar
May 26, 2024 – LOCAL COLOR – 33RD ANNUAL MINIMAL REGATTA AT SCHOONER WHARF BAR – With little more than a sheet of plywood and ducktape, contestants build a simple boat and compete in a variety of humorous categories. More information here.
May 27, 2024 – MARITIME – 15 YEAR VANDIVERSARY – Celebration of the 15th anniversary of the sinking of the USS Vandenberg, now an artificial reef and popular wreck-diving spot.
Jun 5 – 9, 2024 – LGBTQ – Key West Pride Fest – Event honoring diversity, openness and freedom in the city that is consistently recognized as one of the world’s top gay and lesbian vacation destinations. Includes a mix of: Dance and cocktail parties, contests, shows, forums, activities on the water, tours, street fair and the Pride Parade along Duval Street. Street fair in June 8, 10am-7pm on Duval Street. Pride parade is June 8th at 4pm on Duval Street. More information here.
June 7 – 9, 2024 – FISHING – 31ST ANNUAL DOLPHIN TOURNAMENT – Offshore fishing tournament for summer favorite dorrado, aka mahi-mahi, and locally known as dolphinfish. More information here.
July 17 – 21, 2024 – HEMINGWAY – SLOPPY JOE’S 43RD ANNUAL HEMINGWAY LOOK-ALIKE CONTEST – Over 100 Hemingway look-a-likes compete for prizes and notoriety as most resembling the famous writer, judged by previous contest winners. Sloppy Joe’s Bar – 6:30 pm – 201 Duval Street.
July 20 – 21, 2024 – RUNNING – 35TH ANNIVERSARY HEMINGWAY 5K SUNSET RUN & PADDLEBOARD RACE – Running race through Key West. The event has expanded to include a paddleboard competition. Cost is $45-85 to register, depending on which events you participate in. More information here.
August 7 – 11, 2024 – LGBTQ – Tropical Heat – All male, adults-only celebration of Key West’s gay community and lifestyle. Events include all-male themed parties and adult-oriented entertainment. For more information, call the Key West Business Guild at 305-294-4603.
August 8 – 11, 2024 – SEAFOOD – 27th Annual Key West Lobsterfest – Everyone will be partying on Duval Street, except the lobsters. Marking the official opening of lobster season, this crustacean-focused event features street fairs, live music, and arts & crafts. Street fair with free live concert on Saturday, noon-11pm, lower Duval Street. More information here.
September 4 – 8, 2024 – LGBTQ – Womenfest Key West – Lesbians and friends converge on Key West for a week of activities, including late night dancing, pool parties, comedy shows, sunset sails, competitive bull riding, and lots of music. More information here.
October 13, 2024 – RUNNING – SoMo Marathon & Half Marathon – Running race through Key West and up the “lower Keys” with views of the Gulf of Mexico and the Atlantic Ocean. Distances of full marathon (26.2 miles) and half-marathon (13.1 miles). More information here.
October 18 – 27 – LOCAL COLOR – Key West Fantast Fest – Week-long celebration and Key West’s biggest party of the year – with many adult-only events. This year’s theme is “It’s a 90s Neon Cosmic Carnivale”. More information here.
October 20, 2024 – LOCAL COLOR – Zombie Bike Ride – Costumed bike ride when 1000 zombies ride throughout Key West to the Truman Waterfront Park. More information here.
October 24, 2024 – LOCAL COLOR – Key West Headdress Ball – Costume contest featuring dazzling headdresses created over many months and worn and displayed in this awe inspiring event. HUGE works of art, each more inventive and imaginative then the previous. More information here.
November 3 – 10, 2024 – MARITIME – Race World Offshore World Championship – Considered the pinnacle of offshore powerboat racing. Top powerboat & superboat offshore racers compete for title of World Champion. Spectators line the Key West harbor to see the 100+ mph action. More information here.
November 20 – 24, 2024 – FILM – Key West Film Festival – Features independent cinema with awards for narrative feature film, LGBT feature film, documentary, Florida feature film, and foreign feature film. Events include movie screenings, kick-off party, and awards gala. More information here.
December 14, 2024 – HOLIDAY – Schooner Wharf Lighted Boat Parade – Vessels of every size and shape deck their hulls and light up the night with their creativity and originality to the delight of locals and visitors alike. Santa Claus has been spotted at the helm, ditching his sleigh for a center console or sailboat with mistletoe hanging from the mast. His first mates have included gingerbread men and the Grinch. Other times, dolphins have replaced cold-weather reindeer, ushering in Santa’s sleigh packed with lighted presents. More information here.
December 31, 2024 – HOLIDAY – Key West New Year’s Eve – Celebrations include the lowering of the Conch Shell over Sloppy Joe’s on lower Duval Street, the lowering of famous Key West drag queen Sushi (riding a huge high-heeled shoe) over the Bourbon Street Complex on upper Duval Street, and the lowering of the “pirate wench” from the mast of a schooner in the Historic Seaport.
If you know of any Key West calendar events that we have overlooked please let us know by filling out this short form and we’ll quickly add it. And check back frequently – since more dates and details will be added as the season progresses.