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:

2024 Key West Upcoming Events Calendar

May 26, 2024 – LOCAL COLOR33RD 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 – MARITIME15 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 – LGBTQKey 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 – FISHING31ST 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 – HEMINGWAYSLOPPY 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 – RUNNING35TH 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 – LGBTQTropical 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 – SEAFOOD27th 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 – LGBTQWomenfest 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 – RUNNINGSoMo 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 COLORKey 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 COLORZombie Bike Ride – Costumed bike ride when 1000 zombies ride throughout Key West to the Truman Waterfront Park.  More information here.

October 24, 2024 – LOCAL COLORKey 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 – MARITIMERace 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 – FILMKey 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 – HOLIDAYSchooner 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 – HOLIDAYKey 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.

Things to do…everyday!

Ultimate Watersports Package

  3.5-hour trip includes light snacks, beverages, sailing, parasailing, jetskis, and big water toys Want

Waverunner Jet Ski Tours

  Have an absolute BLAST zooming across the water…all the way around the island of

Express Watersports Package

  Three-hour trip includes parasailing, jetskis, kayaks, big water toys, snorkel gear, and tasty snacks

Private Sunset Charters

  Wouldn’t it be nice to have your own boat in Key West? Well you

Sunset Cruise – Glass Bottom Boat

  A great view – above and below deck. Air-conditioned comfort on this Key West

Sunset Sail – Wind & Wine

  An upscale sunset cruise aboard a traditional working schooner – serving premium wine, beer,

Sunset Sails – Schooners & Tall Ships

  Hoist the sails – if you’d like to lend a hand – aboard the

Sunset Sail – Booze Cruise

  Boat trip to see the Key West sunset  – with beverages and an island

Sunset Booze Cruise Concert

  Trop-rock into the sunset on a sailboat! Includes free-flowing beer, wine, margaritas, and snacks


  Like snorkeling, but you can breath underwater thanks to scuba air tanks floating on

Traditional Sailboat Snorkel

  Smaller group, impressive mono-hull sailboat, offering relaxed snorkel trips to the reef This elegant

Private Snorkeling Charters

  Have the boat and Captain to yourself, allowing for custom trips to suit your