Events & Festivals

June – July 2018

  • Jun. 6, 2018 – Jun. 10, 2018
    Key West Pride
    Matt Hon 305-294-4603
    Key West shows its Pride every day, and this is your chance to be a part of the celebration! The five-day schedule includes daytime pool and beach parties, late-night drag shows, on-the-water adventures ranging from snorkeling and kayaking to glass-bottom boat tours, a street fair, a 10k relay for tutu-wearing runners and walkers, and pageants to select Mr., Miss and Ms. Key West Pride.

  • June 9, 2018
    Sixth Annual VFW Fishing Tournament
    Pete Thomas 610 304 2392 
    Sponsored by the Southernmost VFW Post 3911, this family oriented inshore and offshore tournament offers cash prizes for dolphin, wahoo, tuna, snapper and grouper, along with prizes for heaviest fish by a lady angler, heaviest fish by a juvenile angler, pee-wee, senior angler and active service member. The heaviest Dolphin: 1st-$3000.00; 2nd-$1000.00; and 3rd $500.00. Weigh-in at Murray Marine. All proceeds benefit VFW Relief Fund for Monroe County veterans, and local charities.

  • Jun. 16, 2018
    Swim Around Key West
    The Annual Swim Around Key West is a 12.5-mile endurance swim clockwise around the entire island of Key West. This is the 41st swimming of our event, started by founder Anna Fugina in 1977. The Annual Swim Around Key West is an independent and insured swim, permitted by the U.S. Coast Guard. There are three categories: solo swimmer, two-person relay team and three-person relay team. Presented by Key West Athletics Association. Deadline for registration applications is May 18, 2018.

  • Jun. 22, 2018 – Jun. 24, 2018
    Fifth Annual Mystery Fest Key West
    305-587-9392 
    2018 headliners are Keynote Speaker Ace Atkins, the multi-award winning, New York Times bestselling author of twenty-one novels, including the recent Robert B. Parker “Spenser” mysteries; Special Guest of Honor, the multi-award winning editor and publisher Otto Penzler – proprietor of the famed The Mysterious Book Shop in New York City; and Special Guest Presenter, New York Times and USA Today bestselling author Heather Graham. Fest highlights include panels, presentations and parties with some two-dozen high profile and award-winning authors, book signings, professional publishing and marketing discussions, presentation of the 2018 Whodunit Mystery Writing Competition and Award, a mini Conch Train tour, and social events at different landmark locations in the Southernmost City of the United States.

  • Jun. 29, 2018 – Jul. 1, 2018
    Key West Island Swim: FKCC Swim Around Key West
    Lori Bosco 305-809-3562 
    The officially sanctioned event (June 30) is a 12.5-mile swim clockwise around the island of Key West that is open to all age groups. Individual swimmers and relay teams can compete. The route takes swimmers through the waters of the Atlantic Ocean and Gulf of Mexico, ending where they began at Higgs Beach.

  • Jun. 30, 2018 – Jul. 4, 2018 
    Sixth Annual Key Lime Festival

    A wacky talent show, pie-eating and cooking contests and other tasty temptations await Key West visitors during the annual Key Lime Festival. Four days of culinary events for every taste are planned, including favorites from past years like the Key Lime Cocktail Sip & Stroll, and new favorites for Key Lime lovers like The Key Lime Pie Hop.

  • Jul. 4, 2018 
    Rotary Club of Key West Annual Fireworks Show

    305-304-6963 
    Since 1976, the Rotary Club of Key West has presented the island’s annual fireworks show. Staged from the Edward B. Knight Pier (formerly called White Street Pier) overlooking the Atlantic Ocean where White Street meets Atlantic Avenue, fireworks are to begin at 9 p.m. Attendees can purchase food, drinks, burgers and hot dogs to benefit the Rotary Club’s scholarship funds at a booth across from the pier on Atlantic Avenue.

  • Jul. 12, 2018 – Jul. 14, 2018 
    Mel Fisher Days

    305-296-6533 
    Come commemorate the anniversary of Mel Fisher’s famous 16-year search for the Spanish galleon Atocha and the discovery of the Atocha Mother Load . Annual Dock Party at Schooner Wharf Bar, with tours of salvaging vessels, raffle, silent and live auctions and live entertainment. Proceeds from these events are to benefit Wesley House Family Services, Inc.

  • Jul. 15, 2018 – Jul. 18, 2018 
    Del Brown Permit Tournament

    Loren Rea 305-360-6969 
    Anglers fly-fish on the flats in a challenge that honors the late angling pioneer Del Brown, who caught and released 513 permit on fly tackle off the Florida Keys in his lifetime. The tournament is based out of Hurricane Hole Marina.

  • Jul. 17, 2018 – Jul. 22, 2018 
    Hemingway Days

    (305) 296-2388 (Look-Alike); 797-0579 (literary)
    The 38th annual celebration of the legendary author’s work and lifestyle features literary readings, the Running of the Bulls, a short story competition, fishing tournament, 5k Run and Paddleboard Race, Sloppy Joe’s Look-Alike Contest and a birthday “party” commemorating Ernest’s July 21st birthday.

  • Jul. 19, 2018 – Jul. 21, 2018 
    Sloppy Joe’s 38th annual “Papa” Hemingway Look-Alike Contest

    The look-alike challenge takes place at Sloppy Joe’s Bar, 201 Duval St., frequented by Hemingway when he lived and wrote on the subtropical island throughout the 1930s. The contest’s preliminary rounds are set for 6:30 p.m. Thursday and Friday, July 19 and 20, and the newest “Papa” is to be chosen during a final round beginning at 6:30 p.m. Saturday, July 21.

  • Jul. 21, 2018 
    26th Annual Hemingway 5K Sunset Run/Walk & Paddleboard Race

    Barb Wright at 305-240-0727 
    This is the original and oldest ongoing 5K Run in Key West and takes place as part of the the annual Hemingway Days Festival. The race course is a scenic flat course that runs past Key West’s most famous landmarks including the Ernest Hemingway Home, the iconic Southernmost Point and the famous Green Parrot Bar. Visit website for more details.