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A group of people dressed as Hemingway at Hemingway Days

Hemingway Days

Fans of Ernest Hemingway’s literary greatness and vigorous life – including scores of bearded Hemingway look-alikes – converge on Key West for Hemingway Days 2026. The annual celebration salutes the Nobel Prize-winning author’s writing achievements, sporting pursuits and enjoyment of the island’s easygoing lifestyle. The festival’s undisputed highlight is the Hemingway Look-Alike Contest at Sloppy Joe’s Bar, a frequent hangout during the writer’s 1930s residence in Key West – preliminary and final rounds run July 26.

Date

July 23 - 27, 2026

Time

Varies by event

Location

Key West (Sloppy Joe's Bar, 201 Duval St., and other venues)

Learn More

Calendar of Events

  • Purple and pink orchids with some wellness lotions
    Jun05

    SpaTerre Body Scrub Special

    Coconut Crush Body Renewal. Exfoliating brown sugar and Tahitian Coconut Shells buff away tired skin cells to allow maximum hydration.

    Date: May 15 - June 28, 2026

    Time: Friday's, All day (by appointment)

    Location: SpaTerre

  • A woman snorkelling with a sail boat in the water
    Jun05

    Snorkel Experience

    Dive into the 3rd largest coral barrier reef in the world and the only barrier reef in the continental United States.

    Date: May 8 - June 26, 2026

    Time: Friday's, varies by tour operator

    Location: Off-Site (Catamaran / Key West waters)

  • 2 large sailboats on the water during a gorgeous sunset
    Jun06

    Sunset Sails

    There is nothing quite like a Key West sunset, and the second-best place to view one (after the Sunset Pier, of course) is out on the water.

    Date: May 9, 2026 - June 27, 2026

    Time: Saturday's, Varies (sunset)

    Location: Off-Site (Key West waters)

  • A man offshore fishing
    Jun07

    World Class Fishing

    The Florida Keys are known for amazing fishing. From the flats and shallows, sight fishing for permit, tarpon or bonefish or in the deeper waters of the backcountry, on the hunt for snapper, grouper or tuna.

    Date: May 10, 2026 - June 28, 2026

    Time: Sunday's, Varies by charter

    Location: Off-Site (Florida Keys waters)

  • Alvarez Brunch Food
    Jun07

    Sunday Brunch

    Come experience one of the Island’s best waterfront brunches featuring unlimited traditional Florida and Caribbean inspired shareable plates.

    Date: May 17, 2026 - June 28, 2026

    Time: 11:45 am – 12:45 pm

    Location: Hot Tin Roof

  • 2 people on a Fury Snorkel
    Jun09

    Double Dip Snorkel Trip

    Explore the turquoise waters of the 3rd largest coral barrier reef, teeming with fish, coral, sea turtles and more.

    Date: May 12, 2026 - June 30, 2026

    Time: Tuesday's, 2:00 pm – 5:00 pm

    Location: Off-Site (Catamaran / Key West reef)

  • Scavenger Hunt sign with wooden destination arrows
    Jun10

    Zero Duval Scavenger Hunt

    Experience a one-of-a-kind, interactive scavenger hunt in the downtown area of Old Town, starting at Zero Duval.

    Date: May 13, 2026 - June 24, 2026

    Time: Wednesday's, 10:00 am – 12:00 pm

    Location: Old Town Key West (starts at Zero Duval)

  • A woman with a mud mask on her back at the spa
    Jun11

    SpaTerre VOYA Treatments

    Relax and rejuvenate the natural way! VOYA Organic Seaweed Treatments.

    Date: May 14, 2026 - June 25, 2026

    Time: Thursday's, All day (by appointment)

    Location: SpaTerre

  • Process Of Doing Hardware Procedure With Ultrasound Apparatus
    Jun11

    SpaTerre VOYA Treatments

    Vortex Cleansing deeply cleanses and hydrates, Hydrapeel exfoliation resurfaces without irritation

    Date: May 12, 2026 - June 30, 2026

    Time: Tuesday's, All day (by appointment)

    Location: SpaTerre

  • A lantern in the ground in a dark room and a ominous shadow in the background
    Jun11

    Haunted Tours

    Explore the SPOOKY side of Key West with a haunted historical tour.

    Date: May 14, 2026 - June 25, 2026

    Time: Thursday evenings (varies by operator)

    Location: Off-Site (Key West – walking or trolley tour)