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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

  • Refreshing mojito cocktail with mint and dried lime on green tile at Ocean Key Resort, Key West, Florida
    Jul15

    Muddle & Mingle

    We invite locals and resort guests to a spirited midday escape, blending cocktail craft, island flavor and Sweet Bird flair.

    Date: July 6, 2026 - August 30, 2026

    Time: 12:00 PM

    Location: Sweet Bird Bar

  • Live rockabilly music at Sunset Pier, Ocean Key Resort, Key West, Florida — Jerico band on stage
    Jul15

    Live at Sunset Pier – Jerico Rockability Quartet

    Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.

    Date: Wednesdays & Fridays | July 1 - 31, 2026

    Time: 7:00 pm - 9:00 pm

    Location: Sunset Pier

  • A woman with a mud mask on her back at the spa
    Jul16

    SpaTerre VOYA Treatments

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

    Date: May 14, 2026 - July 31, 2026

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

    Location: SpaTerre

  • Process Of Doing Hardware Procedure With Ultrasound Apparatus
    Jul16

    SpaTerre VOYA Treatments

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

    Date: May 12, 2026 - July 31, 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
    Jul16

    Haunted Tours

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

    Date: May 14, 2026 - July 31, 2026

    Time: Thursday evenings (varies by operator)

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

  • Closeup Of Champagne Glasses On Table With Red Roses And Candle
    Jul16

    Romance at Hot Tin Roof

    Add some romance to your dining experience with a chilled bottle of Lallier Reserve Brut champagne and your table decorated with rose petals

    Date: May 14, 2026 - July 31, 2026

    Time: Thursday's, During Hot Tin Roof dining hours

    Location: Hot Tin Roof

  • 3 people biking on a Key Lime Bike tour
    Jul16

    Ocean Key Lime Bike Tour

    Sightseeing the Key West way with a leisurely island bike tour that can be done in flip flops!

    Date: May 14, 2026 - July 31, 2026

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

    Location: Key West (guided bike tour)

  • A mix of fruit at the Farmer's Market
    Jul16

    Key West Farmers Market

    Visit the Key West Farmers Market every Thursday at the Truman Waterfront.

    Date: May 14, 2026 - July 31, 2026

    Time: Thursday's, 2:00 pm – 7:00 pm

    Location: Truman Waterfront

  • Reggae Lou and the Kind Budz performing for a crowd at Sunset Pier, Ocean Key Resort, Key West
    Jul16

    Live at Sunset Pier - Reggae Lou & The Kind Buds

    Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.

    Date: July 16, 21, 23, 28, 30, 2026

    Time: 7:00 pm - 9:00 pm

    Location: Sunset Pier

  • Purple and pink orchids with some wellness lotions
    Jul17

    Be Transformed at SpaTerre

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

    Date: May 15 - July 31, 2026

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

    Location: SpaTerre