

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 MoreCalendar of Events
Jul21Double 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 - July 31, 2026
Time: Tuesday's, 2:00 pm – 5:00 pm
Location: Off-Site (Catamaran / Key West reef)
Jul21Live 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
Jul22Zero 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 - July 31, 2026
Time: Wednesday's, 10:00 am – 12:00 pm
Location: Old Town Key West (starts at Zero Duval)
Jul22Muddle & 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
Jul22Live 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
Jul23SpaTerre 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
Jul23SpaTerre 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
Jul23Haunted 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)
Jul23Romance 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
Jul23Ocean 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)