Key West Events Calendar
There’s always something happening in Key West. Discover local activities and seasonal events, or enjoy live music at the famous Sunset Pier, located at our sister property, Ocean Key Resort & Spa.
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Jul23
Island Experiences
Hemingway Days
Fans of Ernest Hemingway’s literary greatness and vigorous life – including scores of bearded Hemingw...
Date: July 23 - 27, 2026Time: Varies by eventLocation: Key West (Sloppy Joe's Bar, 201 Duval St., and other venues)
Jul23
Island Experiences
Haunted Tours
Explore the SPOOKY side of Key West with a haunted historical tour.
Date: May 14, 2026 - July 31, 2026Time: Thursday evenings (varies by operator)Location: Off-Site (Key West – walking or trolley tour)
Jul23
Art
Key West Farmers Market
Visit the Key West Farmers Market every Thursday at the Truman Waterfront.
Date: May 14, 2026 - July 31, 2026Time: Thursday's, 2:00 pm – 7:00 pmLocation: Truman Waterfront
Jul24
Spa
Be Transformed at SpaTerre
Find tropical serenity at SpaTerre, located within our sister property, Ocean Key Resort & Spa.
Date: Friday's through July 31, 2026Time: All day (by appointment)Location: SpaTerre
Jul24
Island Experiences
Snorkel Experience
Dive into the 3rd largest coral barrier reef in the world and the only barrier reef in the continental Unit...
Date: May 8 - July 31, 2026Time: Friday's, varies by tour operatorLocation: Off-Site (Catamaran / Key West waters)
Jul25
Island Experiences
Sunset Sails
There is nothing quite like a Key West sunset, and the second-best place to view one (after the Sunset Pier...
Date: May 9, 2026 - July 31, 2026Time: Saturday's, Varies (sunset)Location: Off-Site (Key West waters)