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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Oct15
Island Experiences
Haunted Tours
Explore the SPOOKY side of Key West with a haunted historical tour.
Date: May 14, 2026 - December 31, 2026Time: Thursday evenings (varies by operator)Location: Off-Site (Key West – walking or trolley tour)
Oct15
Art
Key West Farmers Market
Visit the Key West Farmers Market every Thursday at the Truman Waterfront.
Date: May 14, 2026 - December 31, 2026Time: Thursday's, 2:00 pm – 7:00 pmLocation: Truman Waterfront
Oct16
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 - December 31, 2026Time: Friday's, varies by tour operatorLocation: Off-Site (Catamaran / Key West waters)
Oct16
Island Experiences
Fantasy Fest
Fantasy Fest turns Key West into a spectacle of masked processions, parties, contests and dances attended b...
Date: October 16 -25, 2026Time: Varies by eventLocation: Key West (multiple venues)
Oct17
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 - December 31, 2026Time: Saturday's, Varies (sunset)Location: Off-Site (Key West waters)
Oct18
Island Experiences
World Class Fishing
The Florida Keys are known for amazing fishing. From the flats and shallows, sight fishing for permit, tarp...
Date: May 10, 2026 - December 31, 2026Time: Sunday's, Varies by charterLocation: Off-Site (Florida Keys waters)