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.
Filter By:
Aug13
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)
Aug13
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
Aug14
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)
Aug15
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)
Aug16
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)
Sep03
Music
Just a Few Friends, Favorite Son Celebration
Just a Few Friends is a one-of-a-kind festival celebrating music, community, and island life in beautiful K...
Date: September 3 - 11, 2026Time: Varies by eventLocation: Key West (multiple venues)