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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Nov02
Island Experiences
Race World Offshore Championships
Experience the most powerful of water activities in Key West with the Race World Offshore World Championshi...
Date: November 1 - 8, 2026Time: Daytime (race schedule varies)Location: Key West (Gulf side – six-mile course)
Nov05
Island Experiences
Haunted Tours
Explore the SPOOKY side of Key West with a haunted historical tour.
Date: May 14, 2026 - March 31, 2027Time: Thursday evenings (varies by operator)Location: Off-Site (Key West – walking or trolley tour)
Nov05
Art
Key West Farmers Market
Visit the Key West Farmers Market every Thursday at the Truman Waterfront.
Date: May 14, 2026 - March 31, 2027Time: Thursday's, 2:00 pm – 7:00 pmLocation: Truman Waterfront
Nov06
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 - March 31, 2027Time: Friday's, varies by tour operatorLocation: Off-Site (Catamaran / Key West waters)
Nov07
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 - March 31, 2027Time: Saturday's, Varies (sunset)Location: Off-Site (Key West waters)
Nov08
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 - March 31, 2027Time: Sunday's, Varies by charterLocation: Off-Site (Florida Keys waters)