Calendar of Events
Jul16Haunted 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)
Jul16Key West Farmers Market
Visit the Key West Farmers Market every Thursday at the Truman Waterfront.
Date: May 14, 2026 - July 31, 2026
Time: Thursday's, 2:00 pm – 7:00 pm
Location: Truman Waterfront
Jul17Be Transformed at SpaTerre
Find tropical serenity at SpaTerre, located within our sister property, Ocean Key Resort & Spa.
Date: Friday's through July 31, 2026
Time: All day (by appointment)
Location: SpaTerre
Jul17Snorkel Experience
Dive into the 3rd largest coral barrier reef in the world and the only barrier reef in the continental United States.
Date: May 8 - July 31, 2026
Time: Friday's, varies by tour operator
Location: Off-Site (Catamaran / Key West waters)
Jul18Sunset Sails
There is nothing quite like a Key West sunset, and the second-best place to view one (after the Sunset Pier, of course) is out on the water.
Date: May 9, 2026 - July 31, 2026
Time: Saturday's, Varies (sunset)
Location: Off-Site (Key West waters)
Jul19World Class Fishing
The Florida Keys are known for amazing fishing. From the flats and shallows, sight fishing for permit, tarpon or bonefish or in the deeper waters of the backcountry, on the hunt for snapper, grouper or tuna.
Date: May 10, 2026 - July 31, 2026
Time: Sunday's, Varies by charter
Location: Off-Site (Florida Keys waters)
Jul23Hemingway Days
Fans of Ernest Hemingway’s literary greatness and vigorous life – including scores of bearded Hemingway look-alikes
Date: July 23 - 27, 2026
Time: Varies by event
Location: Key West (Sloppy Joe's Bar, 201 Duval St., and other venues)
Sep03Just 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 Key West over Labor Day Weekend.
Date: September 3 - 11, 2026
Time: Varies by event
Location: Key West (multiple venues)
Nov01Race World Offshore Championships
Experience the most powerful of water activities in Key West with the Race World Offshore World Championships.
Date: November 1 - 8, 2026
Time: Daytime (race schedule varies)
Location: Key West (Gulf side – six-mile course)
