Key West Half Marathon & 5K
Make Ocean Key your home base for the Key West Half Marathon and 5K. With plenty of opportunity to rest up before the big race and indulgence after, make the most of your marathon weekend at the Southernmost City’s most iconic address
Race Details
Recognized by Runner’s World as one of the 10 best winter half marathons, this competitive race follows a 13.1-mile course through Old Town Key West, past historic landmarks and the island’s scenic waterfront. Runners cross the Cow Key Channel, pass through CB Harvey Rest Beach Park and down Duval Street, Eaton Street and Whitehead Street.
Events Calendar
Good times and good vibes are always on deck. Check out our activities and the local music scene at Ocean Key Resort and Sunset Pier.
Aug22Sunset 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 - December 31, 2026
Time: Saturday's, Varies (sunset)
Location: Off-Site (Key West waters)
Aug23World 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 - December 31, 2026
Time: Sunday's, Varies by charter
Location: Off-Site (Florida Keys waters)
Aug25Double Dip Snorkel Trip
Explore the turquoise waters of the 3rd largest coral barrier reef, teeming with fish, coral, sea turtles and more.
Date: May 12, 2026 - December 31, 2026
Time: Tuesday's, 2:00 pm – 5:00 pm
Location: Off-Site (Catamaran / Key West reef)
Aug27Haunted Tours
Explore the SPOOKY side of Key West with a haunted historical tour.
Date: May 14, 2026 - December 31, 2026
Time: Thursday evenings (varies by operator)
Location: Off-Site (Key West – walking or trolley tour)
Aug27Ocean Key Lime Bike Tour
Sightseeing the Key West way with a leisurely island bike tour that can be done in flip flops!
Date: May 14, 2026 - December 31, 2026
Time: Thursday's, 10:00 am – 12:00 pm
Location: Key West (guided bike tour)
Aug27Key West Farmers Market
Visit the Key West Farmers Market every Thursday at the Truman Waterfront.
Date: May 14, 2026 - December 31, 2026
Time: Thursday's, 2:00 pm – 7:00 pm
Location: Truman Waterfront
Aug28Snorkel 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 - December 31, 2026
Time: Friday's, varies by tour operator
Location: Off-Site (Catamaran / Key West waters)
Oct16Fantasy Fest
Fantasy Fest turns Key West into a spectacle of masked processions, parties, contests and dances attended by tens of thousands.
Date: October 16 -25, 2026
Time: Varies by event
Location: Key West (multiple venues)
Oct17That Arena Rock Show
Kick of Fantasy Fest 2026 with iconic rock music over the water on the world-famous Sunset Pier.
Date: October 17 & 18, 2026
Time: 7:00 PM
Location: Sunset Pier
- Oct20
Tay Tay Tuesday, Life of a Showgirl
Join us for a family-friendly tribute to your favorite musical icon and showgirl.
Date: October 20, 2026
Time: 6:00 PM
Location: SpaTerre
