Run Key West

Register for the Key West Bundle and SAVE 20% on the
34th Annual Hemingway 5K Sunset Run & Paddleboard Race on July 22, 2023
and 26th Annual Key West Half Marathon on January 14th, 2024.

Look for Key West Bundle on Runsignup.com registration page!


Race through Key West’s historic Old Town and waterfront areas January 14, 2024, during the annual Key West Half Marathon®. The field is quickly filling to capacity. Set to begin at 7 a.m., the sporting challenge takes place on a flat, fast 13.1-mile half-marathon course in the scenic island city. Location of this year’s run is the Key West Historic Seaport at the foot of Margaret Street. The 5K Run will follow right after the start of the Half Marathon.

Now celebrating our 26th Anniversary, we have had participants from all 50 States and 27 countries, including Great Britain, Canada, Mexico, Switzerland, Spain, Italy, India, China, South Pacific, Iceland, Sweden, Norway, Brazil to name a few to compete in Key West’s balmy January climate.


Old Town Key West will host runners, fitness walkers and paddleboard enthusiasts testing their skills and celebrating Ernest Hemingway’s sporting lifestyle on Saturday evening, July 23rd. The longest on-going race in Key West, the Hemingway 5K Sunset Run/Walk and Paddleboard Race, presented by Papa’s Pilar Rum, was rated in 2018 #3 on Active.com’s list of top ten international destination races to turn into a vacation.

The well-established athletic challenges are part of Hemingway Days, a six-day commemoration of the life and work of the author who lived and wrote in Key West for most of the 1930s.

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