32nd Anniversary Hemingway Key West 5K Sunset Run &
Paddleboard Race

Saturday, July 24, 2021


We will have the original courses in addition to some optional ones for both the 5k Run and Paddleboard Race (you can do them all if you wish). Participants will have a four-day window to complete the events. The technology we are using for our events will digitize the race courses.

2021 Race Shirt & Medal Coming Soon!

2020 Hemingway 5K Sunset Run & Paddleboard Race Shirt, Medal and and
UPF 50 Kool Wrap!

We will be using RaceJoy to monitor and guide your progress along the course and allow your friends and family members to follow along, as well.

RaceJoy is a free app that you will run on your phone that will use the GPS capabilities to track your progress and send you alerts at critical  parts of the course. Additionally, as you pass each mile, you will get a message indicating your progress and current pace. When you complete the course, you can send your results in to be shared online (you will receive a bib number that will be used for tracking your results). The app is free and very easy to set up and use. You should take a few minutes to learn how to get set up prior to race day:

Spectator / Participant Tutorial:  RaceJoy User Tutorial

RaceJoy User Tutorial

SO there is no reason not to run the Hemingway 5K and/or Paddleboard race and the best part is, you can now run it any time you want between July 23 and July 26  HERE OR in your hometown!

You will have a choice of three 5K run courses and two Paddleboard courses. The 5K course will be the original Hemingway 5K Run by the Southernmost Point, the Key West Half Marathon 5K course at the Historic Seaport and a no traffic option along the water on South Roosevelt Blvd.

We are working on several other activities for you to do on your own with friends or family – Paddle activities with Lazy Dog Outfitters, a Hemingway Trivia Hunt and Rum tastings with a raffle. Stay tuned for updates.

Original 5K course:

KWHM 5K Course:

Smather’s Beach Course:

Original Paddle course:

Lazy Dog Paddle Course:

Tour of Key West Course:

New! Free* Hemingway Trivia Hunt!

Trivia buffs: How much do you know about Ernest Hemingway? Wander around town, testing your knowledge with our new Trivia Hunt, which takes you to some of Ernest’s haunts, notable places where he spent time, and sites that honor him.

Email your request tokeywesthalfmarathon@gmail.com for the printable game by 10:00 any morning — Thursday-Monday, (7/23-7/27). The game will be emailed to you, and answers must be returned by 5:00 that night.

Win entries to next year’s Hemingway 5K & Paddleboard Race, entries to the Key West Half Marathon, and more!

(*Please note: admission to 2 places is required — $24/adult, total.)

Enter the Raffle to Win a Bottle of Rum! 

(Stop by 105 Simonton St. and drop your bib’s raffle ticket into the jar, or write your bib number on a piece of paper and drop in. Drawings (2 bottles, total) on Sunday, July 26th.)

Key West First Legal Rum Distillery is Key West’s first legal rum distillery since Prohibition. Chef Paul Menta’s award-winning Key West rums are aged in Salt Cured Barrels using locally and naturally-sourced authentic food flavors–Key Lime, Coconut, Madagascar Vanilla crème brûlée–and Florida demerara sugar (never molasses) to produce a rum with flavor depths and aromatic heights worthy of the distinction: Chef Distilled®.

Join their Mojito-making class! Call or stop by for details.

(305) 294-1441/keywestlegalrum.com


Mail to:

Hemingway Sunset Run
P.O. BOX 1681,
Key West, FL 33041

Make Checks Payable to: Hemingway Sunset Run LLC.

Runners, walkers and paddleboard enthusiasts can test their skills and celebrate Ernest Hemingway’s sporting lifestyle Saturday, July 25, 2020 during the Hemingway 5k Sunset Run and Paddleboard Race. The 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.


 Paddleboard Rentals for the Hemingway Paddleboard Race

*You must have a Personal Flotation Device with you during the race

Call Lazy Dog Outfitters at
305-295-9898 to rent Paddleboards

$25.00 Delivery to Race Start
and Return by Lazy Dog!


Mellow Ventures

Paddleboard rental info:
*1 hour dockside $25
*2 hour dockside $35
*4 hour take away $45
*Full day $65
*Weekly rates available


Call Standup Paddleboard
Key West
at 305-240-1426
to rent 

SUP Key West
501 5th Ave


Paddleboard Rental Companies

*You must have a Personal Flotation Device with you during the race.

  • Lazy Dog 305-295-9898
  • Java Cat  305-294-7245
  • Mellow Ventures   305-745-3874 
  • Sunset Watersports   305-296-2554
  • Fury  855-421-4085
  • Ibis Bay  305-896-0342
  • SUP KeyWest   305-240-1426
Contact Us

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