Run or Paddle Anywhere

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


For those of you that cannot make it to the race by 7:30pm on July 24, 2021. You can run on your own in Key West anytime or run anywhere using the Race App. And your gear will be shipped to you.


This will be a live event with strict safety protocols but for those who wish to run on their own we will have the original courses in addition to some optional ones for both the 5K Run and Paddleboard Race on RaceJoy. (you can do them all if you wish). Participants will have a four-day window to complete the events of they wish to run with the RaceJoy app on their own.  The technology we are using for the run on your own events will digitize the race courses.

2021 Race Shirt & Medal Unveiled!

Participants running on their own will be using the Racejoy app 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 party is, you have a option for a live event Saturday evening or on your own!

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 for the printable game by 10:00 any morning — Thursday-Monday, (7/22-7/26). 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 25th.)

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/


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 24, 2021 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 Paddleboards

SUP Key West
501 5th Ave

Purchase Your Own Retrospec Inflatable Paddle Board
Participants Receive 20% Off + Free Delivery Anywhere in Key West

Call or visit Sea, Key West downtown Key West to purchase 

(must show proof of race registration to receive discount)

Sea, Key West
702 B Caroline Street

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
  • Sea, Key West  305-741-7490
  • Sunset Watersports   305-296-2554
  • Fury  855-421-4085
  • Ibis Bay  305-896-0342
  • SUP KeyWest   305-240-1426

The Annual Hemingway Bicycle Tour

July 24TH, 2021

Produced by: Key Largo Bike and Adventure Tours

Several years ago a couple of runners started the tradition of riding their bikes to Key West the day of the Hemingway 5K race. After the ride, they would arrive in time to register for the race and run the 3.1 mile course. Afterwards they would drink a couple of beers at the  race party and hit Duval Street until 4 AM. The Tradition continues.

The ride will start at 9 AM at Sombrero Beach. We will have a fully SAG supported vehicle tailing the riders for the duration of the Ride. There will be 4 scheduled stops located on the South Side of 7 Mile Bridge, Kikis Sandbar and Grill, Baby’s Coffee and the Southernmost Marker . We are charging $75 for the SAG support only. Our group is staying overnight in Key West and doing the 5K run. If you want a ride back with bikes to Marathon the following morning, it’s an additional $75 fee. We are doing a bike rental special of $25 for a road bike for this event.

U.S. Coast Guard Cutter Ingham Maritime Museum

Race Participants Receive 10% OFF Admission to U.S. Coast Guard Cutter Ingham Ship Museum!
Show your Bib or entry receipt (5K or Paddleboard) to receive 10% OFF! 


Stop by the U.S. Coast Guard Cutter Ingham Ship Museum at Truman Waterfront to take a tour of the most decorated Coast Guard ship in history! And enjoy Happy Hour on Friday & Saturday nights — a spectacular view of Key West’s prized sunsets!
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