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

Saturday, July 24, 2021


Saturday, July 24, 2021 – RACE DAY!

3:00 pm – 6pm: Pre-Race Sip, Shop, & a Show at Sea, Key West Watersports Company, 720 B Caroline Street

  • Get ready for the Hemingway 5K & Paddleboard Race Key West style at Sea, Key West! The locally owned and operated watersports store will be celebrating with apps, local beer (it’ll help you race faster!), and a movie, plus an exclusive 20% discount for all race participants with proof of race entry. Shop paddle boards, SCUBA dive, free dive, spearfish, snorkel equipment and more and take advantage of free delivery anywhere in Key West. RSVP HERE

3:00 pm – 7 pm: Race Registration Booth

  • Location:  Truman Waterfront Park, Foot of Southard Street

5:00 pm: Start of Paddle Board Race

  • Location: Southernmost Beach, 1405 Duval Street

7:30 pm: Start of 5K Run/Walk

  • Location: Truman Waterfront Park, Foot of Southard Street

9:00 pm – 11:00 pm: Post Race Specials, More details COMING!

  • Location: Southernmost Beach Café, Schooner Wharf Bar and Old Town Tavern

Sunday, July 25, 9am – 9:45am

Post Race Recovery Yoga with Salute to the Sol Yoga, Truman Waterfront

  • Celebrate your accomplishment while easing sore muscles from the race with an all-levels yoga recovery session. This class is free to all participants (just show your bib or medal!) and located at the beautiful Truman Waterfront downtown, Key West with plenty of parking. Don’t forget to BYOM (bring your own mat)! RSVP HERE

Key West First Legal Rum Distillery

  • (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.)

2021 Race Shirt & Medal Unveiled!

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 to keywesthalfmarathon@gmail.com 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.)

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!

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/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 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.

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