EVENT DETAILS
34th Anniversary
Hemingway 5K Sunset Run & Paddleboard Race
Saturday, July 22, 2023
HEMINGWAY 5K SUNSET RUN & PADDLEBOARD PRESENTED BY PAPA’S PILAR RUM
RACE SCHEDULE
Saturday, July 23, 2022 – RACE DAY!
11:00 am – 2:00 pm: Sea, Key West 720B Caroline Street. Fuel up before the race with free healthy snacks at our locally owned watersports equipment store. In addition to snacks, all race participants will receive a 20% discount on any store purchases.
3:00 pm – 7 pm: Race Registration Booth
- Location: Outside Southermost Beach Resort, 1405 Duval Street
5:30 pm: Start of Paddle Board Race
- Location: Southernmost Beach, 1405 Duval Street
7:30 pm: Start of 5K Run/Walk
- Location: Southernmost Point
8:00 pm – 10 pm The Awards/Beach Party featuring Tastings of Papa’s Pilar Rum, Islamorada Beer and Food, raffles and entertainment!
- Location: Outside Southermost Beach Cafe, 1405 Duval Street
Sunday, July 24, 2022
12:00 pm – 3:00 pm Hemingway Rum Stroll
Sunday, July 24
Key West First Legal Rum Distillery
- 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.)
Sunday, July 24th | Noon-3:00 pm
First Stop: Hemingway’s Library at Papa’s Pilar Rum Distillery
and then visit these bars in any order :
Tattoos & Scars, The Backyard Bar, Viva Argentinian Steakhouse, Southernmost Beach Cafe,
Party at: Rams Head Southernmost starting at 2:30 pm!
RAFFLE INCLUDES TRIP TO THE GALLEY BAY RESORT AND SPA IN ANTIGUA!!!
- $45pp includes one drink at each stop (choice of Papa’s Pilar rum drink, domestic draft/bottle, or any well drink. Hemingway Rum Distillery will serve rum special)
- Only 75 spots are available on the Rum Stroll
- All Rum Stroll participants receive a Rooster wrap & party at Rams Head
- The first 48 who pick up their rum stroll drink tickets and wristband will receive a complimentary souvenir miniature Papa’s Pilar Rum bottle
- All Rum Stroll participants also receive a free Papa’s Pilar Rum Drink card for the Hemingway Rum Distillery!
YOU MUST PICK UP YOUR DRINK TICKETS, WRISTBAND, ETC. AT THE HEMINGWAY 5K SUNSET RUN REGISTRATION ON SATURDAY, JULY 23, 3:00 PM – 7:00 PM
Proceeds will benefit the College of the Florida Keys Youth Swim Program & Key West Sunrise Rotary.
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, (7/21-7/25). The answers will be emailed to you by Monday morning.
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.)
Runners, walkers and paddleboard enthusiasts can test their skills and celebrate Ernest Hemingway’s sporting lifestyle Saturday, July 23, 2022 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.
Thank You to our Sponsors
Thank You to our Charity Partner
Paddleboard Rentals for the Hemingway Paddleboard Race
*You must have a Personal Flotation Device with you during the race
Lazy Dog Outfitters
Mellow Ventures
305-745-3874
Paddleboard rental info:
*1 hour dockside $25
*2 hour dockside $35
*4 hour take away $45
*Full day $65
*Weekly rates available
mellowventureskeywest.com
facebook.com/mellowventureskeywest
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
305-741-7490
Paddleboard Rental Companies
*You must have a Personal Flotation Device with you during the race.
- Lazy Dog – Website
- Java Cat 305-294-7245
- Mellow Ventures 305-745-3874
- Sea, Key West 305-741-7490
- Sunset Watersports 305-296-2554
The Annual Hemingway Bicycle Tour
July 23rd, 2022
Produced by: Key Largo Bike and Adventure Tours
305-395-1551
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.
