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 22, 2023 – RACE DAY!
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 23, 2023
12:00 pm – 3:00 pm Hemingway Rum Stroll – More details to come.
2023 Race Shirt & Medal Unveiled!
T-shirt designed using Taylor Hale Paintings.
Meet the Artist:
Taylor Hale is a native Floridian who draws inspiration from a lifetime on the water in his island hometown of Key Largo, Florida. He earned a BFA from the Rhode Island School of Design in 2009.
Taylor is driven by the constant transformations of the sky and sea—exploring what happens as these powerful natural forces interact. Within his work, he captures movement and stillness, familiarity and the unknown, peace and unrest. In each oil painting, he seeks to create a window to connect to another world.
He loves meeting other cloud lovers and has found that an admiration for the ever-changing sky is something that can connect people from all walks of life. He invites his viewers to bring their unique perspectives to each piece and explore where the art takes them!
When he’s not painting, he enjoys spending time in nature, seeing live music, and being with his wife and daughters.
In 2023 Taylor looks forward to opening The Hale Gallery in Islamorada!
Connect with Taylor on Instagram and Facebook (@taylorhalepaintings) and at www.taylorhalepaintings.com
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.)
Featured by Runner’s World as one of the Best 5Ks to Run this Summer.
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.
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.
