34th Anniversary
Hemingway 5K Sunset Run & Paddleboard Race

Saturday, July 22, 2023


Saturday, July 22, 2023 – RACE DAY!

3:00 pm – 7 pm: Race Registration Booth

  • Location:  Outside Southernmost Beach Cafe, 1405 Duval Street


Saturday, July 22, packet pick up at 3 pm SHARP.

    1. Check in for your shirt at Southernmost Beach Cafe, 1405 Duval street on the beach (without your board)
    2. Drive, with your board, to Higgs Beach, 1000 Atlantic Avenue (1/4 mile away – see map below)
    3. Check in for your race number with your board with Lazy Dog
    4. After the race, pack your board and go back to Southernmost Beach Cafe for the Awards Party and enjoy Islamorada Beer and Papa’s Pilar Rum!

5:30 pm: Start of Paddle Board Race – NEW LOCATION!!!

  • New Location: Higgs Beach, 1000 Atlantic Blvd, Key West, FL 33040

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 by Island Steel Drum Player Ivan Bertie!!

  • Location:  Outside Southernmost Beach Cafe, 1405 Duval Street

Results will be posted race evening www.keywesthalfmarathon.com and our Facebook page.


2023 Race Shirt & Medal Unveiled!

T-shirt designed using Taylor Hale Paintings.

Sunday, July 23, 2023

12:00 pm – 4:00 pm Hemingway Rum Stroll Sponsored By Papa’s Pilar Rum

  • Featuring delicious Papa’s Pilar Rum Libation Special at each location!
    Starting at the Hemingway Rum Distillery, 201 Simonton Street. This beautiful location is really cool!
    1. Hemingway Distillery – Makers of Papa’s Pilar Rum
    2. First Flight, 301 Whitehead St
    3. The Saint, 417 Eaton St
    4. Kaya, 628 Rear Duval St
    5. Tipsy Rooster, 1325 Simonton Street
    6. Rams Head Southernmost, 804 Whitehead Street
    Must be over 21, Entry Fee: $45 includes Custom Rum Stroll Race Shirt, rooster wrap and Hat!.

12:00 pm Key West Beach N’ Beer Mile! 4 Loops, 4 Beers from Islamorada Beer Co., Custom Shirt, Rooster Wrap and Hat! Price: $45. Race is NOT TIMED!

  • Location:  Outside Southernmost Beach Cafe, 1405 Duval Street
  • Prizes awarded for:

1. Best Team Spirit
2. Best Dressed
3. Least Dressed

3:00 pm – 6:00 pm  Pool Party at Rum Row! Drinks specials by Papa’s Pilar Rum and DJ Louie M! Rum Row – 3824 N Roosevelt Blvd.

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

Meet Van Bertie, (Van the Pan Man):

Van Bertie, (Van the Pan Man), a multi-talented musician was born on the Caribbean island of  St. Kitts. His musical journey has taken him across the globe, captivating audiences at diverse events and venues. He was immersed in music from a young age, inspired by his father’s piano playing and his older brothers’ musical talents. Van’s passion for music led him to pick up the guitar at the tender age of five, and over the years, Van expanded his instrumental repertoire. He picked up the steel drums about 12 years ago due to the popularity of Caribbean music and also plays the flute.

He started a four-piece band, traveling through the Caribbean, playing in places like Saint Croix and Saint Thomas. Later, he performed as a solo artist, showcasing Caribbean music, reggae, calypso, R&B, and top 40 hits in Africa, Canada, and New York.

Now settled in Florida, Van specializes in performing at weddings, corporate events, major hotels, and various gigs. He currently plays in a five-piece reggae band, as well as a blues band. One of the reggae band’s favorite gigs is the Annual Bob Marley Birthday Tribute at the Green Parrot in Key West. With a diverse musical background and a passion for performing, Van Bertie continues to leave his mark on the music scene, both locally and internationally.

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!


  • $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!


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

Mellow Ventures

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


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 – Website
  • Mellow Ventures   305-745-3874

The Annual Hemingway Bicycle Tour

July 23rd, 2022

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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