Hemingway 5k Sunset Run

Hemingway sleeping polydactyl cat key west

The Hemingway 5k Sunset Run is an out-and-back course that starts at the Southernmost Point at Whitehead and South streets in Key West, Florida. It was 90° with 59% humidity at the 7:30 PM start. I felt absolutely lethargic due to the heat but once the gun went off I was ok.

Runners head down Whitehead Street to the turnaround point at the Mel Fisher Maritime Museum.  The course makes a short loop out towards Zachary State Park before finishing back at the Southernmost Point.

Hemingway 5k Sunset Run, Paddle-board & Century

If you are feeling super ambitious you can complete the trifecta; the Hemingway 5k Sunset Run, the Hemingway paddle-board 3-mile race, and the Hemingway Century Tour.  The bike ride starts at 7:30 AM, on race day, at the Key Largo Bike shop in Tavernier, Florida.

Post-race refreshments include beer from the Islamorada beer company and rum, with an awards party at the Southernmost Beach Cafe. Race entrants receive a high-quality v-neck shirt with a Hemingway Maritime design, as well as, a race medal.  Key West is a walkable city so you don’t need to worry about race parking.  Alternatively, you can hop on the free Duval bus service that runs every 15-30 minutes between 6 AM and midnight.

Places to Eat & Stay

Sloppy Joe's Bar, Key West, Florida
Sloppy Joe’s Bar, Key West, Florida © 2018 Susan M Hall
Hemingway sleeping polydactyl cat key west
“Joe DiMaggio”, one of the Hemingway polydactyl cats has 24 toes total. There are currently 57 cats at the Earnest Hemingway House and Museum. Polydactyl cats are considered good luck in maritime culture. © 2018 Susan M Hall

I arrived a couple of days before the 5k race and visited the Hemingway House and Museum to see the polydactyl (six-toed) cats, as well as, Sloppy Joe’s Bar for the Hemingway Look-Alike Contest. My favorite dinner was the “grouperwich” and Kalik Gold beer at B.O.’s Fish Wagon and Kermit’s Key Lime Pie on a stick, hand-dipped in chocolate.

Key West Bed & Breakfast
Key West Bed & Breakfast © 2018 Susan M Hall

Key West Bed & Breakfast is centrally located at 415 William Street in Key West, Florida within walking distance of Sloppy Joe’s Bar, the Hemingway House and Museum, and the Hemingway 5k Sunset Run starting line. 

If I had it to do over again I’d probably fly into Key West instead of Fort Lauderdale. It’s about a 4-hour car trip to Key West.  Overall it’s a great getaway for a long weekend.


Susan M Hall is an American long-distance runner with a goal to run a 10k in all 193 UN recognized countries plus the two permanent non-member observer states of Palestine & the Holy See.

On her radar are the Košice Peace Half Marathon ☮️ Kosice, Slovakia, the Istanbul 15k 🇹🇷, Istanbul, Turkey the Beirut Half Marathon, Beirut, Lebanon, the Pyramids Half Marathon, Giza, Egypt & the Quantum Nicosia Half Marathon, Nicosia, Cyprus.

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