Sailfish & Short Stories: Summer Heats Up with Hemingway Days in Key West

Sailfish & Short Stories: Summer Heats Up with Hemingway Days in Key West

Florida Keys Road Trip Weekly • July 18, 2025

🕰️ A Little History: How Hemingway Days Began

It all started in 1981 with a stroke of genius from Michael Whalton, then-day manager at Sloppy Joe’s—Ernest Hemingway’s favorite bar. Inspired by LA’s parody contests, Whalton launched a small birthday tribute: a short-story contest, beard-off, street fair, beer guzzling—and thus, Hemingway Days was born.

The "look-alike" contest has since become a global pastime—ironically honoring an author never one for pomp, but deeply in love with Key West's sun, surf, and sailfish.

🔥 Hemingway Days Takeover Edition

This ain’t your average summer vacation.
Next week, Key West throws on a beard, grabs a daiquiri, and channels the literary legend himself.

It’s Hemingway Days.
And it’s gonna be five glorious days of typewriters, tall tales, tight lines, wild parades, and some truly epic facial hair.

📅 July 23–27
📍 All over Old Town Key West
🎟️ Full schedule + ticket info

🧔‍♂️ WEDNESDAY, JULY 23

🍻 Meet the Papas @ Sloppy Joe’s | 6–7 PM
Beards. Booze. Bragging rights.
Kick it off with past champs and Papa hopefuls as the look-alike legends gather for cocktails and competition.

☕ THURSDAY, JULY 24

Coffee & Donuts with the Papas @ Southernmost Pint | 9–10 AM
Beards + bear claws = island bliss.

Pre-Contest Happy Hour @ Hemingway Social Club | 5–7 PM
Loosen those nerves and those mustaches.

Look-Alike Contest: Round 1 @ Sloppy Joe’s | 6:30 PM
It's the Super Bowl of facial hair. Come early—this place packs out.

🎣 FRIDAY, JULY 25

Papa Hemingway Fish-Off @ Conch Republic Docks | 1 PM
Catch-and-release with Cuban yo-yos. Yeah, it’s as old-school as it sounds.

Look-Alike Contest: Round 2 @ Sloppy Joe’s | 6:30 PM
Fewer beards. Higher stakes. More mojitos.

🎉 SATURDAY, JULY 26

Caribbean Street Fair on Duval | 10 AM–10 PM
Live music, rum drinks, seafood, and souvenirs you’ll question later.

Photos with the Papas & Bulls @ Greene Street | Noon
Running of the Bulls | 1 PM
(Picture this: Hemingway look-alikes being chased down Duval by fake bulls. It’s chaos. It’s tradition. It’s Key West.)

Hemingway 5K Sunset Run @ Southernmost Beach Café | 7:30 PM
Because Papa would’ve wanted it sweaty and slightly competitive.

🎂 SUNDAY, JULY 27

Papa’s Birthday Bash @ Sloppy Joe’s | 9 AM–1 PM
Cake, photos, and Bloody Marys for all.

Beach N’ Beer Mile @ Southernmost Beach | Noon
Four laps. Four beers. One unforgettable Sunday Funday.

Pool Party @ Blue Flamingo Resort | 3–6 PM
Close out the weekend island-style, with flamingo floaties and frozen drinks.

🎣 BEYOND PAPA

Marlin Tournament @ Perry Hotel & Marina | July 23–26
Big fish, bigger egos, and one heck of a weigh-in.

Lorian Hemingway Short Story Contest
Aspiring writers, this is your moment.

Hemingway Home Tours @ 907 Whitehead St
Six-toed cats. A backyard pool. And the desk where the legend worked his magic.

🌆 DUVAL STREET GOES OFF

• Rum bars, drag shows, street performers, and conch fritters for days

• Sloppy Joe’s, Rum Bar, Chart Room—Papa-approved and party-tested

• Literary landmarks tucked between bars and butterflies

🧭 PRO TIPS FOR THE WEEK

• Book Now: Hotels near Duval sell out fast.

• Hydrate Often: Mojitos don’t count.

• Dress Smart: SPF, comfy shoes, and something breezy.

• Wake Up Early: Mornings are cooler, calmer, and way better for photos.

📸 SHARE YOUR WEEK

Tag us with #US1KeysHemingway — your beard, your fish, your festival fun might just land you in next week’s edition.

✍️ YOUR HEMINGWAY MANTRA

"By day we chase sailfish. By night, we chase Papa. And both leave us breathless."

🎉 See you in the madness,
Brian & The Florida Keys Road Trip Crew
#StayLost #LiveFree