Key West celebrates Hemingway Days in July! Come for Papa — stay for all the action on this storied

Visit Key West in July, and you might think you’ve stepped into a novel. An Ernest Hemingway novel, that is. That’s when the island celebrates its most famous resident each year with a lively tribute. This year, from July 23–27, Key West will be swept up in Hemingway Days, an annual event that’s equal parts quirky and cultural. It’s the perfect excuse for a sun-soaked July vacation with Historic Key West Vacation Rentals providing your home base. Through our curated collection of properties, you can live like a local — and sleep like a legend.

An author and an island forever linked

Ernest Hemingway didn’t just visit Key West — he lived it, breathed it and helped define it. Already famous after publishing “The Sun Also Rises,” Hemingway moved to Key West in 1928 with his wife Pauline and spent most of the 1930s on the island. He lived in a now-famous home on Whitehead Street and wrote some of his greatest works, including “To Have and Have Not” (his only novel set in the United States, and inspired by his life in Key West), “Green Hills of Africa,” and short stories such as “The Snows of Kilimanjaro” and “The Short Happy Life of Francis Macomber.”

When he wasn’t writing in his home studio, Hemingway found pleasure in deep-sea fishing, sparring in the boxing ring, or hanging out at Sloppy Joe’s Bar — still an iconic local favorite. Hemingway’s larger-than-life persona helped shape the free-spirited, artistic culture that makes Key West so unique.

A grand party that began with Sloppy Joe’s

Hemingway Days began when the Hemingway Look-Alike Society, founded by a former resident, hosted a promotional event in 1981 for Sloppy Joe’s Bar. This local institution opened in 1933, at the end of prohibition, when a well-known rumrunner opened a legitimate business, and Hemingway joined the party crowd here. It’s said that characters in “To Have and Have Not” are based on some of the real-life characters who frequented the bar where Hemingway became a popular regular.

Today, Sloppy Joe’s resides at 201 Duval Street and claims the title of one of the most famous bars in the country. You won’t want to miss this iconic local attraction, billed as the best party in Key West.

When you visit Key West this July, you can’t help but join in the 2025 Hemingway Days celebration, which includes events like the Papa Look-Alike Contest at the bar, where bearded men from around the world gather to channel their inner Hemingway and compete for the coveted title. You’ll also enjoy the prestigious Lorian Hemingway Short Story Competition, supporting emerging writers; literary panels with authors and Hemingway scholars; special exhibits and daily tours at the famous Ernest Hemingway Home & Museum; the Key West Marlin Tournament; a Caribbean Street Fair, showcasing local artisans and cuisine; and a Papa Birthday Bash, featuring Hemingway’s signature drinks and a rum bar stroll through town.

Be a part of any or all of these events, and more, to honor this local legend during your July vacation in Key West! Don’t miss the chance to walk in Hemingway’s footsteps and hear all the stories behind the stories.

In addition, at Historic Key West Vacation Rentals, our special guest services team of local experts are ready to help book exciting excursions like fishing charters, boat tours and many more island adventures.

Vacation in Hemingway-inspired style

After a full day of festivities, you’ll want a relaxing space that feels just as storied as the island. Here’s a short list of what awaits you in Key West with Historic Key West Vacation Rentals.

• Dreaming on Duval —  This 5BR, 4.5BA knockout with a fabulous private pool is just steps from Sloppy Joe’s and all the action you can handle in Key West.
• Three Arches in Paradise — Live like a true local during your extended stay in this spacious, serene and stylish home with a private pool.
• Hibiscus Cottage — Our 2BR, 2BA historic Conch-style home offering cozy charm amid a lush tropical garden is ideal for couples.
• Chavez House — Old Town charm meets modern comfort in this unique and lovingly restored traditional island eyebrow house.

Historic Key West Vacation Rentals offers an extensive portfolio of homes. Book now to experience the island’s July Hemingway Days celebration. There’s plenty more to explore!

Don’t wait — book your July escape now

Hemingway Days is one of Key West’s most beloved festivals, and vacation rentals fill up quickly. Book your stay now with Historic Key West Vacation Rentals and immerse yourself in the stories, attractions and celebrations that Papa himself would have found inspiring. Have questions or need help finding the perfect vacation rental home? Visit our About Us page or speak to our friendly team directly. Come for Papa — and stay for the history, the sunshine and the unforgettable magic of a Key West vacation.

Published on Wednesday, April 16, 2025