If you’re planning a trip to Key West this summer, there are plenty of fun things to see and do during your time here. In addition to the typical attractions here all summer long, you’ll also have several entertaining Key West events to attend. One of the most popular celebrations is the Key West Hemingway Days! Guests in our Key West vacation rentals love to engage in the Hemingway Days activities to make memories with their loved ones and have a truly one-of-a-kind experience in this particular locale. Here’s everything you need to know before you go!
History of Hemingway Days
Even if you’re not a massive fan of classic literature, there’s a good chance you’re familiar with Ernest Hemingway. If you don’t recognize the name, you might recognize some of his famous works, such as A Farewell to Arms, For Whom the Bell Tolls, The Sun Also Rises, and The Old Man and the Sea. Hemingway lived in Key West starting in the 1930s, and now, Hemingway Days serve to celebrate the author’s life and acknowledge the many aspects of the area that he loved during his time here.
Hemingway Days began in the 1980s and has been a staple of the community ever since. Each year, locals and visitors alike come out to learn more about Hemingway and what he liked to do while he lived in Key West.
You can learn some fascinating history, witness incredible events, and meet with locals during this fun annual festival. Once you experience Hemingway Days for yourself, you’ll quickly understand why it’s considered one of Key West’s best things to do.
Hemingway’s Estate in Key West
During your stay in our Key West rentals, visit Hemingway’s Estate. This destination is a landmark of the area even when the celebrations aren’t going on, but paying a visit will give you more appreciation for the festivities. This Estate is where Hemingway penned his famous works To Have and Have Not and Death in the Afternoon.
The home was initially built in 1851, and when the Hemingways arrived, it needed some profound love and care. The couple (Ernest and his wife Pauline) started remodeling the properties in the early 1930s, transforming them into the landmark that it is today. Even though Ernest and Pauline divorced in 1940, the author continued to visit the area throughout his life until he died by suicide in 1961.
Guests are welcome into the museum on the Estate daily from 9 a.m. to 5 p.m., but be aware that admission is cash only. As you wander the grounds, you’ll witness the massive swimming pool (the first in-ground pool in Key West!), lush gardens, and even a group of more than 60 cats! Hemingway himself owned a six-toed cat, so the Estate keeps dozens of these cats on the property today to honor the author.
Key West Hemingway Days Events
In 2022, Hemingway Days will be celebrated from July 19 to 24. Admission prices or ticket requirements may vary by event. This year will be the 41st annual event, so it’s sure to be one to remember!
First, come out to experience the exciting Running of the Bulls. Held at Sloppy Joe’s Bar and the Lookalike Contest (more on that in a moment), this event is simply one to witness. Ernest Hemingway lookalikes head down Duval Street pushing fake bulls as they go, racing to see who can get to the finish line first.
If you want to stay active during your trip, sign up for the 5K and Paddleboard Race! You’ll begin the race at the Southernmost Beach starting at 5:30 p.m. Competitors will start by paddle boarding a three miles long course. Then, they’ll get out of the water and begin running a 5K at 7:30 p.m. This section of the race runs from the Southernmost Point of the Continental U.S. throughout Old Town Key West, even passing the famous Ernest Hemingway Home and Museum itself.
One of the most popular things during Hemingway Days is the Hemingway Lookalike Contest. This event is held at Sloppy Joe’s Bar, a destination that Hemingway himself used to frequent when he lived here almost a century ago. More than 100 participants grow out their beards and try to emulate the iconic author for this contest, with two rounds of preliminary competition before the competitive final round.
Finally, don’t miss a chance to watch or participate in the Key West Marlin Tournament. In 2021, this tournament paid out a whopping $250,000! The tournament will run from July 20 to 23 and guarantees $50,000 in cash prizes! During the tournament, boats will sail out to catch as many fish as possible, including blue and white marlin, spearfish, and sailfish. This event is truly the epitome of Key West fishing.
To enter, each boat can have a captain, two anglers, and four social privileges for a $2,100 entry fee. You can have unlimited anglers in your boat, but be aware that additional anglers will pay $200 apiece to fish, and other social privileges will pay $150 apiece. If you’re interested, register fast since this tournament is only open to the first 75 boats to sign up!
Plan Your Key West Vacation
If you’re looking for an unforgettable vacation, Key West is the perfect destination for you! Start planning your favorite vacation yet and book your Key West vacation home today!
Your Key West Vacation Home
From deep-sea fishing in Key West to exploring the area’s fascinating backstory, Hemingway Days is an event with a little something for everyone. If you want to be present for the entire festival and truly make the most of your time here, you’ll want to book one of our Key West waterfront rentals. That way, you can be within walking distance of the festivities and enjoy everything that Key West offers.
Key West Vacation Homes is proud to offer a vast selection of properties for any group on any budget. You can select a rental property in the middle of town, settle down on the beach, or stay near the water in our Key West rentals with a dock. No matter which rental you select, you can rest assured that you’ll have access to high-speed Internet, flat-screen TVs, fully stocked kitchens, spacious living areas, and plenty of outdoor space.
On top of that, you also have our friendly staff by your side to answer any questions you might have here on your trip. They can recommend the best things to do in the area, tell you about some fun day trips nearby, or explain the many features of your rental. We spare no expense to make sure that your trip is simply unforgettable. Thanks to our unique properties and impeccable customer service, we’re proud to say that guests return to us year after year for their annual vacations.
If you plan to come down to Florida for the 41st Annual Hemingway Days, contact us today to get started booking your rental. Then, start growing out your beard or taking some practice runs to gear up for the festivities!
