Key West’s Hemingway Days (2026)
It’s one of the most fun times to be in Key West. Hemingway Days is an annual festival honoring one of the island’s most famous former residents and renowned literary icon, Ernest Hemingway. Held every year during the week of Hemingway’s birthday, it’s a time when the rum flows freely, tall tales are told, and everywhere you look, you’ll spot a white beard on a man going by the name “Papa” for the day.
Whether you’re a fan of Hemingway’s works or just enjoy the overall fun and quirkiness of a Key West festival (who doesn’t?), Hemingway Days is always a great time.
Go ahead and pack your bags, book that tropical vacation villa of your dreams, and grab your copy of Old Man and the Sea. Here’s everything you need to know about attending Hemingway Days Key West 2026!
Hemingway Days 2026
- When: July 21st – 26th, 2026
- Where: Festival headquarters are at Sloppy Joe’s Bar, located at 201 Duval Street, but events are also held at various locations throughout Key West
- Cost: Most festivities are free, but some special events require tickets
- Event Schedule and Tickets: keywestlookalikes.com/schedule
2026 marks the 45th year of Key West’s Hemingway Days, and it’s shaping up to be one of the best yet, with 6 days of food, rum, music, literary readings, fishing tournaments, Ernest Hemingway memorabilia, and of course, the famous Hemingway Look-Alike Contest and Running of the Bulls (don’t worry, they’re plastic).
Things to Do at Hemingway Days
You’ll find fun Hemingway-themed food, drink, and festivities every day of the festival, but there are a few standout things that most people who come to Hemingway Days don’t want to miss.
Walk Through History at the Hemingway Home
While you can tour the Hemingway Home and Museum anytime you’re in Key West, visiting during Hemingway Days always feels extra special. Maybe it’s fellow Hemingway fans you’ll meet, maybe it’s the Hemingway look-alikes you’re bound to spot, or perhaps it’s seeing the famous six-toed cats, descendants of Hemingway’s original feline friend, Snow White (our favorite thing about the Hemingway Home).
Either way, this iconic landmark is full of history, and what better time to walk the halls where Ernest Hemingway lived and learn about his life and legacy than during the Hemingway Days celebration!
Stroll the Caribbean Street Fair
Celebrating “Papa’s” love of Caribbean food, music, art, and culture, the Caribbean street fair is held right in the heart of Key West on Duval Street and showcases local artisans and vendors. Stroll the street fair and enjoy tasty Caribbean bites and sips from local restaurants, shop for unique Caribbean and Hemingway-themed art, crafts, memorabilia, and more.
Watch the Hemingway Look-Alike Contest
A crowd favorite and can’t miss when visiting Key West during Hemingway Days, the Hemingway Look-Alike Contest brings in Ernest Hemingway look-alikes from across the country to compete for the crown of “Papa” of the year. In true Hemingway spirit, there will be lots of storytelling, laughter, and of course, rum.
Think you might have what it takes to be the next Papa Hemingway? Enter the contest and join in on the fun!
Run into the Sunset at the Hemingway 5k (July 25-26th, 2026)
A 5k like no other, this one’s at night(ish) and features an epic after-party on the beach with live music, food, rum tastings, and more. Hosted by the same folks from the famous Key West Half Marathon and Runfest race series, the Hemingway 5K Sunset Run is a great way to get a little exercise while having lots of fun.
Listen to Papa’s Tales
Honoring two of Hemingway’s great loves, the written word and rum, Papa’s Tales Storytelling Competition is fittingly held at Papa’s Pilar Distillery and features a lineup of spoken-word stories of three minutes or less. Sit back, relax, sip on some rum cocktails, and listen to tales inspired by one of the greatest literary figures of all time.
Reel in a Big Catch, Just Like Papa
If you’re an angler at heart like Hemingway, you can enter the Key West Marlin Tournament and have the chance to reel in a big catch and compete for cash prizes. Or if you prefer to keep your hands dry, you can watch the Papa Hemingway Look-Alike Fish Off.
Held at the Conch Republic Seafood Company. Watch as Hemingway look-alikes cast traditional Cuban yo-yos into the water for a friendly, catch-and-release competition.
Catch a Special Screening of The Old Man and the Sea
Watch as one of Hemingway’s most famous, Nobel Prize-winning works comes to life during a special screening of The Old Man and the Sea. This 1958 classic stars Spencer Tracy as Santiago, the Cuban fisherman famous for battling it out with a massive marlin in one of Hemingway’s greatest tales. Williams Hall typically hosts a special screening during Hemingway Days. It’s a great time for book and film lovers alike.
Snap Some Pics with the Papas
While there are lots of great photo ops and meet and greets during Hemingway Days, Sloppy Joe’s Bar hosts one of the largest gatherings of Hemingway look-alikes and spirited fans for “Photos with Papas.” Typically held right before the Running of the Bulls, if you were hoping to meet some “Papas” and snap that iconic Insta-worthy pic of a sea of white beards and red berets, this is the time!
Watch the Running of the Bulls
Inspired by Hemingway’s love of Spain, but with a quirky Key West twist, the Running of the Bulls brings together all the “Papas” from around Key West dressed in their Pamplona best, accompanied by plastic bulls for a dash down Duval Street. Don’t worry, there are no real bulls involved. Although, in true Key West fashion, you may spot the occasional rooster joining in on the fun.
Attend Papa’s Birthday Bash
What’s a birthday celebration without a party and cake? Celebrate Papa Hemingway’s birthday alongside fellow Hemingway enthusiasts at the iconic Sloppy Joe’s Bar.
Complete with birthday cake, Bloody Marys, photo ops with the winner of the Hemingway look-alike contest, and much more. Typically held on the last day of the festival, it’s the perfect way to close out your visit.
Hemingway Days FAQs
Do you need tickets for Hemingway Days in Key West?
Many of the Hemingway Days festivities are free and do not require tickets. However, if you’re planning to participate in the 5K, the fishing tournament, and/or other special events, tickets may be required. More information on special events and links to purchase tickets can be found here.
Is Hemingway Days in Key West family-friendly?
Overall, Hemingway Days can be family-friendly, especially the daytime events. However, since some events are held at local bars and feature loud music, a boisterous atmosphere, and alcohol, parents are encouraged to check the schedule to see which events might be best suited for their children to attend.
Where should I stay for Hemingway Days in Key West?
Key West can get pretty packed for Hemingway Days, which can mean busier than usual hotels, crowded pools, and late-night noise. To make the most of your trip, we recommend a relaxing stay in a vacation rental. Book your stay with Vacation Homes of Key West and enjoy a private, spacious vacation home with amenities like pools and hot tubs, and options within walking distance to the festivities.
What’s the best way to get around Key West during Hemingway Days?
Most festivities take place downtown around Duval Street, so if you’re staying nearby, walking will be your best bet. If you do need transportation, we recommend utilizing local taxis, rideshare services, or trolleys, as parking can be limited and some areas will have street closures.
Ready to Party Like Papa?
You’re sure to have a great time at Hemingway Days, and in addition to all the festival fun, the island has so much to offer by way of beautiful beaches, fun activities, historic sites to explore, great shopping, fantastic food, and so much more. It’s easy to see why Ernest Hemingway loved this place so much.
Enjoy the best of Key West by booking your Hemingway Days stay with VHKW. You’ll enjoy a relaxing stay, close to all the festivities, while enjoying premium amenities like fully furnished homes, private pools and hot tubs, and so much more!
