Your Ultimate Key West Weekend Getaway Guide: July 23–27, 2025

Get ready to dive into the sun-soaked, quirky paradise of Key West for an unforgettable weekend starting tomorrow, Wednesday, July 23, 2025! This tropical island is pulling out all the stops with the Hemingway Days festival stealing the show, alongside fishing tournaments, street fairs, and sunset vibes that’ll make your Instagram pop. Here’s your snappy guide to squeezing every ounce of fun out of your Key West getaway!

Wednesday, July 23: Kick Off with Papa and Marlin Madness

• Hemingway Days Begins! The island transforms into a tribute to Ernest Hemingway, the literary legend who called Key West home. Head to Sloppy Joe’s Bar (201 Duval St.) at 6:30 p.m. for the Hemingway Look-Alike Contest. Watch bearded, jolly “Papas” battle it out to be crowned the ultimate Hemingway doppelgänger. Free to spectate, and the energy is electric!

• Key West Marlin Tournament (July 23–26): Anglers are reeling in big fish and bigger prizes ($260,000 total, including $50,000 for marlin!). Even if you’re not fishing, swing by the docks to feel the buzz. Check keywestmarlin.com for locations.

• Sunset Celebration at Mallory Square: Starting around 6:30 p.m., this nightly bash brings jugglers, musicians, and artisans to the waterfront. Grab a mojito, snap a sunset pic, and soak in the Key West magic. Free!

Pro Tip: Pack light, breathable clothes—it’s hot and humid. Stay hydrated and slather on sunscreen!

Thursday, July 24: More Papa, Markets, and Sunset Vibes

• Hemingway Look-Alike Contest, Round Two: Back at Sloppy Joe’s at 6:30 p.m., the Papa hopefuls keep the party going. Grab a seat early; it’s a hoot! Free entry.

• Key West Farmers Market: From 2:00 p.m. to 7:00 p.m. at Truman Waterfront, score fresh mangoes, homemade treats, and quirky crafts. Food trucks and live music make it a chill afternoon vibe.

• Marlin Tournament Continues: The fishing frenzy rolls on—check out the action at the docks or join the after-fishing parties.

• Sunset Celebration: Another evening of fire-eaters and sunset glory at Mallory Square around 6:30 p.m.. You can’t get enough of this!

Pro Tip: Bring cash for the farmers market—some vendors don’t take cards. Pair your market finds with a sunset stroll for the perfect evening.

Friday, July 25: Papa Heats Up and Fishing Intensifies

• Hemingway Look-Alike Contest, Final Prelims: The last round before the big finale hits Sloppy Joe’s at 6:30 p.m.. The crowd’s rowdy, the beards are epic, and the drinks are flowing. Free to watch!

• Key West Marlin Tournament: Day three means more fishing and dockside excitement. Cheer on the anglers as they chase that $50,000 marlin prize.

• Sunset Celebration: Keep the tradition alive at Mallory Square around 6:30 p.m.. Try a conch fritter from a nearby vendor for a true Key West bite.

Pro Tip: Book a table at a Duval Street spot like The Green Parrot for post-event drinks and live music to keep the night going.

Saturday, July 26: Bulls, Runs, and Papa’s Big Moment

• Running of the Bulls: At 1:00 p.m. on Greene Street outside Sloppy Joe’s, Hemingway look-alikes parade with fake bulls in a hilarious nod to Pamplona. It’s absurd, it’s free, and it’s peak Key West weirdness—don’t miss it!

• Hemingway Look-Alike Contest Finale: The main event at Sloppy Joe’s at 6:30 p.m. crowns the new “Papa.” Expect a packed house, wild cheers, and serious Hemingway swagger. Free to join the fun.

• Hemingway 5K Sunset Run & Paddleboard Race: Lace up or grab a paddle for this 7:30 p.m. race starting at the Southernmost Point Buoy. Register ($45–$85) from 3:00 p.m. to 7:00 p.m. at Southernmost Beach Cafe (1405 Duval St.). Stick around for the beach party with live music, Papa’s Pilar Rum, Islamorada Brewery tastings, and raffles. Not a runner? Come for the party!

• Caribbean Street Fair: Duval Street turns into a festive hub with vendors, food, and Hemingway-inspired flair. Stroll, shop, and eat your way through the day.

• Marlin Tournament Finale: Celebrate the winners at the final weigh-ins and awards. Check keywestmarlin.com for details.

• Sunset Celebration: Cap the day at Mallory Square around 6:30 p.m. with more performers and that unbeatable Key West sunset.

Pro Tip: Wear comfy shoes for the street fair and 5K party. Bring a reusable water bottle to stay cool while hopping between events.

Sunday, July 27: Farewell to Hemingway and Farmyard Fun

• Hemingway Days Wrap-Up: The festival closes with literary readings and a Papa Birthday Bash celebrating Hemingway’s 126th birthday. Check hemingwaydays.com for times and locations. It’s a great way to soak up some literary vibes.

• Sheriff’s Animal Farm Open House: From 1:00 p.m. to 3:00 p.m. at Stock Island Detention Center (5501 College Rd.), meet capybaras, sloths, and goats. It’s free, kid-friendly, and a quirky way to end your weekend. Donations of cash or fresh produce are appreciated.

• Sunset Celebration: One last dose of Mallory Square magic around 6:30 p.m. to send you off with a smile.

Pro Tip: Visit the Ernest Hemingway Home and Museum on Sunday morning to see where Papa lived and meet the famous six-toed cats. Book tickets early at hemingwayhome.com.

Make It Epic

• Where to Eat: Grab conch fritters at Conch Republic Seafood Company, key lime pie at Kermit’s, or fresh seafood at Eaton Street Seafood Market.

• Where to Stay: Check keywest.com for hotels or cozy B&Bs like The Mermaid & The Alligator. Book ASAP—Hemingway Days fills up fast!

• Getting Around: Rent a bike or scooter to zip around the island. Parking’s tight, and walking Duval Street is half the fun.

• Stay Updated: Visit hemingwaydays.com, keywest.com, or keywesttourist.com for last-minute event details.

This weekend, Key West is serving up sun, sea, and a whole lot of Hemingway swagger. Pack your flip-flops, channel your inner Papa, and make this getaway one for the books!