Key West Summer Festivals 2026: A Planning Guide to July, August & September
Five festivals. Three months. From Independence Day straight through Labor Day, Key West runs one long celebration, right when the rest of the world thinks the island slows down. July through September is filled with a love of lime, lobster, and rum, plus Papa Hemingway’s birthday and a Labor Day tribute to Jimmy Buffett. America’s 250th lands right in the middle of it all.
And a lot of it happens right here at the beach. Southernmost Beach Resort hosts a piece of nearly every one, including the World Famous Pie Eating Championship on the Fourth, the Lobsterfest and Rum Fest send-offs, and the Cheeseburger Beach Battle and Jimmy Buffett tribute concert.
While each festival features dozens of events across the island, visit the official websites linked at the end of each section for complete schedules and details.
Here’s what’s happening, when, and how to time your visit.
Photo credit: Carol Tedesco
2026 Summer Festivals at a Glance
July 1–5: Key Lime Festival
July 22–26: Hemingway Days
Aug 5–9: Key West Lobsterfest
Aug 10–16: Key West Rum Fest
Sept 3–7: Just a Few Friends (Jimmy Buffett Tribute)
Together, Southernmost Beach Resort and sister property The Marker Key West Harbor Resort host and sponsor events across four of these five celebrations. For the full year, check out our 2026 Key West festivals guide.
July in Key West: Key Lime & Papa
Key Lime Festival (July 1–5)
The Key Lime Festival and America’s 250th come together over one unforgettable holiday weekend.
Photo credit: Virginia Wark, Key Lime Festival
The week opens Wednesday, July 1 at The Avalon with a kickoff party and a pageant for the title of Key Lime Emperor or Empress. From there it moves fast: Hot Wheels races at Mary Ellen’s, a 5-Alarm pie built with habanero cream at the historic firehouse museum, sunset cocktails on a Coast Guard cutter with the USCG Band, a Sloppy Joe’s fundraiser where donations decide which local personality takes a pie to the face.
Saturday, July 4th starts with a 5K at sunrise, then the main event in the afternoon: the World Famous Pie Eating Championship, held at the resort’s own Southernmost Beach Café at 1:30 pm (nine-inch pie, hands behind back). As the sun sets, fireworks light up the island. Will you watch from land or sea?
Photo credit: Carol Tedesco.
The festival closes Sunday, July 5th at The Marker with the Reggae Concert Pool Party & Key Lime Cocktail Bartender Battle, presented by J.F. Haden’s Craft Liqueurs, 2 to 5 pm. Local bartenders compete with one liqueur. The crowd is the judge.
See what else is happening during the Key Lime Festival.
Hemingway Days (July 22–26)
More than a hundred bearded Hemingway look-alikes converge on Sloppy Joe’s in late July. They take it seriously. So does Key West. Don’t be surprised if you’re walking the streets saying “I just saw Papa” over and over again.
Hemingway lived and wrote in Key West for most of the 1930s, turning out some of his best work in the studio behind 907 Whitehead Street. The Look-Alike Contest runs at Sloppy Joe’s, his old hangout at 201 Duval, with the final on Saturday, July 25. The Key West Marlin Tournament runs July 22–25, with $50,000 in prizes.
Saturday, part of Duval Street closes for the Caribbean Street Fair and the Running of the Bulls, where Papas chase wooden bulls on wheels rather than the real thing. Pamplona it is not.
Photo credit: The Florida Keys & Key West
Read our blog and learn more about Hemingway and his cats in Key West.
See what else is happening during Hemingway Days.
August in Key West: Lobster & Rum
Key West Lobsterfest (Aug 5–9)
Florida’s spiny lobster season opens August 6th, and Key West has been celebrating it for 28 years. Five days of reverence for a bug that survives perfectly well in butter: Wednesday’s kickoff at Rick’s & Durty Harry’s, then Thursday’s Lobster Boil at the Porter Mansion.
Friday afternoon, head over to The Marker for The Lobsterfest Pool Party from 3 to 6 on August 7. The Marker Pool Bar is also the Lobsterfest Pub Crawl check-in from 3 to 7:30 before the crawl heads down Duval at 8.
Saturday’s Street Fair takes over Duval with Just George, Fried Newt, Jordan Oaks, and headliners The Durtbags. Sunday wraps at Southernmost Beach Resort with the farewell pool party from 1-4 and the Lobster Roll Eating Contest. Proceeds support the Key West High School Scholarship Fund.
See what else is happening during Key West Lobsterfest.
Key West Rum Fest (Aug 10–16)
Rum Fest treats rum the way wine festivals treat wine: with experts, context, and a lot of fun. A full week of tastings, sunset sails, dinners, and pool parties builds around National Rum Day on August 16.
Thursday, August 13: Marsh House Rum Pool Party at The Marker, 1 to 4 pm, with live music by the Jack Snacks Trio.
Friday, August 14th: Nauti Beach Rum Mojito Party at Southernmost Beach Resort at the Shores Pool, 3 to 6, with live music by Sharese.
Saturday, August 15th: Grand Tasting at Key West Theater, 2:30 to 5:30, featuring 30+ rum brands from around the world.
Sunday, August 16th: Going Away Pool Party by Captain Morgan at Southernmost Beach Resort, 1 to 4 at the Pineapple Pool.
Proceeds benefit MARC House.
See what else is happening during Rum Fest Key West.
September in Key West: A Labor Day Tribute
Just a Few Friends (Sept 3–7)
In its third year, Just a Few Friends is a five-day celebration of Key West’s favorite son, honoring Jimmy Buffett in the place he so loved and is so missed. Get ready for five days of music, storytelling, and an island celebration like no other.
Photo credit: Mark Hedden/Florida Keys News Bureau
Thursday opens at Southernmost on the Beach with the Cheeseburger Beach Battle and Tribute Concert from 5 PM to 8 PM. Jimmy Buffett tribute band Gypsies in the Palace hits the stage at 5:30 PM. Friday is a Duval Street Party with Gary & the Landsharks, recreating the 1998 Parrothead street party. Saturday afternoon’s Milagro Margarita Bar Stroll begins at The Marker, with check-in from 11 AM to 2 PM to pick up your event t-shirt and tasting guide. The Wheeland Brothers play at Sunset Pier that night.
Sunday is the heart of it. The Pool Party at The Marker runs 1 to 4, then the Second Line Memorial Parade heads down Duval at 5 and into the Party in the Park at Truman Waterfront, where Howard Livingston, Will Kimbrough, and Mac McAnally take the stage.
Cayman & the Mango Men close it out Monday at Sunset Pier. Event badges support Reef Relief, the Bahama Village Music Program, and Key West High School scholarships.
Read and learn more about Jimmy Buffett’s Key West: Places, Stories, and Songs.
See what else is happening during Just A Few Friends Key West.
As Jimmy Buffett put it, “If there’s a heaven for me, I’m sure it has a beach attached to it.” We saved you a spot on ours. #somolife