Hosted by Just a Few Friends, Conch Republic Seafood Company, Fury and Reef Relief, this is the first official event kicking off the Labor Day celebration! Keep Key West Beautiful and Plogging the Keys sponsor regular Friday morning cleanups, and you're invited to take part in this important effort. Our partners at Reef Relief are joining us too, reinforcing our shared commitment to keeping Key West clean and promoting eco-tourism practices that protect our island home.

Join us for one hour picking up litter at Greene Street, Simonton Street, and other areas of Old Town. Meet at the bar on the corner of Greene and Elizabeth to pick up your parking pass (if needed), vest, gloves, bucket, and picker! We’ll work our way to Simonton Beach and end back at the Conch Republic Seafood Company—known lovingly by locals as the Conch Farm.

One hour makes a huge difference! Start your festival weekend by working side-by-side with Key West locals and visitors to help keep our community beautiful.

Join city, county, and state leaders along with local celebrities, officers from the Conch Republic, and the Key West High School Marching Band at the pocket park in front of Shrimp Boat Sound Studios at the historic Key West Seaport. Together, we'll witness the official reading of the City of Key West’s proclamation declaring Jimmy Buffett Day.

This outdoor welcome ceremony officially kicks off the Just a Few Friends Labor Day Weekend Celebration—marking the start of a heartfelt tribute to the music, life, and legacy of Key West’s favorite son.

Take a 90-minute guided walking tour through some of the most celebrated haunts in Key West, frequented by our favorite son over his expansive history here.

You'll visit the outside of his beloved music studio—where you’re welcome to leave a memento or sticker—and hear colorful stories about his pirate life in the Keys.

This laid-back stroll covers iconic sights, little-known secrets, and special moments tied to the music and spirit that shaped an island legend.

Yes, I am a Pirate

Author Lecture, Guest Discussion Panel & Book Signing

Phil Clark was immortalized in song by Jimmy Buffett, but 'A Pirate Looks at Forty' belies his privileged past. Following exhaustive research by author Scott Atwell, stories of Clark’s life emerge in fascinating detail about a New York sophisticate who sailed off to the lower latitudes of the globe, where pirates once roamed, and reinvented himself on an island. Not in a good way, but a memorable one. If we looked closely enough, scattered clues would have led us to the story's conclusion, like an 'X' on the map. This is the true tale of the Pirate, Phillips Clark.

About the presenter: Native Conch Scott Atwell turned an all-Jimmy Buffett radio program into a popular book that explains the origins of the singer’s most beloved songs.

About the panelists: Following the presentation, Atwell will be joined on stage by writer and Phil's former girlfriend, Carol Shaughnessy, along with Lower Keys fishing guide Chris Robinson and Clark's son flip McCririck.

CAROL SHAUGHNESSY

The last of Phil Clark’s “younger women”, she was engaged to marry the Pirate when he slipped out of Key West for the last time. She went on to serve as editor of Jimmy Buffett’s Coconut Telegraph.

CHRIS ROBINSON

Landed a job tending bar at the Chart Room after Phil Clark sailed off to the Bahamas with the women who would later become Robinson's wife. They lived right below Jimmy Buffett in the Waddell Street compound next to Louie’s backyard, and today Chris is a renowned flats guide.

FLIP McCRIRICK

First-born child of Phillips Clark, a namesake son who did not learn of his father’s connection to Jimmy Buffett until ten years ago. Unlike his dad, McCririck found his occupation in the 20th century as a celebrated sports photographer.

Gypsies In The Palace is Nashville’s go-to Jimmy Buffett tribute band for true Parrotheads who know there’s more to the story than just the greatest hits.

When was the last time you heard “Everybody’s Got a Cousin in Miami,” “Cuban Crime of Passion,” or “Last Mango in Paris” played live?

We dig deep into Buffett’s catalog to bring the hidden gems to life—celebrating his music, his legacy, and the laid-back lifestyle with a crowd that knows exactly what it means to be a Pirate looking at forty.

Come to Hogs Breath raise a glass with Gypsies In The Palace—where the vibe is easy, the stories run deep, and every show feels like a toast to the man himself.

2 shows - Friday, August 29 & Saturday, August 30, 4:30pm - 8:30pm

Wind down or gear up with daily happy hour at the legendary Chart Room Bar—one of the most storied watering holes in Key West. Join your friends (and meet new ones) for drink specials exclusively for JAFF badge holders, plus free popcorn, peanuts, and all the laid-back charm you’d expect from this historic hideaway. Enjoy trop rock music each evening from the very spot where a young singer-songwriter once sat with a guitar and a dream—long before he became a household name. The Chart Room isn't just a bar—it’s part of the story. And happy hour here is your front-row seat to the past and present.

Cheeseburger Beach Battle presented by Landshark

Who makes the best hamburger with cheese in a tropical place? You be the judge at our lively beachside competition!

Throw down a few Landshark Beers while you sample tropical cheeseburgers from nine of Key West’s favorite restaurants and caterers to the backdrop of live island tunes and beachside vibes.

These chefs will be competing for your vote:

🍔 Dorada Restaurant at the Casa Marina

🍔 Four Marlins at the Reach

🍔 Great Events Catering

🍔 Key West First Legal Rum Distillery

🍔 Mac’s Place

🍔 Perla Cuban Cuisine at La Concha Key West

🍔 Southernmost Beach Cafe at Southernmost Beach Resort

🍔 Surly Siren Saloon

🍔 Yellow Fin Bar & Kitchen at Oceans Edge Resort

The event kicks off at 5 PM with bars and food available. Burger tasting and voting run from 5 PM to 7 PM, and the Margaritas in Paradise, Jimmy Buffett tribute band, will take the stage at 5:30 PM for a lively set of classic hits, creating the perfect beach party soundtrack.

Tasting tickets are limited to 300 and are expected to sell out quickly!

Set sail on The Sandie Cat for an unforgettable evening at sea.

As the sun dips below the horizon painting the sky with brilliant hues, indulge in an unlimited open well bar featuring rum-runners, margaritas, mixed drinks, draft beer, wine, champagne, and soft drinks.

Savor a selection of delicious appetizers as you glide through the crystal-clear tropical waters. Feel the rhythm of the islands with live music from one of Key West’s top trop rock entertainers, setting the perfect soundtrack for your sunset cruise.

With a tropical drink in hand and the ocean breeze in your hair, dance the evening away and experience the legendary beauty of a Key West sunset.

This is more than just a trip—it’s a memory you’ll treasure.

Settle in for an evening under the stars with a special outdoor screening of Tales From Margaritavision.

This rare compilation brings together music videos, live performances, and behind-the-scenes footage curated by singer-songwriter Jimmy Buffett and producers Mike Ramos and Stan Kellam. It’s a musical time capsule blending beloved tunes with documentary-style glimpses into a life lived on island time.

Your hosts for the evening are The Pint and Blast Beer Company—a small, family-owned brewpub where every beer has a backstory and every dish is gluten-free and made with care.

Blast Beer was founded in 1990 by Purdue University student Tadd Maudlin, whose passion for brewing eventually led him and his wife Lindsay on an epic sailing adventure around the globe. After brewing in Mexico and traveling through the Caribbean, Europe, and Africa, they landed in Key West and brought their love of craft beer and hospitality with them.

Come for the movie, stay for the beer, and enjoy a cozy, one-of-a-kind night celebrating music, adventure, and community.