Join city, county, and state leaders, local personalities, and representatives of the Conch Republic at the pocket park in front of Shrimp Boat Sound Studios in the historic Key West Seaport for the official reading of the City of Key West’s proclamation declaring Jimmy Buffett Day.

Set at the very studio where so much of his music and story took shape, this outdoor ceremony serves as the official kickoff to Just a Few Friends—marking the beginning of a weekend dedicated to celebrating the life, music, and legacy of Key West’s favorite son.

Singer-songwriter Cliff Cody will perform his tribute song “Rest in Paradise,” written and recorded in honor of Jimmy Buffett following his passing. Recorded at Shrimp Boat Sound itself, the song reflects the spirit of the island and the enduring connection between the place, the music, and the man.

Simple, heartfelt, and rooted in place, this is a moment to gather, reflect, and begin the weekend together.

[Promo photo: Lucy Buffett accepts the proclamation from Key West Vice Mayor Donnie Lee at the 2025 celebration. Photo by Nick Doll]

Painting Paradise: A Guided Plein Air Experience

Slow down, step outside, and see Key West through a different lens.

As part of Just a Few Friends, we’re offering intimate guided plein air sessions at iconic island locations that played a role in the creative life and inspiration behind Key West’s music, storytelling, and laid-back way of being. Whether you’re an experienced artist or simply enjoy sketching, this relaxed outdoor experience invites you to capture the architecture, light, and atmosphere that define the island—your way.

Each two-hour session includes a brief introduction to the site, light guidance from a local instructor on composition and capturing Key West’s distinctive light, and plenty of time to create your own interpretation. There are no rules on what to paint—just the freedom to follow what inspires you.

Session Details

Each session is $25 and includes paper and a board for painting on. Participants may bring their own materials or add on a basic watercolor kit. Artists are welcome to work in any medium, including watercolor, acrylic, oil, colored pencil, ink, or mixed media.

Session One: Shrimp Boat Sound

Friday, September 4, 2026 · 8:00–10:00 AM

Paint at the historic studio that played an important role in shaping the island’s musical legacy. You might focus on the building itself, the quiet charm of Lazy Way, or any detail along the historic waterfront. Morning light and architectural lines create the perfect setting for a focused study in color and shadow.

Session Two: Louie’s Backyard

Saturday, September 5, 2026 · 9:00–11:00 AM

Set along the water just steps from where Jimmy once lived, Louie’s Backyard was quite literally part of his backyard—and a place he spent time enjoying the very lifestyle this festival celebrates. From the house and iconic bar to Dog Beach or the sweeping ocean views, there’s no shortage of inspiration—just choose your perspective and make it your own.

Guests may register for one session or both. Space is limited to 20 participants per session to maintain a relaxed and personal experience.

Participants are invited to display their finished work during the “Painting Paradise” pop-up exhibit at Party in the Park.

Artists may choose to:

Retrieve their artwork at the end of Party in the Park

Donate their piece to be sold or auctioned, with proceeds benefiting festival charities

A Judge’s Choice and People’s Choice will be awarded from submitted works. Winners will receive a ribbon, $50 cash prize, and badges to next year’s festival.

Sponsored by Keys Framing & Art Supplies

Hosted by Just a Few Friends, Conch Republic Seafood Company, Fury, and Reef Relief, this community-driven cleanup is a chance to give back while you’re in town for the weekend. Keep Key West Beautiful and Plogging the Keys sponsor regular Friday morning cleanups, and you’re invited to take part in this important effort—supporting Reef Relief’s ongoing work to protect our local marine environment.

Participants are welcome to head out on their own or team up as we cover Greene Street, Simonton Street, the Historic Seaport, and surrounding 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 wrap up back at the Conch Republic Seafood Company—known to locals as the Conch Farm—where participants will be welcomed with complimentary juice, coffee, and pastries.

We’ll also gather for a group photo, and all participants will receive a special sticker for their souvenir charity Event Badge as a thank you for doing your part to help keep Key West—and this little part of the world—a better place.

One hour makes a meaningful difference. Spend a little time side-by-side with locals and fellow visitors helping care for the place we all came to enjoy.

Start your morning with a relaxed island breakfast, whether you’re coming from the Harborside Cleanup at the Historic Waterfront, heading to the City Proclamation Ceremony honoring Jimmy Buffett—or simply looking for a great place to gather and ease into the day.

Hosted by the Concrete Public Seafood Company, you’ll enjoy great food paired with waterfront views that capture the easy rhythm of Key West. The laid-back setting makes it just as much about the atmosphere as it is the meal.

Settle in with a spread of eggs, sausage, bacon, pancakes, and fresh fruit, with Bloody Marys and mimosas available to raise a glass to clean shores, island spirit, and the man who made Key West his home.

Swap stories with fellow friends or simply take it all in—it’s an easy, satisfying way to start the day and settle into the rhythm of a meaningful day in paradise.

Take a 90-minute guided walking tour through the heart of Old Town, beginning at his beloved recording studio—an unassuming space that played a pivotal role in shaping the sound, stories, and spirit that grew out of Key West.

Here, you’re invited to leave a sticker or small memento and take a moment to connect with a place that holds deep meaning for fans. From there, your guide will lead you through a thoughtfully curated route of iconic landmarks, hidden corners, and longtime local haunts tied to his life on the island.

Along the way, you’ll hear colorful stories of the early days—when Key West was a haven for artists, misfits, and free spirits—and how that environment helped influence a style of music and a way of life that would resonate far beyond the island.

Blending history, storytelling, and local insight, this laid-back stroll offers a deeper look at the people, places, and moments that helped define an era.

More than a walking tour, it’s a chance to experience the spirit of Key West through the lens of the music, the lifestyle, and the community that made it all possible.

Start your day on the water with fellow Just a Few Friends guests on a 4.5-hour sail through the quiet beauty of the Key West backcountry.

Aboard a shallow-draft schooner, you’ll glide into places most visitors never see—paddling through peaceful mangrove channels, snorkeling in calm, crystal-clear waters, or simply stretching out on deck and enjoying the breeze. With a small group of 20 or fewer, there’s plenty of space to relax, connect, and move at your own pace.

No experience? No problem. The crew provides all equipment and a quick, easy briefing so you can jump right in—whether it’s your first time or your hundredth.

Fresh fruit and healthy snacks are served onboard, along with water and soft drinks throughout the trip. After the water activities, enjoy beer and wine as you sail back in—an easy, social way to experience the natural side of Key West before the music and festivities pick up.

Stop by Festival Headquarters anytime during the week to pick up badges, get event information, meet up with other Friends, and grab a refreshing pina colada (badge holders get $1 off).

There’s the soundtrack everyone knows—and then there are the songs that tell the deeper story.

Gypsies in the Palace, Nashville’s go-to Jimmy Buffett tribute band, leans into the full catalog—bringing out the deep cuts, the fan favorites, and the moments that longtime listeners recognize the second the first chord hits.

You might hear “Cuban Crime of Passion,” “Last Mango in Paris,” or one of those songs you haven’t thought about in years—but somehow still know every word.

It’s not just a show—it’s a gathering of people who understand the lifestyle, the storytelling, and the connection that lives beyond the hits.

Join us at Hogs Breath, grab a drink, and settle into a set where the vibe is easy, the music runs deep, and the crowd feels like old friends.

📅 Friday · 12:00–4:00 PM

📅 Saturday · 4:30–8:30 PM

The Chart Room at the Pier House is one of Key West’s most legendary gathering spots—a place where history, character, and community all come together in a way that feels untouched by time.

This is where it all began. Long before the big stages, a young musician played here for drinks and tips and met his future wife, Jane, inside this very room. That origin story is part of what gives the Chart Room its unmistakable energy—one that still resonates with those who step inside.

Tucked away from the bustle of Duval Street, the space is small, dimly lit, and wrapped in warm wood with a classic nautical feel. It’s a quiet escape from the outside world, where conversations flow easily and the pace naturally slows down. Look closely and you’ll find layers of local lore—including the bar top itself, where a few legendary regulars, like treasure hunter Mel Fisher, are memorialized in a uniquely Key West tradition.

During Just a Few Friends, the Chart Room becomes a natural gathering place throughout the week. Open daily from 1:00 PM to 1:00 AM, it’s a come-and-go hangout where you can always find familiar faces, strike up a conversation, or simply settle in and take it all in.

There’s no agenda here—just pull up a stool, grab a drink, and let the room do the rest. Complimentary popcorn, peanuts, and the famous Chart Dogs add to the easygoing atmosphere, making it just as inviting for a quick stop as it is for a longer stay.

Authentic, unfiltered, and full of stories, the Chart Room captures the spirit of Key West—and the sense of connection at the heart of Just a Few Friends.

There are many places to eat lunch in Key West. But there’s only ONE place to have lunch with a legend. Join us for Key West’s only all-inclusive dine-in musical experience, revisiting the glory days of 1970s Key West when a young songwriter named Jimmy called this island home.

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume as the man himself in a show blending live music, storytelling, humor, and of course...Cheeseburgers! Enjoy a journey back in time to a place where artists and misfits lived the eclectic Bohemian dream, and our favorite "grandson of a sailor" roamed the land.

Part lunch theater, part tribute concert, and part educational adventure, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the songs, spirit, and the island where the legend began. This show is a MUST-SEE for all Buffett fans, music enthusiasts, or anyone looking for Key West’s most entertaining lunch experience.

Your ALL-INCLUSIVE ticket to this performance includes one cheeseburger with chips and one drink from the bar’s lunch menu. Additional beverages and drink specials will be available for purchase from the bar.

Showtime is 12:30pm, and doors open at 12:00pm (NOON). We request that you arrive no later than 12:15pm to ensure seating and drink service before the show begins.

Disclaimer: This is an independent tribute performance and is not affiliated with, endorsed by, or sponsored by Jimmy Buffett, Margaritaville Holdings LLC, or the estate of Jimmy Buffett. All references are made in the spirit of celebration and artistic homage.

Join your fellow Just a Few Friends guests for a classic Key West experience as you head out to snorkel North America’s only living coral reef aboard a state-of-the-art Fury catamaran. This is one of the island’s most iconic on-the-water adventures—and a perfect way to mix, mingle, and connect with other “friends” while exploring the crystal-clear waters surrounding Key West.

After a scenic sail, dive in to discover vibrant coral formations, tropical fish, and the natural beauty of the reef, with all gear and guidance provided for every comfort level. Throughout the trip, enjoy complimentary sodas and water, with beer, wine, and of course margaritas served after snorkeling as you relax on the spacious sundeck or shaded lounge. It’s an easy, social, and unforgettable way to experience the water that defines Key West.

Step into the story behind one of Key West’s most iconic creative landmarks with a special director’s presentation of Shrimp Boat Sound: Echoes from the Edge at Williams Hall.

This feature documentary explores the legendary waterfront studio built at the southernmost edge of the United States—a place that helped shape the sound and spirit of Gulf & Western, blending country, rock, and island influence into something entirely its own. Through rare archival footage and interviews with artists, producers, and those who lived it, the film captures how this unlikely studio became both a creative refuge and a catalyst for a genre.

This is not a film screening. Instead, director Michael J. Kirk will lead an interactive presentation featuring select scenes and behind-the-scenes footage, offering insight into the making of the film, the stories behind the interviews, and the historical significance of Shrimp Boat Sound. With the film not yet released, this is a rare early look at a project that’s poised to make waves as it hits the film festival circuit.

Joined by special guests, the conversation unfolds in real time, creating a deeper, more personal connection to both the film and the legacy it documents.

Hosted by the Key West Art & Historical Society and moderated by Dr. Cori Convertito, this is a unique opportunity to experience the film as it’s being shaped—and to be part of the conversation preserving a meaningful piece of Key West history.

Join us Friday for a special Just a Few Friends presentation of A Pirate Looks Back, the Key West Jimmy Buffett tribute show, created exclusively for Ultimate Friend guests. Set in an intimate venue where every seat offers a fantastic view, this is the full, immersive experience—live music, storytelling, humor, and a journey back to 1970s Key West—shared with a room full of fellow “friends.”

Acclaimed musician, actor, and Buffett historian Caleb Hogan returns in character, capturing the spirit and sound of those early island days. For this performance, he’ll incorporate a few special moments and surprises designed just for this group, making it a one-of-a-kind experience you won’t find in the regular show. Your ticket includes a complimentary margarita to get things started, with a cash bar available throughout.

No food service, no distractions—just a chance to settle in, share a drink with fellow “friends,” and enjoy a unique take on one of Key West’s most entertaining musical tributes.

Learn more about Chris here ==> https://chrislauber.substack.com/

Tales from the Chart Room — Pull up a stool in one of Key West’s most legendary watering holes for Tales from the Chart Room. Hosted by Carol Shaughnessy—the first writer of the Coconut Telegraph, a longtime member of the Margaritaville team, and former partner of Chart Room icon Phil Clark—each 30+ minute session features a different special guest sharing firsthand stories from the Key West moments that inspired the songs and shaped the lifestyle.

Carol isn’t just a host—she was there. From the early days of the Chart Room to the characters, music, and mischief that defined the era, she knows where the stories begin—and where a few of them are buried. Through a relaxed, guided conversation, she draws out inside insights and colorful memories from friends, musicians, and locals who lived it. Stay tuned for specific daily topics and very special guests.

There’s no stage or formal production—just authentic storytelling in an intimate setting, with the occasional audience question if the moment calls for it. This is the history you won’t find written down, shared in the room where so much of it actually happened.

Sessions will also stream live, so grab your souvenir charity Event Badge for virtual access to all the nostalgia, all the stories, and all the good stuff.

A special photography installation will feature a curated collection of Chris Lauber’s vintage concert photographs of Jimmy Buffett, captured during the early years and reflecting a remarkable personal journey that began in the 1970s. These images are more than memorabilia—they are firsthand visual documents of a formative era, offering an intimate look at the energy, spirit, and evolution of an artist whose connection to Key West became part of music history.

Chris will be a featured guest at Tales from the Chart Room, where he’ll join a moderated conversation to share how these photographs came about, the experiences behind them, and why they remain such an important part of telling the story. Following that session, the photography exhibit will formally open in the lobby outside the Chart Room, where guests will have a chance to view the collection and meet Chris.

The exhibit will remain on display throughout the festival, giving attendees an opportunity all weekend long to experience this rare visual tribute to Jimmy Buffett’s early years through the lens of someone who was there.

Step into a piece of Parrot Head history 🌴🎶 as Duval Street comes alive for a special recreation of the legendary 1998 Meeting of the Minds street concert.

The evening kicks off with Caleb Hogan, whose acoustic set channels the storytelling, humor, and early spirit of Key West that helped define the music and the lifestyle.

Channeling the look and spirit of ’70s Buffett, Caleb will also host the first annual Bubba Look-Alike Showdown, presented by Hogfish Bar and Grill. Contestants bring their best looks, moves, and personality to the stage—and the crowd decides the winner. It’s part tribute, part competition, and all in good fun as the audience becomes part of the show.

At 7:30 PM, Gary & the Landsharks take over Duval Street, delivering the high-energy, sing-along set that brings it all home. This nostalgic throwback captures the raw, unfiltered energy of those iconic Key West nights when the music took over the street and the crowd became part of the show.

Break out your vintage Parrot Head gear, throw on those old-school tees, and come ready to sing every word 🍹 This is one of those rare moments where past and present collide—bringing longtime fans and first-timers together in the heart of it all.

While the concert is free and open to all, Ultimate Friend and Best Friend VIP badge holders will have priority upfront access near the stage—putting them right in the center of the action.

✨ Free and open to the public

🍹 Come early · Stay late · Sing loud

Brought to you in part by Milagro, Sloppy Joe’s, Irish Kevin’s, and the Tourist Development Council.

Keep It Going… Hog’s Breath Saloon After Party

Once the Duval Street concert wraps, this is where the crowd heads next.

Hog’s Breath Saloon—one of Key West’s most legendary live music spots—sets the tone for a full-throttle Friday night as the weekend hits its stride. Expect a packed house, cold drinks, and that unmistakable mix of locals and visitors all in the same place, keeping things rolling.

Live music features Gulfstream, a feel-good band rooted in the easygoing spirit of Florida’s Gulf Coast. Founded and fronted by singer-songwriter Andy Mauerman, the group blends modern country, classic rock, and coastal Americana into a smooth, beachy sound that feels right at home in Key West. Their sets move effortlessly from laid-back grooves to crowd favorites, with songs from Kenny Chesney, Zac Brown Band, the Eagles, Zach Bryan—and of course, plenty of Jimmy Buffett woven throughout.

It’s the kind of music that keeps the energy up without losing that relaxed, coastal feel—perfect for a Friday night that’s just getting started.

No cover. Cash bar.

Join the Key West Parrot Head Club and settle in for an evening under the stars as we screen Parrot Heads – The Essential Jimmy Buffett Documentary. This fan-favorite film dives into the incredible community inspired by Jimmy Buffett’s music and laid-back lifestyle, exploring how one man’s songs built a worldwide family of devoted, flip-flop-wearing, island-loving fans.

Learn the story behind the phenomenon as told through rare interviews, concert footage, and the voices of Parrot Heads themselves.

The Pint and Blast Beer Company will be pouring small-batch craft brews and offering rotating gluten-free menu favorites all night. Beer and wine are available for purchase, and beach chairs are provided for a cozy, casual Key West evening under the stars.

Come toast to the music, the memories, and the community that keeps the island spirit alive.

Climb aboard the Coconut Telegraph Trolley Tour for an unforgettable narrated journey through the Key West landmarks that shaped the music and the lifestyle.

Hosted by JAFF co-founder Sean Krikorian and longtime Key West insider Carol Shaughnessy—the original writer of the Coconut Telegraph—this experience is grounded in real history, personal connection, and the stories behind the stories.

This comprehensive island tour goes beyond the walking version, covering more ground while diving into the places, characters, and moments that helped define an era.

Roll past the bars, streets, and hidden corners that inspired legendary songs, including his former home in New Town, a stop at Fausto’s Food Palace for a chocolate milk (a nod to his famous cure for a long night), Dog Beach and Louie’s Backyard—just steps from where he once lived—and out to Stock Island for a stop and a drink at the infamous locals’ watering hole, Hogfish Bar & Grill.

Along the way, you’ll hear firsthand stories, insider perspectives, and the lasting influence of island life that shaped both the music and the culture.

Created exclusively for Just a Few Friends, this is a one-of-a-kind experience you won’t find any other time or place—an authentic look at the Key West that inspired it all.

Presented by Hogfish Bar & Grill

Friday Night · Duval Street Party · Just a Few Friends Festival

As part of the historic recreation of the 1998 Meeting of the Minds concert on Duval Street—featuring Gary & the Landsharks—the stage will turn into a search for the island’s best Bubba.

If you’ve ever been told you look like the troubadour — any age, any era — this is your moment.

The Bubba Look-Alike Showdown invites contestants to step into the spotlight and channel the look, attitude, and presence of Key West’s favorite son. Whether it’s the early pirate days, the mustached storyteller, or the laid-back island legend, we’re looking for the one who brings it to life best.

Hosted by local Jimmy look-alike and Comedy Club lunch show host Caleb Hogan, contestants will take the stage one by one, introduce themselves, and then pick up a guitar provided on stage. From there, a random, well-known Jimmy Buffett song will kick in—and it’s on. Each contestant will have to lip sync, perform, and embody the part in front of a live audience.

A panel of esteemed local representatives will narrow the field down to three finalists. From there, the crowd takes over—the winner will be decided by audience vote via QR code, making this a true people’s choice moment.

The champion will take home:

• $1,000 cash prize

• The Golden Coconut Trophy

• Festival bragging rights

Presented by Hogfish Bar & Grill, a true Stock Island institution and longtime favorite of Jimmy Buffett himself. Owner Bobby Mongelli, a close friend of Jimmy’s, helped create the kind of place Buffett loved most—unpretentious, local, and real. It’s also where one of his most iconic late-life Key West photos was taken, sitting at a picnic table, right at home.

Pre-registration is strongly encouraged to guarantee a spot.

Walk-up entries will only be accepted if space is available.

Think you’ve got what it takes?

Come prepared.