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.

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.

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.

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.

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.

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.

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).

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.

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.

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.

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.

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 clips and behind the scene stories from Shrimp Boat Sound: Echoes from the Edge at Williams Hall.

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.

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.

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.

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.

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.

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.

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

Presented by Hogfish Bar & Grill

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.

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.

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.