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.

The exhibit is 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.

6.5 hour excursion on a skipjack schooner for a full day of fun and sun on the water. Enjoy plenty of time snorkeling as well as kayaking around one of the mangrove islands and weather permitting, a stop at an island with a beach or a sandbar while taking in all the beauty of our Florida Keys Ecosystem.

Between activities, you'll enjoy a full lunch while you relax and take in some sailing. Beer, wine, water, sodas, and snacks are also provided - tin cup optional!

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.

This may become one of the most talked-about moments of the entire weekend.

The experience begins with a chef-curated beachfront brunch at the Pier House from 10:00–10:45 AM, complete with a Bloody Mary or mimosa overlooking the water in the relaxed style that defines Key West mornings.

Guests will then move into the legendary Chart Room Bar.

Long before stadium tours and sold-out amphitheaters, this tiny wood-paneled hideaway inside the Pier House was where Jimmy Buffett found his footing in Key West. He played for drinks and tips here in the early days, surrounded by fishermen, wreckers, writers, bartenders, and the colorful cast of characters who helped shape both his music and the island mythology that followed. The room remains largely unchanged — a living piece of Key West history and one of the most iconic spaces connected to Buffett’s story.

Inside this intimate setting, acclaimed songwriter and longtime collaborator Will Kimbrough will perform a rare up-close set filled with music, storytelling, and personal reflections. Kimbrough co-wrote “Bubbles Up,” the final Jimmy Buffett song released posthumously, and has spent decades creating music alongside some of the most respected names in Americana and roots music.

This will not be a traditional concert.

It’s a rare opportunity to sit inside the room where so much of the story began and experience the music and memories in a way that simply cannot happen from a stage.

All guests will receive a limited-edition commemorative keepsake created exclusively for this experience — a unique memento from an unforgettable Key West moment shared with just a few friends.

Attendance is extremely limited and expected to sell out quickly.

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).

Do you have the perfect pencil-thin mustache—or something a little more… Bubba?

Join Just a Few Friends, the legendary Chart Room, and Beards and Brews for the 3rd Annual Mustache Contest—a lighthearted tribute to one of the most iconic looks (and songs) in island lore.

Whether your ‘stache is real, ridiculous, or completely made up, there’s a category for you—and plenty of laughs along the way.

🏆 Categories

— Best Look-Alike

— Best Pencil-Thin Mustache

— Best Creative Mustache

🎖️ Category winners advance to People’s Choice Best of Show, where one grand champion will take home an unforgettable prize package—including Key West Express tickets, a two-night stay at the Pier House, dinner at One Duval, a limited-edition bottle of First Legal Agave Spirits, and ultimate bragging rights.

📍 Set in the iconic Chart Room—where the stories are real and the history runs deep—this is one of those only-in-Key-West moments you don’t want to miss.

Registration: noon to 12:30 pm

Contest: 12:30 pm to 1:30 pm

A Bit About the ‘Stache

The pencil mustache rose to popularity in the 1930s and ’40s, worn by Hollywood icons like Clark Gable and Errol Flynn as a symbol of suave style. It found new life in 1974 with “Pencil Thin Mustache,” a nostalgic, tongue-in-cheek tribute to a bygone era—celebrating the characters, quirks, and cultural moments that helped define a generation. That same spirit of fun and personality is what this contest is all about.

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.

Head up to one of Key West’s most iconic rooftops for a laid-back afternoon at the La Concha pool. Perched above Duval Street, this elevated oasis offers sweeping views of Old Town and the ocean beyond—an unexpected escape right in the heart of it all.

Join Just a Few Friends for a casual poolside hang with music, drinks, and easygoing energy as the weekend winds down. Whether you’re cooling off in the water, lounging in the sun, or catching a breeze with a cocktail in hand, it’s the perfect way to spend a Key West afternoon.

Relaxed, social, and just the right pace for a Monday—come take it all in from above the street.

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 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.

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.

Before everyone heads home, gather one last time at the legendary Chart Room for a relaxed farewell happy hour exclusively for Ultimate Friends.

This casual gathering is a chance to trade stories from the weekend, reconnect with new friends, raise a final toast, and start making plans to do it all again next year. Tucked inside the historic Pier House Resort, the Chart Room remains one of Key West’s most iconic watering holes—a place filled with decades of music history, island lore, and unforgettable moments.

Come by for a drink, a laugh, and one last hour together before the weekend drifts into memory.

Island Adventure Sandbar – Sunset Edition

Close out the weekend on the water with a laid-back backcountry escape that captures the natural side of Key West.

This 3.5-hour sunset tour takes you beyond the harbor to a remote sandbar, where the pace slows down and the surroundings take over. Swim in shallow turquoise water, relax on floating mats, try paddleboarding, or join a guided kayak tour through the mangroves.

As the evening unfolds, enjoy time to unwind with food, drinks, and open space before settling in for a Key West sunset on the return cruise. It’s easy, social, and just adventurous enough—designed to decompress and take in the beauty of the island at the right pace.

Watch Cayman & the Mango Men from the water aboard your own floating tiki hut.

This 2.5-hour Cruisin’ Tikis experience departs at 5:45 PM and makes its way into position just offshore from Sunset Pier, where you’ll take in the full concert from a relaxed, on-the-water vantage point. As the sun sets and the music begins, you’ll have a clear, uninterrupted experience of the show—paired with the movement of the harbor and a classic Key West evening.

Each tiki boat holds up to six guests and is BYOB, making it a fun, social way to enjoy the music with your own crew. Easy, unique, and unmistakably Key West.

Join hosts Jill and Sean for a relaxed sunset sail aboard the 75-foot luxury catamaran Argo Navis—one of the best ways to experience Key West from the water.

This all-inclusive evening is designed to be easy and social. Enjoy unlimited fine wines, craft beers, specialty cocktails, and non-alcoholic beverages, along with a steady flow of passed appetizers, all served by a top-tier crew while you settle in and unwind.

With spacious indoor and outdoor lounge areas, comfortable seating, and private onboard restrooms, the Argo Navis offers a smooth, comfortable ride as the sails go up and the evening begins to slow down.

For Jill and Sean, this isn’t just another sail—it’s a favorite tradition. As former crew members (with Sean still serving as a relief captain), they invite you to experience the water the way they’ve always loved it: simple, relaxed, and shared with good company.

Close out the weekend where it belongs—at Sunset Pier, with the sun dropping into the Gulf and the music carrying across the water.

Ease into the evening with a drink, grab dinner, and settle in as the crowd builds and the sky shifts into sunset. This is Key West at its best—uncomplicated, social, and set to a familiar soundtrack.

At 6:00 PM, Cayman & the Mango Men, a local Key West tribute band, perform a set of early classics drawn from Cayman’s own memories growing up on the island. Raised by pirates and smugglers, Cayman brings a taste of authenticity to these songs, having lived the lifestyle so many search for.

Backed by the Mango Men, the set leans into the early catalog with an easy, authentic feel—songs that land just right in this setting, at this time of day, with the breeze coming off the water.