Join fellow Just a Few Friends guests for an unforgettable on-the-water experience as you set out aboard a state-of-the-art Fury catamaran for a dolphin watch and backcountry snorkel adventure. Cruise into the turquoise waters of the Gulf of Mexico in search of Key West’s resident dolphins, observing them responsibly in their natural habitat alongside a Dolphin SMART–certified crew who share insight into the local population. Afterward, head into the shallow backcountry for a relaxed snorkel where you’ll encounter coral, sponges, and tropical fish in warm, clear waters—no experience needed, with all gear and instruction provided. Throughout the trip, enjoy complimentary beverages including beer, wine, sodas, and water as you connect with other “friends” and experience a quieter, natural side of Key West before or between festival moments.

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.

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).

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.

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 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, a Pirate Looks Back 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.

Jill and Sean, longtime market organizers and the team behind Just a Few Friends, invite you to spend a relaxed afternoon at the waterfront enjoying one of Key West’s favorite local traditions.

Set against the backdrop of the harbor, this open-air market brings together a vibrant mix of vendors offering fresh produce, local seafood, baked goods, tropical art, handmade crafts, boutique jewelry, and a diverse lineup of international food. It’s a true reflection of the island’s creative spirit and everyday culture.

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.

Ultimate Friends are invited to kick things off with a relaxed welcome gathering at the legendary Pier House Resort before the festival officially gets rolling. Held in the lobby area just outside the iconic Chart Room, this is your first chance to connect with fellow guests, meet the JAFF concierge team, and settle into island mode.

Pick up your swag, schedules, and event materials, take care of any last-minute questions or needs, and raise a toast to the days ahead with a Key West Legal Rum punch served in a special commemorative reusable bottle created just for Ultimate Friends.

Whether you’ve just arrived on the island or are already easing into the rhythm of the weekend, this is your home base to get oriented, get excited, and officially begin the celebration.

Who makes the best hamburger with cheese in a tropical place? You be the judge—right on the beach.

Join us for a lively, toes-in-the-sand showdown where some of Key West’s favorite restaurants and caterers go head-to-head, each serving up their take on the ultimate tropical cheeseburger. Sample your way through the competition, cast your vote, and help decide who takes the title.

Returning to defend their crown is Surly Siren—but this year they’ll face serious competition, including Margaritaville itself serving side by side, plus a lineup of contenders ready to bring their best. It’s anyone’s game.

Set against the backdrop of the ocean at sunset, this is more than a tasting—it’s a full-on beach party. Grab a drink, feel the breeze, and settle in as Jimmy Buffett tribute band Gypsies in the Palace takes the stage at 5:30 PM with a set of classic island favorites to keep the energy going all evening.

Gates open at 4:30 PM with bars and food available. Burger tasting and voting run from 5:00 PM to 7:00 PM. Votes must be turned in by 7:15 PM with winner announced at 7:45 PM

Tasting tickets are limited to just 300 and will sell out—this is one you don’t want to miss.

Presented by Just a Few Friends, Southernmost on the Beach Resort and Faustos Food Palace

Leave your worries behind and ease into the Just a Few Friends weekend with a sunset sail designed for connection, music, and that unmistakable Key West energy.

Step aboard a spacious, state-of-the-art Fury catamaran and join fellow “friends” for an unforgettable evening on the water—where the lines between strangers and friends tend to disappear somewhere between the harbor and the horizon. With live music setting the tone, this is where the weekend begins to take shape, surrounded by people who came for the same reasons you did.

Enjoy complimentary beverages throughout the sail—including margaritas, champagne, beer, wine, and non-alcoholic options—along with a selection of light appetizers as you cruise into open water. Take in wide-open views from the expansive deck as the sky shifts into full sunset color, the breeze picks up, and the music carries across the water.

Every Thursday at Andy’s Cabana—just across from Blue Heaven on Petronia Street—the stage comes alive with a rotating mix of local musicians, visiting artists, and whoever happens to be in town for “Open Mic / No Mic Night.”

Stop by, grab a drink, and settle in for a completely unscripted soundtrack—you might hear island classics, original songs, country, rock, or something entirely unexpected. It all depends on who shows up and what they feel like playing.

This laid-back gathering is an easy way to meet fellow music lovers and ease into the Key West rhythm—no set list, no expectations, just music in the moment. Got an instrument? Bring it along—you’re welcome to jump in and play, or even join the fun in Sunday’s Second Line Parade.

Once the Cheeseburger Beach Battle wraps, this is where the night continues.

Join us at the original Margaritaville Café—an iconic Key West landmark and a must-stop to kick off the weekend. Step inside and you're surrounded by decades of music, memorabilia, and moments that helped shape the lifestyle so many come here to celebrate. It's part hangout, part time capsule, and entirely Key West.

Grab a drink, find your people, and soak it all in—pose for a few photos, explore the memorabilia, and settle in for a special evening of live music featuring Nadirah Shakoor and her band.

As one of the most recognizable voices in the Coral Reefer Band for more than three decades, Nadirah has helped bring Jimmy Buffett's music to life on stages around the world. Joined by acclaimed singer-songwriter Claire Finley, expect an energetic, soulful performance filled with familiar favorites, outstanding musicianship, and the kind of musical moments that only happen in Key West.

No cover. Cash bar.

Come as you are and help us launch the weekend in the place where so many Key West stories began.