Ready to run, walk, stroll—or just make your way to margaritas?

Join us for the 3rd Annual Parrots & Margaritas 5K presented by Kaya Island Eats and take on Duval Street in full island style. Whether you’re chasing a personal best or just along for the ride, this is all about fun, friends, and a finish line worth celebrating.

Not feeling a full 5K? The Flip-Flop Mile kicks off after the main race—perfect for those who prefer a more relaxed pace (and maybe a drink in hand). Same vibe, same celebration… less mileage. Everyone finishes at Kaya Island Eats for one of the best post-race parties in Key West—complete with margaritas, tropical tunes, and a crowd that knows how to celebrate.

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.

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.

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.

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.

Set your course for adventure with this laid-back introduction to life under sail—hosted by the Key West Sailing Center, a nonprofit organization dedicated to making sailing accessible to the community and inspiring the next generation through youth programs, education, and time on the water.

Whether you're chasing new skills or just wondering what kept our favorite son coming back to the sea, this is your chance to find out. We’ll start on land with some easygoing instruction and practical rigging, then cast off for hands-on learning aboard a stable, beginner-friendly sailboat. You’ll get a taste of helm time, crew work, and the sheer joy of catching the wind. There’s even time to simply drift and take it all in—because every sailor deserves a moment like that.

Go behind the scenes at the award-winning Key West First Legal Rum Distillery with owner, founder, and chef Paul Menta. This exclusive VIP experience includes a guided tour of the production process, colorful stories of island history and distilling mischief, and complimentary tastings of handcrafted rum—including the limited-edition “Agave Tastes Like Vacation” bottle created just for this event.

This is experience is only available to Ultimate Friend Badge holders.

Ever seen a bar turned into a beach? Here’s your chance.

Step into the 801 Bourbon Sand Bar Party, where Duval Street meets a full-on tropical takeover. Sand underfoot, drinks in hand, and music in the air—this is Key West doing what it does best.

801 Bourbon Bar, a longtime island institution known for its anything-goes energy and welcoming vibe, transforms into a pop-up beach party right in the middle of Old Town. It’s part spectacle, part hangout, and all about letting loose.

Tiki Man Radio broadcasts live throughout the day with B-Man and Mi-Shell, bringing a steady flow of island music, interviews, and familiar voices that keep the party moving..

Step into an intimate afternoon of storytelling, laughter, inspiration, and island culture as Just a Few Friends presents A Few Stories with Friends — a curated showcase featuring authors, historians, photographers, and storytellers whose work has been inspired by Jimmy Buffett, Key West, and the spirit of life lived just a little differently.

This moderated multi-author experience brings together a fascinating mix of voices from across the Parrothead world — from longtime Key West historians and music writers to novelists, photographers, and fans whose lives were forever shaped by the music, community, and mythology surrounding the island lifestyle.

Rather than a traditional lecture, the event is designed as a lively, fast-paced storytelling experience where each featured guest will share the inspiration behind their work, personal connections to Key West and Buffett culture, and the stories that happened between the songs.

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).

Go behind the scenes at the award-winning Key West First Legal Rum Distillery with owner, founder, and chef Paul Menta. This exclusive VIP experience includes a guided tour of the production process, colorful stories of island history and distilling mischief, and complimentary tastings of handcrafted rum—including the limited-edition “Agave Tastes Like Vacation” bottle created just for this event.

This is experience is only available to Ultimate Friend Badge holders.

Join us for a relaxed, mid-day escape on the water—created exclusively for Best Friend VIP package guests.

This easygoing harbor cruise is just enough time to get out, unwind, and take in Key West from a different perspective without taking over your day. It’s the perfect reset before heading back into the energy of the afternoon, with plenty of time to make the Margarita Stroll and everything else Saturday has to offer.

Singer-songwriter Cliff Cody joins as special guest, bringing a laid-back live set to the experience. As one of the last artists to record at Jimmy Buffett’s Shrimp Boat Sound studio, his music adds a meaningful connection to the place and the story behind it all.

Take a short ride over to Stock Island and settle in for a true locals’ afternoon at one of the Lower Keys’ most beloved hidden gems. Tucked away in Safe Harbor Marina on Stock Island, Hogfish Bar & Grill isn’t just a locals’ spot—it’s THE locals’ spot. No frills, no nonsense—just strong pours, killer waterfront views, and that old-school Florida Keys charm you won’t find on Duval.

 Saturday anytime between 11 am and 1 pm we invite you to join us for lunch, great music and fun photo ops!

You’ll also have the chance to meet and get pictures with some of the contestants from Friday night’s Bubba Look-Alike Contest.

Hosted by the Key West Parrot Head Club

Join the Key West Parrot Head Club for a meaningful Paddle Out—a floating, on-the-water tribute honoring the life, music, and legacy that brings us all together.

Rooted in surf culture, a paddle out is a simple but powerful ceremony. Participants head out beyond the shoreline on boards, kayaks, or anything that floats, gathering together on the water to form a circle. There, the group shares a moment—through silence, stories, reflection, or song—before releasing flowers or ocean-friendly offerings into the water.

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, 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.

Spend your Saturday afternoon poolside at Margaritaville Beach House—where the pace is easy, the drinks are cold, and the vibe is exactly what you want it to be.

Join in for a laid-back afternoon with music, sunshine, and plenty of space to kick back or cool off. Whether you’re floating in the pool, lounging with a drink in hand, or catching up with friends, this is an easy reset in the middle of a full weekend.

Located just across from Smathers Beach, the resort offers a more relaxed, open-air setting—perfect for stepping away from the crowds while still staying in the flow of the festival.

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.

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.

In Key West, the margarita is more than just a cocktail—it’s a symbol of island life, celebrated in songs, sunsets, and good times with friends. It’s only fitting that our festival honors this iconic drink with a lively stroll through some of the island’s best bars, raising a glass to the music, magic, and tropical spirit that brings Just a Few Friends together.

Who has the best margaritas in Key West? Find out on one of two simultaneous Margarita Bar Strolls with Just a Few Friends!Choose your adventure—stroll iconic Duval Street or sip your way around the Historic Seaport. Both routes offer at least eight beloved bars ready to serve you their signature margarita, a cold brew or a delicious mocktail, if you prefer.

Each stroll is limited to 200 participants, so grab your fellow fans and register early! This always sells out.

🎟️ $48 includes an official event t-shirt. Choose your shirt size through August 1.

In Key West, the margarita is more than just a cocktail—it’s a symbol of island life, celebrated in songs, sunsets, and good times with friends. It’s only fitting that our festival honors this iconic drink with a lively stroll through some of the island’s best bars, raising a glass to the music, magic, and tropical spirit that brings Just a Few Friends together.

Who has the best margaritas in Key West? Find out on one of two simultaneous Margarita Bar Strolls with Just a Few Friends!Choose your adventure—stroll iconic Duval Street or sip your way around the Historic Seaport. Both routes offer at least eight beloved bars ready to serve you their signature margarita, a cold brew or a delicious mocktail, if you prefer.

Each stroll is limited to 200 participants, so grab your fellow fans and register early! This always sells out.

🎟️ $48 includes an official event t-shirt. Choose your shirt size through August 1.

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.

How well do you really know Key West’s favorite son?

Join us for a fun, laid-back round of trivia covering the songs, stories, lifestyle, and legends that helped shape the music and the island. From deep cuts to iconic moments, it’s all fair game.

Bring your own team or join up with a few new friends—it’s all about good questions, great company, and a few laughs along the way. With the bar open and the vibe easy, it’s the perfect way to keep the afternoon going.

🏆 Fun prizes awarded to the top teams

Step aboard the 75-foot luxury catamaran Argo Navis for a relaxed, all-inclusive sunset sail with fellow Just a Few Friends guests—an elevated way to wind into the evening.

As the sails go up and the breeze settles in, enjoy unlimited fine wines, craft beers, specialty cocktails, and non-alcoholic beverages, along with a selection of passed appetizers served by a top-tier crew. With spacious indoor and outdoor lounge areas, comfortable seating, and private onboard restrooms, it’s an easy, social way to experience the water in style.

This sail is perfectly timed to flow into the evening’s dockside performance by the Wheeland Brothers—known for their sun-soaked blend of surf, reggae, and country-inspired sound. Their music is built for ocean air, golden hour, and easygoing nights, making this the ideal lead-in to the show.

The trip departs from and returns to the docks at Sunset Pier, bringing you back at approximately 7:50 PM—placing you exactly where you need to be as the music begins at 8:00 PM.

Guests may choose to disembark upon return—or upgrade their experience by adding access to the Wheeland Brothers Dockside Party aboard the Argo Navis at checkout for an additional $65. This upgrade includes an unlimited open bar with attentive waitstaff, light snacks, and relaxed seating as you enjoy the concert dockside from the bow of the vessel—no crowds, no lines, and a clear view of the stage.

During the opening act, the vessel will be sailing, offering guests on the combo experience a different perspective before returning dockside for the main performance.

Take the party offshore aboard your own floating tiki hut and experience the Sunset Pier show from the water.

This two and half-hour Cruisin’ Tikis trip departs at 6:15 PM and cruises through the Key West harbor before making its way into position off Sunset Pier. Along the way, you’ll catch portions of both Mike Stack & Friends and the Wheeland Brothers as the music carries across the water—blended with the sounds of the harbor, the movement of the boat, and a classic Key West sunset.

This isn’t about a front-row view of the stage—it’s about the experience. From golden hour to nightfall, you’re part of the full transition as the evening unfolds, with the concert as your backdrop.

Each tiki boat holds up to six guests and is BYOB, making it a fun, social way to enjoy the night with your own crew. Relax, drift, turn up your own music between sets, and take it all in from a perspective most people don’t get to see.

A uniquely Key West way to be part of the show—without ever stepping on the pier.

Limited availability.

Set sail into the evening aboard a historic Key West schooner for one of the most refined—and relaxed—experiences on the water.

Danger’s Wind & Wine Sunset Sail is consistently ranked among the best in North America, and once you’re aboard, it’s easy to see why. Under full sail and open sky, you’ll drift through the backcountry enjoying a curated selection of fine wines from around the world, complemented by upscale beers and a generous spread of hors d’oeuvres designed to match the setting.

This isn’t a party cruise—it’s something more intentional. A quieter, more elevated way to take in the sunset, the breeze, and the company around you.

Adding to the experience, special guest Caleb Hogan—star of A Pirate Looks Back—joins the sail with a live, stripped-down performance. Known for bringing Jimmy’s early Key West years to life through music and storytelling, Caleb adds a personal, intimate layer that fits perfectly with the setting.

As the light fades and the sails fill, this is the kind of evening that doesn’t need much else—just good wine, good music, and the feeling of being exactly where you’re supposed to be.

There’s no better place in Key West to watch the sun go down than Sunset Pier—and on Saturday, it comes with a soundtrack.

At Just a Few Friends, honoring Jimmy’s legacy also means embracing the next wave of artists who carry that same spirit of independence and storytelling—even when it doesn’t fit neatly into a single genre. Mike Stack represents that evolution. His breakout track “I’m From Key West” has become a local anthem, capturing the pride, personality, and cultural mix of the island in a way that resonates with both longtime locals and new fans.

That energy takes the stage at 6:30 PM as Mike Stack & Friends kick off the night with a fresh, high-energy set that reflects where the Key West sound is headed—not just where it’s been. Blending hip hop, island vibes, and country influences, Mike is joined by Shareese, Marjory Lee, Pierce August, and D-Lew for a collaborative set full of genre-crossing moments, unexpected mashups, and individual spotlights that build momentum for the night ahead.

As the sun drops, the Wheeland Brothers take the stage, bringing their signature blend of surf rock, reggae, and acoustic storytelling to the waterfront. Part of a new wave shaping the next chapter of the genre, they carry forward that familiar coastal spirit while making it distinctly their own.

You might catch a familiar nod or a Buffett cover woven in, but the heart of the set is their original music—songs built for sunshine, salt air, and living life a little more barefoot. Known for their high-energy performances and natural connection with the crowd, they deliver a sound that feels right at home in Key West while pushing the scene forward.

Different sounds, same setting—sunset, good company, and a night that builds from the first note to a full-on dance floor.

This set is an invitation to lean into something different, discover new sounds, and enjoy the kind of laid-back, anything-goes energy that defines both Key West and this weekend.

You're invited to take in the Wheeland Brothers from one of the most unique vantage points in Key West—aboard the Argo Navis, docked at Sunset Pier.

A limited number of guests will experience the show from the bow of this 75-foot luxury catamaran, with relaxed seating, private onboard restrooms, light snacks, and an unlimited open bar served by attentive crew. It’s a comfortable, elevated way to enjoy the music—right on the water, just steps from the stage. No crowds, no one standing in front of you, no lines, no waiting for drinks.

You can choose your experience. Join us dockside for the full concert atmosphere at Sunset Pier, or upgrade to the Sunset Sail + Dockside Party combo and arrive by water just before the music begins.

The sunset sail returns to the dock at 7:50 PM, just in time for additional dockside guests to board the Argo Navis before the 8:00 PM Wheeland Brothers start time—bringing everyone together as the show gets underway. During the opening act, the vessel will be sailing, offering guests on the combo experience a different perspective before returning dockside.

Settle in for an easygoing evening under the stars at The Pint & Blast Beer Company, where the exterior wall becomes the screen for the Friends of Bubba Video Lounge—a casual, come-and-go experience with music, memories, and nostalgic moments playing all night long.

Enjoy a curated mix of officially released clips, music videos, live performances, and archival footage rolling continuously throughout the evening, projected large for a laid-back outdoor viewing experience that feels right at home in Key West.

Keep It Going… Back Yard EmPOURium After Party

After the Wheeland Brothers wrap at Sunset Pier, this is where the night picks back up.

Back Yard EmPOURium offers an easy, open-air setting right on Duval—part backyard hangout, part late-night gathering spot. It’s the kind of place you can roll into with your group, grab a drink, and keep the momentum going without missing a beat.

Live music will be announced soon, but expect a strong set to carry things through the evening. Whether you’re coming straight from the Pier or making your way through town, it’s a natural next stop as Saturday night continues to unfold.

No cover. Cash bar.