Start your Sunday the easy way with a relaxed brunch at Margaritaville Beach House.

Settle in with live acoustic music and enjoy a special brunch menu featuring breakfast favorites, island-inspired dishes, cocktails, coffee, and laid-back resort vibes. Whether you’re fueling up for the day ahead or easing into a slow Key West morning, it’s the perfect place to gather with friends and enjoy the rhythm of the island.

Order what you’d like directly from the brunch menu and stay as long as you like—no reservations necessary.

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.

Join us for a one-of-a-kind brunch sail aboard the luxurious 75' Argo Navis, with Will Kimbrough and his wife Jessica along for the sail. As part of the Just a Few Friends Key West – Favorite Son Celebration, this exclusive two-hour experience blends breathtaking ocean views, delicious brunch, and refreshing bubbles—all with the unmatched service and comfort of Key West’s premier sailing yacht.

⛵ The Sail This isn’t just brunch dockside—it’s a true sailing experience. During your two-hour harbor cruise, the crew will raise the sails, cut the engines, and let the wind take over so you can experience Key West on the water the way it was meant to be enjoyed. Relax with panoramic views, warm ocean breezes, and the peaceful rhythm of sailing aboard one of the island’s most beautiful vessels.

🥂 Bubbles Enjoy unlimited mimosas and bubbly sangria, along with premium wines, Florida craft beers, Red Buoy Coffee, and signature Bloody Marys.

🍽 Brunch Indulge in a curated selection of passed dishes bringing the flavors of Key West right to your plate. Whether you're a local or visiting, this intimate sailing experience is the perfect way to sip, savor, and soak in the beauty of paradise with friends.

With limited capacity, personalized service, premium food and beverages, time on the water aboard a luxury sailing yacht, and the chance to spend the morning alongside Will and Jessica Kimbrough, this is designed to be one of the most memorable experiences of the weekend.

Spots are limited—reserve yours now and make this unforgettable brunch sail part of your Key West celebration before enjoying Will’s free performance later that evening at Party in the Park. ⛵🥂🌞

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.

Take a break from the bustle and soak up the sun at one of Key West’s most beautiful poolsides. The Marker Resort invites Just a Few Friends guests to kick back and cool off with live music, refreshing drinks, and good vibes across multiple pools.

A fun DJ will be spinning a mix of trop rock favorites and island classics—along with your requests—keeping the energy just right whether you’re lounging in the shade, floating in the water, or dancing poolside.

There’s no charge to attend, and the onsite full bar and snack bar will be open and ready to serve. It’s the perfect way to unwind and recharge before the Second Line Parade steps off.

Bring your badge, your beach towel, and your best island state of mind—this is what Sunday in paradise looks like.

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.

Take a break from the bustle and soak up the sun at one of Key West’s most beautiful poolsides. The Marker Resort invites Just a Few Friends guests to kick back and cool off with live music, refreshing drinks, and good vibes across multiple pools.

A fun DJ will be spinning a mix of trop rock favorites and island classics—along with your requests—keeping the energy just right whether you’re lounging in the shade, floating in the water, or dancing poolside.

There’s no charge to attend, and the onsite full bar and snack bar will be open and ready to serve. It’s the perfect way to unwind and recharge before the Second Line Parade steps off.

Bring your badge, your beach towel, and your best island state of mind—this is what Sunday in paradise looks like.

Settle in for an intimate, up-close performance with Roger Bartlett, original lead guitarist for Jimmy Buffett and a key part of the early sound that helped shape the music so many come here to celebrate. His playing is woven into the roots of it all, and this setting offers a rare chance to hear it the way it was meant to be experienced—personal, relaxed, and right in front of you.

 Joining Roger is accomplished concert violinist Emily Randle, a retired US Army sergeant major who is a lively addition to any stage.

Held inside the Key West EmPOURium Listening Room, this is a true listening experience—small, focused, and designed for those who want to connect more deeply with the music and the stories behind it. This ticketed event is co-hosted by the Key West Parrot Heads

This intimate performance is reserved exclusively for Best Friend VIPs—an up-close moment in one of the most iconic rooms in Key West. Capacity is limited to just 120 guests, creating a rare, small-room experience in the heart of it all.

Nadirah Shakoor, longtime vocalist with Jimmy Buffett’s Coral Reefer Band, brings a powerful, soulful presence that has helped define the sound of the music so many come here to celebrate. Her connection to the songs, the stories, and the community makes this a natural fit for Margaritaville, where it all comes full circle.

Set inside the original restaurant on Duval Street, this is a chance to experience the music in a more personal setting—close in, relaxed, and shared among a select group.

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.

Before stepping into the energy of the Second Line Memorial Parade, Ultimate Friends are invited to gather at Emerald’s International for a relaxed pre-parade reception in the heart of Old Town.

Cool off, grab a snack or refreshing mocktail, reconnect with friends, and settle in before the streets fill and the celebration begins. This casual gathering space offers a comfortable place to recharge and get parade-ready before making your way to the lineup.

UF will also be able to pick up commemorative placards to carry at the front of the parade procession.

Celebrate the life, music, and spirit of Key West’s favorite son with a joyful, tropical tribute filled with music, creativity, and community 🌴🎶 Led by Will Kimbrough & Howard Livingston—along with a few surprise friends—this lively procession brings the island together in one unforgettable moment.

The Second Line steps off promptly at 5:00 PM from the lower 100 block of Duval Street, winding five blocks down Duval, turning onto Southard Street, and continuing to Truman Waterfront Park for a casual waterfront celebration. Expect live music, group singalongs, and plenty of island-style fun along the way.

After the Second Line March winds its joyful way through town, the celebration continues at Party in the Park. Settle in on the Truman Waterfront lawn for an easygoing evening of live music, local flavor, and island energy as the festival comes together to celebrate the spirit of Key West and the songs that were born here.

The evening features performances by Howard Livingston and the Mile Marker 24 Band, Will Kimbrough, and Mac McAnally—three artists whose music and songwriting helped shape the sound and storytelling of the Gulf Coast and the Florida Keys. The night unfolds in true island fashion with a relaxed, come-and-go atmosphere on the waterfront lawn, perfect for kicking back and letting the music carry you through a beautiful Key West evening.

Howard Livingston and the Mile Marker 24 Band are the Florida Keys’ beloved trop rock troubadours, known for breezy island storytelling and songs that perfectly capture life in the Keys. Will Kimbrough, a celebrated songwriter, producer, and guitarist who collaborated closely with Jimmy Buffett in recent years, brings soulful musicianship and heartfelt storytelling to the stage. Mac McAnally—Grammy-winning songwriter, longtime Coral Reefer Band member, and one of Buffett’s closest musical collaborators—adds the unmistakable voice and musicianship behind many of the songs that defined the coastal sound of the region.

Beyond the music, explore the Key West Artisan Market Island Time Market & Food Court, featuring a curated collection of local artists, makers, and chefs. Browse tropical art, handmade jewelry, island-inspired gifts, boutique fashion, and delicious bites from food trucks and local vendors. You’ll also find full bars, specialty drink stations, and plenty of space to spread out on the lawn as the evening unfolds against the backdrop of a spectacular Key West sunset over the water.

Grab a cold drink - may we suggest a Milagro Margarita - sample delicious eats, shop a little, and find your spot on the lawn to soak up the tropical sounds. Whether you're dancing, relaxing, or simply taking it all in, Party in the Park is the signature gathering of the weekend—best shared with just a few friends.

As the energy builds at Party in the Park, take a stroll through the Key West Artisan Market pop-up.

Discover a vibrant mix of local artists, makers, and vendors offering everything from tropical art and handmade jewelry to island-inspired gifts and one-of-a-kind finds.

Grab a bite from the food trucks, sip something cold from the festival bars, and take it all in between sets. Whether you’re browsing, shopping, or just soaking up the waterfront atmosphere, the Artisan Market adds another layer to the biggest party of the weekend.