

Thursday, August 28
Just a Few Friends Walking Tour
9:30 AM
Shrimp Boat Sound
$45.00
Take a 90-minute guided walking tour through some of the most celebrated haunts in Key West, frequented by our favorite son over his expansive history here.
You'll visit the outside of his beloved music studio—where you’re welcome to leave a memento or sticker—and hear colorful stories about his pirate life in the Keys.
This laid-back stroll covers iconic sights, little-known secrets, and special moments tied to the music and spirit that shaped an island legend.
Cooking Show: Grits n Grunts
11 AM
Key West Cooking Show
$65.00
Step into the Key West Cooking Show for a lively culinary demonstration celebrating a true island classic. Learn the story and technique behind fresh grunt fish served over creamy grits while enjoying local food lore, chef tips, and a tasting of this beloved Keys dish.
A Pirate Looks Back, the Key West Jimmy Buffett tribute show
12:30 PM
Comedy Key West
$56.88
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.
Truman Waterfront Farmers Market`
1 PM
Truman Waterfront Park
Free
Jill and Sean, owners of the Farmers Market and event organizers for the Festival, invite guests down for a relaxed afternoon of fresh air, local flavors, and waterfront shopping in a beautiful seaside setting.
Browse a vibrant mix of vendors featuring fresh produce, seafood, baked goods, tropical art, handmade crafts, boutique jewelry, and international food offerings. Cool off with fresh juices, smoothies, and other refreshing beverages while you explore the colorful stalls and savor the island breeze.
It's also the perfect place for a casual picnic—grab a bite from the vendors and settle in at one of the extra chairs we'll have set up just for Just a Few Friends guests.
Tales from the Chartroom
2:15 PM
Pier House
Free
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 original creator of the Coconut Telegraph and a longtime member of the Margaritaville family—each 30-minute session features a different special guest sharing firsthand stories from the island scene that inspired the songs and the lifestyle.
Through a relaxed, guided conversation, Carol draws out inside insights and colorful memories of Key West adventures with friends, musicians, and characters who were there when it all happened. 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.
Sessions will also stream live on the Just a Few Friends Facebook page for fans following along from afar.
Cheese Burger Beach Battle and Tribute Concert
5 PM
Southernmost on the Beach
$25/$15
Who makes the best hamburger with cheese in a tropical place? You be the judge at our lively beachside competition!
Sample tropical cheeseburgers from at least eight of Key West’s favorite restaurants and caterers while you enjoy live island tunes and soak up the beach vibes.
The event kicks off at 5 PM with bars and food available. Burger tasting and voting run from 5 PM to 7 PM, and the Jimmy Buffett tribute band will take the stage at 5:30 PM for a lively set of classic hits, creating the perfect beach party soundtrack.
Tasting tickets are limited to 300 and are expected to sell out quickly!
“Open Mic / No Mic Night” at Andy's Cabana
7 PM
Andy's Cabana
Free
Every Thursday at Andy’s Cabana—just across from Blue Heaven on Petronia Street—the stage lights up with a rotating mix of local musicians and traveling troubadours for “Open Mic / No Mic Night.”
Stop by, grab a drink, and enjoy the spontaneous soundtrack of island life—you never know who might show up or step up to play!
This laid-back gathering is the perfect unofficial pre-party for Just a Few Friends, offering the ideal chance to meet fellow music lovers before the weekend gets rolling.
Got an instrument? Bring it along—you’re welcome to play a tune here or even join the fun in Sunday’s Second Line Parade.
📸 Photo credit: Bill Klipp