Saturday, September 5th
Painting Paradise: A Guided Plein Air Experience
Session Two: Louis Back Yard
Louis Back Yard
9 AM
varies
Painting Paradise: A Guided Plein Air Experience
Slow down, step outside, and see Key West through a different lens.
As part of Just a Few Friends, we’re offering two intimate guided plein air sessions at iconic island locations with deep creative roots. Whether you’re an experienced artist or simply someone who enjoys sketching and watercolor, this relaxed outdoor experience invites you to capture the architecture, light, and atmosphere that define Key West.
Each two-hour session includes a brief introduction to the site, light guidance from a local instructor on composition and capturing the island’s distinctive light, and plenty of time to create your own interpretation. Participants may work in watercolor, colored pencil, or drawing mediums. All artwork will be completed on mounted paper suitable for optional display during Party in the Park.
Session Two: Louie’s Backyard
Saturday, August 30, 2025
9:00 AM – 11:00 AM
Capture one of Key West’s most photographed homes, perched above the Atlantic with its signature wraparound balconies and sweeping ocean views. This session emphasizes atmosphere, movement, and coastal light.
Guests may register for one session or both. Space is limited to 24 guests to maintain a relaxed and personal experience. Participants are welcome to bring their own materials, or reserve a festival-prepared paper and mounting kit. Optional watercolor kits are also available for traveling artists.
Participants are invited to leave their finished works with us for inclusion in the pop-up “Painting Paradise” exhibit at Party in the Park. Following the exhibit, artwork may be collected at the end of the weekend or shipped directly to you.
Private Distillery Tour with Paul Menta
Key West Legal Rum
10 AM
Invitation Only
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.
Coconut Telegraph Trolley Tour
Pier House
10 AM
$80.00
Climb aboard the Just a Few Friends Trolley Tour for an unforgettable narrated journey through the Key West landmarks that shaped his life and music. This comprehensive island tour goes beyond the walking tour, covering more ground and deeper stories as you pass by iconic sites tied to Buffett’s time in the Conch Republic.
Roll past the bars, streets, and hideaways that inspired his legendary songs, with a special stop at Dog Beach and Louie’s Backyard, where Jimmy once lived, and a visit to his former home in New Town. Along the way, your guide will share insider stories, historic moments, and the lasting influence of Buffett’s island life. Whether you're a longtime fan or just discovering his legacy, this tour offers a one-of-a-kind glimpse into the Key West that Jimmy called home.
Just a Few Friends Walking Tour
Shrimp Boat Sound
10 AM
$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.
Sails Up: Intro to Sailing Experience
Key West Sailing Center
10 AM
$60.00
Set your course for adventure with this laid-back introduction to life under sail. 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. We’ll even leave room for a little time to just play—because every sailor deserves to drift now and then. Each participant receives a completion certificate, and best of all, proceeds support the Sailing Center’s youth programs and camps, helping the next generation of island dreamers discover the magic of the sea. No experience needed—just bring your flip-flops and a little sense of wonder.
Ultimate Friend's Private Distillery Tour with Paul Menta
Key West Legal Rum
11 AM
Invitation Only
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.
Back to the Island Beach Party
Bourbon Street Pub
11 AM
Free
Have you ever seen a bar filled with sand? Welcome to the 801 Bourbon Sand Bar Party—where Key West’s legendary party spirit meets an epic tropical takeover!
801 Bourbon Bar, a Duval Street icon known for its colorful history, high-energy atmosphere, and everyone’s-welcome attitude, transforms into a pop-up beach bash right in the heart of Old Town.
Tiki Man Radio will be broadcasting live from the scene with hosts B-Man and Mi-Shell, adding their signature island sounds, interviews, and tropical flair to the party.
Part of the Margarita Bar Stroll, this stop offers great drink specials, spontaneous sing-alongs, and plenty of opportunities to dance (or just dig your toes in the sand).
It’s a come-as-you-are, bring-your-friends, and live-your-best-island-life kind of vibe—all day long!
A Pirate Looks Back," - the Key West Jimmy Buffett tribute show
Comedy Key West
12:30 PM
$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.
Chart Room Daily Hangout Headquarters
Pier House
1 PM
Free
Wind down or gear up with daily happy hour at the legendary Chart Room Bar—one of the most storied watering holes in Key West. Join your friends (and meet new ones) for drink specials exclusively for JAFF badge holders, plus free popcorn, peanuts, and all the laid-back charm you’d expect from this historic hideaway. Enjoy trop rock music each evening from the very spot where a young singer-songwriter once sat with a guitar and a dream—long before he became a household name. The Chart Room isn't just a bar—it’s part of the story. And happy hour here is your front-row seat to the past and present.
Tales from the Chartroom
Pier House
1:15 PM
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.
Milagro Margarita Historic Seaport Bar Stroll
The Marker Resort
2 PM
$45.00
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—or a cold brew, if you prefer.
Each stroll is limited to 200 participants, so grab your fellow fans and register early!
🌴 Lost Shaker of Salt Scavenger Hunt!We’ve misplaced our shaker of salt—and you can help us find it!Oversized salt shakers are hidden at various participating bars.Snap selfies with at least five of them, post your photos on Facebook or Instagram, tagging "Just a Few Friends, Key West" and the bar you're at, and you’ll be entered to win:
🎟️ Round-trip tickets for 2 on the Key West Express
🍹 A limited-edition signed bottle of Key West’s "Taste Like Vacation" Agave Spirits
🎁 A swag bag from The Green House
Winners will be drawn and announced Sunday morning—good luck!
🍹 How it Works:
Check in at La Concha (Duval stroll) or The Marker Resort (Seaport stroll) between 11:00 AM and 2:00 PM to grab your event t-shirt and tasting guide.
Start at any participating bar on your map at 2:00 PM.
At each stop, enjoy one 4 oz margarita or beer and get your tasting guide marked. Pace yourself, it’s not a race so enjoy bar specials and grab a bite to eat along the way!
Use the QR code on your guide to rate your favorite margarita and help crown the 2025 Margarita Champion.
Milagro Margarita Duval Street Bar Stroll
La Concha
2 PM
$45.00
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—or a cold brew, if you prefer.
Each stroll is limited to 200 participants, so grab your fellow fans and register early!
🌴 Lost Shaker of Salt Scavenger Hunt!We’ve misplaced our shaker of salt—and you can help us find it!Oversized salt shakers are hidden at various participating bars.Snap selfies with at least five of them, post your photos on Facebook or Instagram, tagging "Just a Few Friends, Key West" and the bar you're at, and you’ll be entered to win:
🎟️ Round-trip tickets for 2 on the Key West Express
🍹 A limited-edition signed bottle of Key West’s "Taste Like Vacation" Agave Spirits
🎁 A swag bag from The Green House
Winners will be drawn and announced Sunday morning—good luck!
🍹 How it Works:
Check in at La Concha (Duval stroll) or The Marker Resort (Seaport stroll) between 11:00 AM and 2:00 PM to grab your event t-shirt and tasting guide.
Start at any participating bar on your map at 2:00 PM.
At each stop, enjoy one 4 oz margarita or beer and get your tasting guide marked. Pace yourself, it’s not a race so enjoy bar specials and grab a bite to eat along the way!
Use the QR code on your guide to rate your favorite margarita and help crown the 2025 Margarita Champion.
Early Access: Table Seating (JFF VIPs)
Big Stage
5 PM
VIP
Early Access: Table Seating (JFF VIPs) — JFF VIP guests get first access to Sunset Pier to claim the best tables, settle in with a cocktail, and enjoy dinner while the sun begins to dip over the Gulf. It’s the perfect way to ease into the evening before the crowd arrives, with prime positioning in front of the Big Stage for the night’s free concert and one of Key West’s legendary sunsets.
Early Access: Entry (JFF Badge Holders)
Big Stage
5:30 PM
Free
Early Access: Entry (JFF Badge Holders) — Event Badge holders receive early entry to Sunset Pier before general admission, giving them extra time to grab a drink, order dinner, and secure a great viewing spot near the Big Stage as the sunset sets the stage for the evening’s live music.
Doors Open (GA)
Big Stage
6 PM
Free
Doors Open (GA) — The gates open to everyone for this free waterfront concert at Sunset Pier. Come early, grab a drink or dinner from the bar and restaurant, and find your spot as the crowd gathers for an unforgettable night of music overlooking the Gulf of Mexico.
Cruisin' Tiki Sunset & Music Cruise
Cruisin' Tikis @ Mac's Place
6:30 PM
$79.95
Cruisin’ Tiki Sunset & Music Cruise — See the Wheeland Brothers concert from the comfort of your very own floating tiki hut. Known for their upbeat blend of California surf rock, acoustic grooves, and feel-good beach anthems, the Wheeland Brothers deliver the perfect soundtrack for a sunset on the water. This two-hour Cruisin’ Tikis experience lets you drift just offshore from Sunset Pier while enjoying the music, the sunset, and the Key West harbor. Each tiki boat holds up to six friends and is BYOB, making it a fun and unique way to experience the show and the island vibe from the water. Limited availability.
Latitude Adjustment Sunset Sail
The Dock @ Sunset Pier
6:30 PM
$111.00
Join hosts Jill and Sean on Saturday for a relaxing sunset sail aboard the beautiful 75-foot luxury catamaran SV Argo Navis, alongside fellow guests of the Just a Few Friends celebration.
This all-inclusive sailing experience features unlimited fine wines, craft beers, specialty cocktails, and non-alcoholic beverages, paired with delicious passed appetizers—all served by a top-tier crew while you sit back and unwind.
With ample space to move about, indoor and outdoor lounge areas, and hotel-style restrooms, this stable and stylish yacht offers an exceptionally comfortable way to enjoy the open water.
The sails are raised each evening, so guests experience the true magic of sailing—from the gentle motion across the sea to the soundtrack of wind and waves.
As former crew members (with Sean still serving as a relief captain), Jill and Sean invite you to share in one of their favorite ways to celebrate the Key West lifestyle.
Changes in Latitudes: Sunset Pier Concert featuring the Wheeland Brothers
Sunset Pier
8 PM
Free
Wheeland Brothers – Free Show (Big Stage) — California surf-rock favorites the Wheeland Brothers bring their signature blend of laid-back beach vibes, acoustic grooves, and feel-good anthems to the Big Stage at Sunset Pier. Known for their high-energy performances and infectious coastal sound, the band has built a loyal following with songs that celebrate sunshine, salt air, and living life a little more barefoot. As the sun sets over Key West, they’ll deliver a soundtrack made for summer nights by the water.
Outdoor Movie
Southernmost Pint Brewpub
8 PM
Free
Settle in for an evening under the stars as we screen Parrot Heads – The Essential Jimmy Buffett Documentary. This fan-favorite film dives into the incredible community inspired by Jimmy Buffett’s music and laid-back lifestyle, exploring how one man’s songs built a worldwide family of devoted, flip-flop-wearing, island-loving fans.
Learn the story behind the phenomenon as told through rare interviews, concert footage, and the voices of Parrot Heads themselves.
The Pint and Blast Beer Company will be pouring small-batch craft brews and offering rotating gluten-free menu favorites all night. Beer and wine are available for purchase, and beach chairs are provided for a cozy, casual Key West evening under the stars.
Come toast to the music, the memories, and the community that keeps the island spirit alive.