6.5 hour excursion on a skipjack schooner for a full day of fun and sun on the water. Enjoy plenty of time snorkeling as well as kayaking around one of the mangrove islands and weather permitting, a stop at an island with a beach or a sandbar while taking in all the beauty of our Florida Keys Ecosystem.

Between activities, you'll enjoy a full lunch while you relax and take in some sailing. Beer, wine, water, sodas, and snacks are also provided - tin cup optional!

📍 Community Sailing Center | ⏳ 3 hours | 🎟 Includes certificate | 💙 Benefits Youth Sailing

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.

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.

Do you have the perfect pencil-thin mustache—or is yours more on the bushy side, Bubba? Just a Few Friends, The Chart Room at the Pier House, and Beards and Brews invite you to showcase your facial hair flair in our Second Annual Mustache Contest for a shot at epic bragging rights and fantastic prizes. This spirited event pays homage to the iconic song “Pencil Thin Mustache” and the unforgettable facial hair that often accompanied a certain beloved island troubadour. Whether your look is legendary, laughable, or lovingly fake, we've got a category for you.

🏆 Trophies will be awarded in: • Best Look-Alike • Best Pencil-Thin Mustache • Best Creative Mustache

🎖️ A People’s Choice Best of Show will be selected from the three winners. The grand prize? Two round-trip tickets on the Key West Express, a two-night stay at the Pier House, dinner for two at One Duval, a deluxe gift package from Beards & Brews, a limited-edition bottle of First Legal Agave Spirits—and the glory of holding the reigning title.

📍 Where: The legendary Chart Room Bar—where Key West’s favorite son once strummed his way into local lore

🕑 When: Registration from 2:30 to 3:00 PM | Contest begins at 3:00 PM

Expect free stick-on mustaches, photo ops, live trop rock tunes, poolside drinks, and Chart Room charm. Plus, the award-winning barbers from Beards & Brews will be onsite crafting artistic trims for anyone looking to level up their look.

Whether your ‘stache is natural or not, join us for a hilarious, hair-raising good time. Come for the fun—leave with a trophy.

A Bit About the ‘Stache

The pencil mustache—a thin line of facial hair just above the upper lip—first gained popularity in the 1930s and ’40s, worn by Hollywood icons like Clark Gable, David Niven, and Errol Flynn. Its sleek style was seen as sophisticated and suave. Jimmy Buffett gave this facial hair its own place in pop culture history with his 1974 hit “Pencil Thin Mustache.” The song is a nostalgic nod to post-war Americana, TV shows, and bygone icons, written from the perspective of a young boy who yearns for the grown-up world of mystery, coolness, and mustaches. Both tongue-in-cheek and deeply rooted in pop memory, it’s a song that celebrates the eccentric characters who helped shape our collective sense of style and swagger. And that’s exactly what this contest is all about.

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, present, and perfect way to toast the sunset.

As the sun sets over the ocean, Festival Badge holders are invited to an exclusive, intimate evening of music and storytelling at Sunset Pier: Sunset & Bubbles Songs and Stories with Will Kimbrough presented by Chandon Garden Spritzer. Gates open at 5:30 PM for badge holders only, with the performance beginning at 6:30 PM. Seating is limited, so arrive early to grab the perfect spot, order a cocktail, and settle in for a one-of-a-kind experience. A full bar and menu will be available throughout the show and Radio Trop Rock (https://radiotroprock.com/) will be broadcasting live.

Acclaimed singer, songwriter, and master guitarist Will Kimbrough takes the stage to share the songs and stories behind his music, including his work with Jimmy Buffett, Emmylou Harris, Todd Snider, and Rodney Crowell. A key collaborator on Buffett’s final album, Kimbrough co-wrote Bubbles Up—a song that has become an emotional anthem for fans worldwide. With his signature blend of soulful vocals, expert musicianship, and personal anecdotes, he'll take guests on a journey through the rhythms and tales of life on the road, island inspirations, and his deep connection to Buffett’s legacy.

With the ocean breeze, a front-row view of the sunset, and the sounds of world-class music filling the air, this promises to be an unforgettable night honoring the music, memories, and laid-back spirit of the Keys. Festival Badge required for entry.

Seating is first come, first served. 🌅🎶🍹

Argo Navis Dockside Lounge for the Will Kimbrough Concert: Step aboard the elegant Argo Navis, a luxury 65-foot catamaran, docked just steps from the Sunset Pier stage, for an exclusive VIP concert viewing experience. From 6 to 8:30 PM, enjoy open bar service, delicious passed appetizers, private restrooms, and premium lounge seating with come-and-go access throughout the show.

Whether you're sipping cocktails under the stars or catching the breeze between sets, this is your front-row escape for an unforgettable evening with Will Kimbrough. A celebrated singer-songwriter, guitarist, and longtime collaborator of Jimmy Buffett, Will brings lyrical depth, coastal soul, and authentic trop rock energy to every performance. This is the elevated way to experience live music—up close, uncrowded, and a fantastic way to bring the celebration with Just a Few Friends to a close.

See the concert on Sunset Pier from the comfort of your very own floating tiki hut! This BYOB experience is limited to just 6 friends on each tiki and offers the best views of the stage and the sunset.

Last Call, Long Story

Live at Surly Siren Saloon | Monday, Sept. 1 | After the Sunset Pier Concert

Join us for the final flicker of the Just a Few Friends weekend with an intimate, no-holds-barred set from Cayman Smith-Martin—where the stories get longer, the songs hit deeper, and nobody wants to say goodnight.

Fresh off Will Kimbrough’s Sunset Pier show, we’ll drift into the Surly Siren Saloon for one last toast, a few strums, and the kind of gritty, salt-stained soul Cayman brings best.

No cover. No shoes required.

Cocktails, cool air, and questionable decisions served nightly.

Because every great weekend deserves a closing chapter worth remembering.

“Aʟʟ ᴇᴠᴇɴᴛs ɴᴏᴛ ᴀꜰꜰɪʟɪᴀᴛᴇᴅ ᴡɪᴛʜ ᴏʀ ᴇɴᴅᴏʀsᴇᴅ ʙʏ Jɪᴍᴍʏ Bᴜꜰꜰᴇᴛᴛ’s Esᴛᴀᴛᴇ ᴏʀ Mᴀʀɢᴀʀɪᴛᴀᴠɪʟʟᴇ Eɴᴛᴇʀᴘʀɪsᴇs.”