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.

Set sail in style aboard the luxurious 75' Argo Navis for a one-of-a-kind brunch experience as part of the Just a Few Friends Key West - Favorite Son Celebration! This exclusive two-hour sail offers the perfect blend of breathtaking ocean views, delicious brunch, and refreshing bubbles—all with the unmatched service and comfort of Key West’s premier sailing yacht.

🥂 Bubbles: Enjoy a Mimosa Bar & Bubbly Sangria, along with premium wines, Florida craft beers, Red Buoy Coffee, and signature Bloody Marys to toast to the good life.

🍽 Brunch: Indulge in a curated selection of local favorite 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.

Spots are limited—reserve yours now and make this unforgettable brunch sail part of your Key West celebration! ⛵🥂🌞

Join our friends at Shots and Giggles and the Key West Chamber of Commerce as they fire up the grills for the 6th Annual BBQ Rib Battle! Watch local BBQ masters go head-to-head in a sizzling cookoff, competing for cash prizes and bragging rights.

Ann Street transforms into a block-party-style showdown where you can sample mouthwatering ribs, enjoy delicious sides, sip drinks, groove to live music, and join the fun with a 50/50 raffle. Bring your appetite and your cheering voice—this is backyard BBQ, Key West style.

Tickets will be available cash only at the gates, and can be exchanged for rib samples, drinks, or other goodies at participating stations. Come hungry!

🔒 Exclusive for Ultimate Friend Badge Holders

One lucky Ultimate Friend will walk away with a genuine emerald—will it be you? Each $500 Ultimate Friend Badge includes a First Class Swag Bag containing a faux emerald... except one, which holds the real deal: a stunning [x]-carat emerald valued at $[xx], courtesy of Emeralds International (104 Duval Street).

On Sunday, August 31, before the Second Line Parade, badge holders are invited to stop by Emeralds International between 12:00 and 4:00 PM for a special reveal event. Have your gem inspected by the jeweler, enjoy light bites and mocktails, and snap a photo as you find out if you're the lucky one. This sparkling experience is available only to guests with the Ultimate Friend Badge. Don't miss your chance to add a little extra shine to your festival weekend.

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.

There’s no charge to attend, and the onsite full bar and snack bar will be open and ready to serve. Whether you’re lounging in the shade, floating in the water, or dancing to the beat, this is your chance 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.

Celebrate the life, music, and spirit of Key West’s favorite son, Jimmy Buffett, with us at the Second Line Memorial Procession—a joyful, tropical tribute filled with music, creativity, and community.

Whether you walk, cheer from the sidelines, or join virtually, this event welcomes everyone who holds a love for Buffett’s music and the island he called home.

The procession steps off promptly at 5:00 PM from the lower 100 block of Duval Street, parading five blocks down Duval, turning onto Southard Street for another five blocks, and ending at Truman Waterfront Park for a casual celebration. Expect live music, group singalongs, and lots of island-style fun along the way!

🎶 How to Participate:

Walk with us: Wear your brightest tropical attire, bring a colorful umbrella, decorate your bike, or carry a handmade sign or placard! Group themes and fun costumes are highly encouraged—show off your creativity and celebrate in true island style.

Play with us: Musicians are welcome and encouraged to join the procession. (Reach out to us if you want to coordinate!)

Watch along the route: Line Duval or Southard Street and cheer, sing, and share the moment.

Celebrate virtually: Host your own backyard or bar watch party and tune into the livestream!

🎟 Souvenir Event Badge:
Support the spirit of the Second Line and three great causes—Bahama Village Music Program, Reef Relief, and the Sister Season Fund—with the purchase of a $35 Event Badge. Badges are sold as a commemorative souvenir and can be purchased here ➔ www.justafewfriendskeywest.com
Purchasing a badge also gets you access to local perks and virtual participation options.

Full FAQ here ➔ https://www.justafewfriendskeywest.com/parade-pass-faq.

♻️ Our Commitment to the Cleanest Parade:
We’re proud to be designated the Cleanest Parade in Key West!
Our friends at Reef Relief will be marching with rolling trash cans and litter crews during the procession, but we encourage everyone to do their part—dispose of trash and recyclables properly and help us keep the island beautiful.

🚲 Getting Around:

Walking, biking, and ride share are highly recommended.

Metered parking is available but very limited near the start and end points.

The free Duval Loop shuttle is available from Truman Waterfront Park after the event.

Bikes can be walked in the parade and locked up at the park afterward.

💦 Stay Hydrated:
Bring a reusable water bottle! We’ll have free water refills available at Truman Waterfront Park thanks to the Florida Keys Aqueduct Authority.

🎷 What is a Second Line?
Originating in New Orleans and the Caribbean, a Second Line is a walking musical celebration where the community follows the band in joyful tribute. In Key West, it’s our heartfelt way to honor Jimmy—with music, laughter, tropical flair, and a few salty tears.

After the Second Line March winds its joyful way through town, the celebration continues at Party in the Park!Settle in for an easygoing evening filled with live music, local flavor, and island energy—designed to keep the festival spirit alive and celebrate Key West’s favorite son.

Throughout the night, enjoy performances by a rotating lineup including Nadirah Shakoor, Howard Livingston and the Mile Marker 24 Band, and special guest local musicians. Mixing it up with solo sets, collaborations, and surprise moments, it’s a laid-back, come-and-go gathering on the massive event lawn, perfect for kicking back and letting the island rhythm bring back nostalgic memories as you make new ones with just a few friends.

🎤 About the Artists:

Nadirah Shakoor—longtime Coral Reefer Band vocalist and former lead singer of the Grammy-nominated group Arrested Development—brings her soulful voice, vibrant stage presence, and deep connection to Buffett’s music to the stage.

Howard Livingston and the Mile Marker 24 Band, the Florida Keys’s beloved trop rock troubadour, are a true island treasure. A singer-songwriter who embodies the spirit of the Keys through storytelling and breezy, laid-back performances (and yes, he really lives at Mile Marker 24!). Howard may even fire up his vintage Johnson outboard motor on stage to craft his signature margaritas—a true island tradition!

Beyond the music, explore the Key West Artisan Market Island Time Market & Food Court, a lively hub featuring a curated collection of local artists, makers, and chefs. Browse handmade jewelry, tropical art, island-inspired gifts, boutique fashion, fresh bites, and more—all crafted by the creative spirit of the Keys.

You’ll also find full bars (featuring our official tequila sponsor Milagro Tequila), food trucks, and specialty drink stations scattered throughout the park.

And you won’t be able to miss the interactive art installations, colorful selfie stations, and the cooling bus courtesy of Key West Transit—perfect for a quick break between sets. Need to recharge? Head over to The Green House hospitality tent to chill out with the cool crowd under the misters, grab a seat, and enjoy a shady oasis close to the action. A charging station and free water (courtesy of the Florida Keys Aqueduct Authority—reusable water bottles encouraged!) will also be available to keep you refreshed and ready. Plus, don’t miss the spectacular sunset views over the Atlantic Ocean that promise to make this night even more unforgettable.

Grab a cold drink, sample delicious eats, shop a little, and find your spot on the lawn to soak up the tropical sounds. Whether you're dancing, shopping, relaxing, or just taking it all in, this is the signature event of the festival.

Come Monday, you’ll wish you could do it all over again.

As the music heats up at Party in the Park, take a stroll through the Key West Artisan Market pop-up!
Browse a vibrant collection of vendors, artists, crafters, and makers offering everything from tropical art and handmade jewelry to island-inspired gifts and goodies.

Enjoy delicious eats from food trucks, grab a refreshing drink from one of the festival bars, and soak in the festive waterfront atmosphere. Whether you're shopping for a souvenir, grabbing a bite, or just taking it all in between music sets, the Artisan Market adds another layer of fun to the biggest party of the weekend!

As the sun sets on Sunday, August 31st, the festivities continue at the Bubba After Party, starting at 8pm and going till we call it quits!

Following an unforgettable second line march and island tunes from Bubba's Stage at Truman Waterfront Park, keep the vibes going strong with more live music at Big Cheeezes.

And what's a party without some good eats? Indulge your taste buds with a feast fit for a beachcomber, featuring pizza, burgers, tenders, wings, and BBQ that'll satisfy your cravings and keep you fueled for a night of endless fun.

So kick off your flip-flops, let your hair down, and join us at the Bubba After Party for a laid-back, tropical celebration that'll make you feel like you're living life in a perpetual summer state of mind. It's a night of music, mingling, and munchies that you won't want to miss!