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.

Sean K is your guide along with Carol Shaughnessy, who has been part of the Key West story for decades. When her longtime partner, Phil Clark — the free-spirited sailor who inspired Jimmy Buffett’s classic “A Pirate Looks at 40”— fled the island with the law on his heels, the course of her life changed. Carol later helped launch the original Margaritaville Store and its "Coconut Telegraph," putting her right in the heart of the island’s music and storytelling era. Today, she shares that rich history with visitors, connecting the dots between Buffett’s Key West and the characters who brought his songs to life.

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! ⛵🥂🌞

From the author of Buffett Backstories: 50 years, 50 songs comes an all new Buffett Backstories: Pirate Edition. You might recall a certain Key West local and Chart Room bartender named Phil Clark who was immortalized in song by Jimmy Buffett. But "A Pirate Looks at Forty" belies Clark's privileged past. Following exhaustive research by author Scott Atwell, stories of Clark’s life emerge in fascinating detail about a New York sophisticate who sailed off to the lower latitudes of the globe, where pirates once roamed, and reinvented himself on an island. Not in a good way, but a memorable one. If we looked closely enough, scattered clues would have led us to the story's conclusion, like an "x" on the map. This is the true tale of the Pirate, Phillips Clark.

Join Atwell on Sunday, August 31 from 11 am to 1 pm at Books & Books (Judy Blume's famed book store) where you can pick up a copy or two and get it autographed on the spot.

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 0.73 cts genuine emerald valued at $2,300—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 0.73 carat emerald valued at $2,300, 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 5:00 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 with an unplugged version of Margaritas in Paradise Jimmy Buffett Tribute Band, 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 gathers starting at 4pm, 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!

Look for fun stops en route at Sloppy Joes and the Greeen House

🎶 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 Key West High School Marching Band —with the purchase of a $45 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.

Check out the Full FAQ here!

♻️ 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.

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!

Vendors Include

·       123 Lock and Key: Local mobile locksmith at your service

·       Authentic Hemp Company: Nourishing and vibrant botanical products to support your active lifestyle

·       Bath Fitter: Bathtub/Shower Remodeling info

·       Beached Bum Life: Beached Bum Life delivers coastal cool with patented Phone Koozies, sand-proof towels, and hidden-pocket magic—engineered for effortless vibes and beach days done right.

·       Booze Bandage: Booze Bandage offers all-natural B1 vitamin patches designed to help you party smart and wake up clear—no hangover, no hassle.

·       Danubio Fashion: Crochet clothes and jewelry made of forks and spoons

·       Dawgone 'Licious: Dog treats designed with your dog in mind! A dog treat bakery

·       Doner on Wheels: Serving the best gyro in Key West

·       Duetto Pizza and Gelato: Pizza by the slice

·       Eaton Bikes Key West: Friendly service and bike rentals

·       Florida Keys Aqueduct Authority: Free water refill station

·       Frayed Threads LLC: Women's Italian linen apparel

·       Ginger Voodoo: Organic, handmade bath and body by a mother–daughter team on a mission to keep it chemical-free and healing.

·       Island Stone and Design: Handcrafted, one of a kind, useful art. Rod holders, outdoor furniture etc.

·       iWEAR...do you?: Handmade industrial, gemstone & fashion jewelry + original art - framed prints, prints & greeting cards

·       Just a Few Friends: Info booth

·       Joey's Mini Donuts: Mini Donuts made to order. Hot! Fresh! Delicious!

·       Key West Flags: All things Conch Republic.

·       Key West Organics: Organic Body Care infused with Island Soul

·       Key West Spice Company: Key West Spice Co. is a woman-owned brand bottling the bold, breezy flavors of the Florida Keys with tropical spice blends that taste like sun, sea, and Southern charm.

·       Key West DoT: Free public cooling station on a City of KW bus

·       Macdoobbq: Pulled pork, brisket, ribs, sausage, Mac n cheese, beans, cornbread soufflé

·       Mavka Permanent Jewelry: Custom design and fit permanent jewelry that will commemorate your wonderful time in Key West!

·       Mile Zero Enterprise: On-site chair rentals

·       Rachel Burrows Art and Jewelry: Handmade Boho Beach jewelry also acrylic paintings and shell art.

·       Reef Relief: Reef Relief is a non-profit that protects our marine environment through education and conservation.

·       Salsa y sabor baking goods: We sell different types of delicious artisan breads and dips. We also have delicious nut butters and jams.

·       Southernmost Concessions: Fresh squeezed lemonade and key limeade, Kettle corn in multiple flavors, funnel cakes, and pork rinds.

·       Sugar & Sand Candle Co: Custom hand-poured soy wax candles

·       Tarot card reader: Tarot card readings onsite

·       The Greeen House: No Medical Card Needed. Money Back Guarantee.

VENDOR APPLICATIONS are being accepted for culinary, food trucks, artists, crafters and merchants. Click here to submit your application!

After the Second Line March winds its joyful way through town, the celebration continues at Party in the Park presented by our friends at the Greeen House! 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.

𝐖𝐞𝐥𝐜𝐨𝐦𝐞 𝐋𝐮𝐜𝐲 𝐁𝐮𝐟𝐟𝐞𝐭𝐭! After leading the Second Line March, we're excited to bring Lucy to the stage to welcome guests and share a few heartfelt words as we kick off Party in the Park—an evening filled with music, memories, and the island spirit her brother helped inspire. Her presence adds a personal touch to a celebration rooted in friendship, storytelling, and the rhythms of Key West.

🎤 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!

𝐉𝐨𝐜𝐤𝐞𝐲 𝐉𝐨𝐫𝐝 is a Key West-based singer-songwriter known for his soulful voice, laid-back style, and heartfelt performances that channel the spirit of island life. With roots in coastal Americana and trop rock, his original songs blend storytelling with breezy rhythms and a touch of Gulf Coast grit. A regular on the Key West music circuit, Jockey Jord has become a festival favorite for his warm stage presence and deep connection to the music and the moment.

Beyond amazing performances in tribute to our favorite troubadour there's plenty more to enjoy in the park:

❥ Sip & Savor: Grab an adult beverage at the Great Events bars Cash and credit accepted. (please, no outside beverages or coolers permitted)

❥ Chill Out: Relax with the cool crowd at the Greeen House hospitality. The Greeen House, title sponsor of Party in the Park, is your “home away from home” for premium THC products—no medical card needed. Known for their massive selection, expert staff, and 100% satisfaction guarantee, they’re here to help you find your perfect vibe while you’re in town. Must be 21+ to enter. Come see what the BUZZZ is all about!

❥ Rent-a-chair: Mile 0 Enterprise will have over 400 bag style chairs for rent at $9 each CASH ONLY. Use them during the event and they'll pick them up at the end. BYOC (bring your own chair) is also permitted.

❥ Taste the Flavors: Enjoy a delicious bite from our vendors & food trucks in the then treat yourself to a sweet dessert!

❥ Shop & Stroll: Explore the offerings from local makers, artists and curators at the mini Key West Artisan Market. Be sure to pick up a unique piece of art or souvenir—merchants are happy to hold your purchases until you're ready.

❥ Catch the Sunset: Experience the awe-inspiring sunset, a must-see sinking into the ocean at 7:46 pm.

❥ Stay Hydrated: Refill your water bottles for FREE at the Aqueduct Authority.

❥ Cool Off: Visit the super air-conditioned City Bus to relax and unplug.

❥ Strike a Pose: Visit selfie/photo stations featuring the Friends of Bubba Stage backdrop and the Southernmost Inflatable Buoy and get free photos direct to your inbox. Don't forget to share your shots with #justafewfriendskeywest.

❥ Honor the Memory: Bring a photo, note, or small memento and light a free candle at the Friends of Bubba Memorial. Items will be collected and honored in a special exhibit celebrating the memories we shared.

❥ Give Back: Throughout the evening, you’ll have the chance to donate to our valued charities: Reef Relief, the Bahamas Village Music Program and the Key West Hight School Band. Representatives will be on-site to show you how your contributions matter.

❥ Take the Bus: The Duval Loop will be operating after the event to drop you at various locations including the after party for $1.

❥ Radio Trop Rock and Key 93.7 Yacht Rock broadcasting live

❥ Don't miss the After Party: The Backyard Bar at Kaya Island Eats is host to our Bubba's official after party featuring the Caribbean steel pan twists on your Jimmy Buffett favorites. No cover, kitchen open until 10pm.

We've put together a comprehensive FAQ to help

👉 https://www.justafewfriendskeywest.com/event-faq

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

As thAs the sun dips below the horizon on Sunday, August 31, keep the weekend vibes alive at the Bubba After Party in the laid-back backyard of the Key West Emporium. The party kicks off at 8:30 pm and goes late—until the island says enough!

Feel the rhythm with local favorite Toko Irie and the New Beginning Band as they light up the night with a Caribbean soundtrack: steel drums, soca, reggae, kompa—and plenty of Buffett-inspired grooves. Add in Milagro drink specials, and you’ve got yourself a true island jam.

Hungry? Kaya Island Eats will be serving a full menu until 10 pm—perfect fuel for dancing under the stars.

So toss off your flip-flops, loosen up, and join us for a tropical late-night celebration where the music is hot, the drinks are cold, and the summer never ends. Good tunes, good company, and good eats—Key West style.e sun dips below the horizon on Sunday, August 31, keep the weekend vibes alive at the Bubba After Party in the laid-back backyard of the Key West Emporium. The party kicks off at 8:30 pm and goes until the island says enough!