READY TO RUN, WALK, STROLL—OR FLOP FOR MARGARITAS?
Start your Labor Day weekend island-style with the 2nd Annual Parrots and Margaritas 5K and Flip-Flop Mile—organized by our friends at Mile 0 Events and hosted at the iconic, everyone’s favorite sing-along bar, Irish Kevin’s!

Choose between the full 5K or the easygoing Flip-Flop Mile. The Flip-Flop Mile is just 3/4 of a mile but still full of fun. Skip the sweat and grab the swag—then strut your stuff past Shrimp Boat Sound Recording Studio and head straight to the finish line celebration.

Then everyone celebrates the finish with a lively post-race party featuring margaritas, cheeseburger sliders, tropical tunes, and island camaraderie.

ALL PARTICIPANTS RECEIVE:
👕 Event T-Shirt
🍹 Souvenir Margarita Glass
🎟️ 1 Free Margarita, Landshark Beer, or Soft Drink
🎉 Post-Race Party Entry at Irish Kevin’s
🍔 Free Post-Race Food: Cheeseburger Sliders & Tater Tots

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.

Join us for a special author signing event featuring renowned Key West photographer Ralph DePalma, whose stunning images of Jimmy Buffett have captured the essence of his legendary performances and island spirit. Ralph, known for his acclaimed coffee table books celebrating Key West’s vibrant music scene, will showcase exclusive photos of Buffett featured in his latest work. Fans will have the opportunity to meet the photographer, hear behind-the-scenes stories, and get signed copies of his book—a must-have keepsake for any Buffett enthusiast. Don't miss this chance to celebrate Jimmy’s legacy through the lens of a true island storyteller!

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!

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.

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.

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.

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.

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.

Join us for an extraordinary evening on Sunset Pier at the Ocean Key Resort & Spa, where you can enjoy a free live music event while witnessing Key West's legendary sunset.

🎤 Live Music Featuring The Nautical Wheelers: A Tribute to Jimmy Buffett. Enjoy an exceptional performance by Roger Bartlett, the original guitarist of Jimmy Buffett's Coral Reefer Band, alongside Jockey Jord, Claire Finley and Emily Randle. Relive the magic of classic hits with musicians who know how to capture the essence of paradise.

🌅 Breathtaking Views. Sunset Pier offers the best seat in town for unparalleled views of the stunning Key West sunset.

🦞🍹 Delicious Seafood and Drinks. Indulge in mouthwatering culinary delights and refreshing drinks at our relaxed dockside eatery.

🎶 Daily Live Music. Experience live music performances every day, enhancing the vibrant atmosphere of Sunset Pier.

📹 Can't Make It? No worries! You can still catch the show via Ocean Key's Sunset Pier Webcam: https://www.oceankey.com/key-west-sunset-pier/

About Roger Bartlett:
Roger Bartlett is not just any musician; he's the original guitarist of Jimmy Buffett's Coral Reefer Band. In the early days, it was just Jimmy and Roger captivating audiences with their acoustic guitars and vocals. Following the success of “Come Monday,” the duo expanded into a full band to accommodate their growing fanbase. Roger is also known for his song “Fool for a Blonde” from the classic horror movie The Texas Chainsaw Massacre, and his extensive career with various bands and as a lead guitarist for many artists across the country.

Don’t miss this chance to be part of a magical evening filled with great music, stunning views, and unforgettable memories. See you at Sunset Pier!

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.