One Week From Today...

Jill Snodgrass
2 days ago
5 min read

2025 Just a Few Friends Second Line starting at Sloppy Joe's on Duval and proceeding to the Party in the Park at the Truman Waterfront.

ONE WEEK TO GO!

Hi Friends!

We are officially one week away from Just a Few Friends Key West!

If you’re already planning your visit, great—we can’t wait to welcome you. Take another look at the schedule, make sure you’ve reserved the experiences you don’t want to miss and let us know what else we can do to help you make the most of your time in Key West.

✅ YOUR MUST-ATTEND CHECKLIST

🍔 Thursday, September 3 · 5:00–8:00 PM Cheeseburger Beach Battle at Southernmost Beach Resort The tasting tickets are sold out, but $15 general admission is still available. Come for the live music, beachside fun and the chance to cheer on this year’s competitors.

🏝️ Friday, September 4 · 11:00–11:30 AM Key West’s Favorite Son City Proclamation at Shrimp Boat Sound Join us for this free proclamation ceremony honoring Jimmy Buffett in one of the places most closely connected to his Key West story. This will also be your first chance to shop the official event merchandise we’ll have for sale throughout the weekend.

🎶 Friday, September 4 · 5:30–9:00 PM Duval Street Party featuring Gary Roland & the Landsharks A free street concert on the 200 block of Duval, including the $1,000 Bubba Look-Alike Contest and a recreation of one unforgettable Key West music moment.

🍹 Saturday, September 5 · 2:00–5:30 PM Milagro Margarita Bar Strolls Choose the Duval Street route or Historic Seaport route. Tickets are $48, and there are still spaces available on both strolls.

🌅 Saturday, September 5 · 6:30–9:30 PM The Wheeland Brothers + Mike Stack & Friends at Sunset Pier Free music, a Key West sunset and one of the best waterfront settings on the island. What more do you need?

⛵ Sunday, September 6 · 10:00 AM–Noon Bubbles Brunch Sail with Will & Jessica Kimbrough aboard the luxury catamaran Argo Navis Start Sunday on the water with brunch and bubbles aboard one of Key West’s most beautiful sailing vessels.

🎺 Sunday, September 6 · 5:00–6:00 PM Second Line Memorial Walking Parade Free and open to everyone. Bring your placards and decorated parasols—or purchase a parasol from our merchandise tent—wear your tropical finest and walk with us from the 100 block of Duval Street to Truman Waterfront Park. Guests with mobility challenges may ride the complimentary Old Town Trolley.

🌴 Sunday, September 6 · 6:00–10:00 PM Party in the Park: Tribute to Bubba The parade leads straight into our free waterfront concert featuring Howard Livingston & the Mile Marker 24 Band, Will Kimbrough and Mac McAnally. Enjoy food trucks, Artisan Market shopping and a free Florida Keys Aqueduct Authority water-bottle filling station.

🥭 Monday, September 7 · 6:00–8:00 PM Come Monday: Cayman & the Mango Men at Sunset Pier Close out the waterfront portion of the weekend with another free Sunset Pier concert featuring early classics, Key West stories and plenty of island spirit.

🌙 KEEP THE PARTY GOING

Make plans to join us at all five free official after-parties:

Thursday · 9:00 PM–Midnight | Margaritaville Café with Nadirah Shakoor

Friday · 8:30 PM–12:30 AM | Hog’s Breath Saloon with Gulfstream tribute band

Saturday · 9:00 PM–Midnight | Back Yard EmPOURium with Claire Finley’s All-Star Jam

Sunday · 10:00 PM–Midnight | American Legion Post 168 with Aaron Luka’s “Songs We Know By Heart” Piano Sing-Along

Monday · 8:30–10:30 PM | Last Call at Smokin’ Tuna with Will Kimbrough

Looking for a more laid-back evening? Southernmost Pint Brewpub will host a free Parrot Heads documentary screening Friday and the Friends of Bubba Outdoor Video Lounge Saturday from 8:30–10:30 PM.

🌊 DON’T COME TO THE KEYS AND MISS THE WATER

If you haven’t scheduled at least one water excursion, now is the time. September is one of the best times to get out on the water—the water is warm and often gin-clear, and dolphin activity is plentiful.

Choose a Dolphin Watch & Snorkel Combo, R eef & Ritas snorkeling trip, Back Country Escape with Danger Charters, A Sailor’s Sun Sunset Sail aboard Argo Navis, Cruisin’ Tiki Sunset & Music Cruise or the Commotion on the Ocean Sunset Sail. There is something for every comfort level, and getting out on the water may become your favorite memory of the weekend.

🔍 FIND SOMETHING A LITTLE MORE PERSONAL

The big events are only part of the experience. Take another look at some of the smaller, more intimate ticketed offerings, including A Pirate Looks Back dine-in musical tribute show, guided plein-air painting at Shrimp Boat Sound and Louie’s Backyard, walking tours, the Coconut Telegraph Trolley Tour, the Shrimp Boat Sound: Echoes from the Edge movie and panel discussion, Sails Up: Intro to Sailing and more.

🏆 DON’T JUST WATCH—ENTER THE CONTESTS!

🕶️ Friday, September 4 · 6:30–7:15 PM Bubba Look-Alike Contest on Duval Street Think you—or someone you know—can channel Bubba? Enter the contest for a chance to win the $1,000 cash prize and become part of Friday night’s Duval Street show.

✏️ Monday, September 7 · Noon–1:30 PM Pencil Thin Mustache Contest at the Chart Room Start growing it, drawing it or dreaming it up now. This free Monday tradition is always one of the funniest events of the weekend and includes an incredible prize package with a weekend for two at the Pier House.

🧳 STILL ON THE FENCE?

There’s still time to make the trip, and rooms are still available at some great rates. And look into the Key West Express from Fort Myers for an easy, relaxed way to get to Key West.

Don’t sit this one out. Come for the music, the stories, the water and the memories—but most of all, come for the friendships.

We can’t wait to meet all our new friends and welcome back those who are returning. In just one week, we’ll all be together in Key West!

🌴 All are welcome · Come as you are · Be part of the story.

VIEW THE COMPLETE SCHEDULE

⛵🌅 Latitude Adjustment Sunset Sail

📅 Monday, September 7, 2026 ⏰ 6:00–8:30 PM 📍 Argo Navis · 0 Duval St, Key West

Join hosts Jill and Sean for a relaxed sunset sail aboard the 75-foot Argo Navis—an easy, elevated way to experience Key West from the water.

This all-inclusive evening is built for slowing down. Enjoy unlimited wines, craft beers, cocktails and non-alcoholic options, along with passed appetizers, all served by a top-tier crew as you take in the breeze and the view.

For Jill and Sean, this is more than just a sail—it’s one of their favorite ways to enjoy the island. As former crew members, with Sean still serving as a relief captain, they invite you to experience the water the same way: relaxed, unhurried and in good company.

GET TICKETS