Treasure Divers, Pot Smugglers, Beachcombers, Politicians..

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Florida Keys Road Trip | September 1, 2026

Hey Keys lovers! Labor Day weekend is coming, and Key West is about to spend five days remembering Jimmy Buffett in probably the most Buffett way possible: not with a quiet memorial, but with music, boats, bars, a second line up Duval Street, a pencil-thin mustache contest, and a free waterfront concert.

But before we get to this weekend, we need to go back to November 1971 and a tiny bar inside the Pier House.

Because there's still a sign hanging there that tells the story.

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❓ Keys Trivia

According to the sign inside the Chart Room, what was Jimmy Buffett paid to play there?

Answer at the bottom of the newsletter.

📣 The Mile Marker Roundup

🍔 Thursday: Back Where It Started
Just a Few Friends kicks off Thursday, September 3, and one of the first places that matters is the Chart Room at the Pier House — the tiny bar where Buffett played his first Key West gig. The weekend then gets rolling with cheeseburgers, beach music and Nadirah Shakoor, who spent years singing with Buffett and the Coral Reefer Band. See the full schedule →

🎸 Friday: Duval Gets Loud
Friday brings events around Shrimp Boat Sound, Buffett's old Key West recording studio, followed by music and the Bubba Look-Alike Contest. There is money on the line for looking like Jimmy Buffett, proving once again that America remains a land of opportunity. See Friday's events →

🍹 Saturday: Don't Skip the Seaport
Saturday may be the sleeper day. There are events all over town, but we'd leave room for wandering around the Historic Seaport. Duval will find you eventually. Spend an afternoon around the working waterfront, talk to bartenders, look at boats and see where you wind up. That's usually a better Key West plan than an actual plan. See Saturday's schedule →

🎺 Sunday: This Is the One
At 5 p.m., the Second Line Memorial Walking Parade steps off in the 100 block of Duval and heads toward Truman Waterfront Park. Then from 6–10 p.m., the free Party in the Park brings Mac McAnally, Will Kimbrough, and Howard Livingston & the Mile Marker 24 Band to the waterfront. If you only have one day, we'd make it Sunday. See Sunday's schedule →

🥸 Monday: Come Monday... There's a Mustache Contest
Labor Day lets everybody down gently with more music, sails and a Pencil Thin Mustache Contest at the Chart Room before Cayman & the Mango Men help play the weekend toward sunset. After five days in Key West, a mustache contest may actually seem perfectly reasonable. See Monday's events →

🌴 Partner Spotlight

Still Need a Place to Stay?

If you're making a last-minute run to Key West for Labor Day weekend, staying in Key West itself will make this one much easier. Most of the action is concentrated around Old Town, Duval Street and the waterfront.

FloridaKeysResorts.com can help you compare places to stay across Key West and the rest of the island chain.

See Florida Keys resorts →

🧩 Deep Dive

The Sign Inside the Chart Room

November 1971.

Inside the Pier House in Key West is a little bar called the Chart Room.

It's still there.

And hanging inside it today is this sign:

NOVEMBER 1971

CHART ROOM BAR

JIMMY BUFFETT'S FIRST KEY WEST GIG

Then comes the good part.

The sign says Jimmy fell in love with Key West while playing for free drinks, right there in the Chart Room, for:

“Treasure divers, pot smugglers, beachcombers, politicians and friends!”

There may never have been a better one-sentence description of Key West.

Buffett was new in town.

Margaritaville didn't exist.

There were no Margaritaville resorts. No restaurants. No stores. No empire.

Just a songwriter, a little bar and free drinks.

He didn't stay a nobody.

But here's the part of the story we like.

He paid attention.

He noticed Fausto's.

He noticed Captain Tony's.

He noticed the Chart Room.

He noticed the people living around him — sailors, bartenders, fishermen, dreamers, drunks, pirates real and imagined, and assorted characters whose résumés probably improved considerably in the retelling.

And he wrote them down.

That's important.

Because Buffett didn't invent some perfect tropical island and then spend his career trying to sell it to everybody.

He had Key West sitting right in front of him.

He used the names.

He used the streets.

He used the characters.

He even used the grocery store.

Anybody could have walked past those places.

He wrote them down.

That's the whole trick.

And maybe that's why those songs still sound like somewhere.

He didn't just write about paradise.

He wrote about the grocery store.

🎶 Three Years Later, Key West Throws a Party

Jimmy Buffett died September 1, 2023.

Three years later, almost to the day, Key West isn't holding the sort of memorial where everybody sits quietly in folding chairs.

That would be suspicious anyway.

Instead, Just a Few Friends runs September 3–7, 2026.

Five days.

Music.

Boats.

Bars.

Stories.

Cheeseburgers.

People dressed like Buffett.

People who look like Buffett without meaning to.

And on Sunday afternoon, everybody pours onto Duval Street.

The Second Line

At 5 p.m. Sunday, the Second Line Memorial Walking Parade steps off from the 100 block of Duval.

This matters because a second line isn't really something you watch.

You join it.

There will be musicians.

There will be photographs.

There will be costumes.

There will be singing.

There will undoubtedly be at least one person who began preparing his outfit sometime around Easter.

The procession moves up Duval and eventually reaches Truman Waterfront Park.

And that's where the weekend hits its high point.

🎸 Party in the Park

Sunday, September 6
6–10 p.m.
Truman Waterfront Park

FREE

Onstage:

Mac McAnally

Will Kimbrough

Howard Livingston & the Mile Marker 24 Band

Outside.

On the water.

At sunset.

Free.

There are sentences that don't require much additional salesmanship.

That's one of them.

See the complete Just a Few Friends schedule →

🍹 Four Things We'd Tell a Friend

Book the room now.

At this point we're no longer in the thoughtful vacation-planning portion of the program.

We're in the Does it have air-conditioning? Fine, take it portion.

If you only come for one day, make it Sunday.

Second line at five.

Party in the Park at six.

That's the heart of the weekend.

Don't overlook Saturday.

Everybody will photograph Sunday's parade.

But Saturday afternoon wandering around the Seaport, stopping at bars and talking to people may wind up being your favorite part.

That's how Key West works.

The thing you didn't schedule has an irritating habit of becoming the thing you remember.

And pace yourself Thursday.

This festival lasts five days.

The rum supply does not require your personal assistance.

Key West has this handled.

❤️ Buy the Badge

There is also a collectible Just a Few Friends badge.

It isn't your admission ticket to the whole weekend — many of the major events are free.

It's the charitable side of the celebration, with proceeds supporting local causes.

So if you're coming down anyway, buy one.

Buffett spent a lifetime getting something from Key West.

He also spent a long time giving back.

That's a tradition worth keeping.

Learn about the festival and badge →

🕰️ Lore & Legends

You Can Still Walk Through His Key West

This may be the best part.

So much of Buffett's Key West is still here.

The Chart Room is still inside the Pier House.

The Pier House still stands at the foot of Duval.

Fausto's Food Palace is still a grocery store.

Blue Heaven is still serving people beneath the trees.

Captain Tony's Saloon is still Captain Tony's.

And Duval Street remains Duval Street, despite several million people's best efforts to leave it slightly worse than they found it.

You can walk between these places.

That's what makes this weekend different from visiting the birthplace of somebody famous and finding a plaque attached to a bank.

The geography survived.

You can have a drink in the room.

You can walk the streets.

You can buy something at the grocery store.

And for a few days this weekend, thousands of people will be doing exactly that.

✅ Trivia Answer

Free drinks.

That's what the sign inside the Chart Room says.

In November 1971, Jimmy Buffett played there for free drinks in front of:

Treasure divers.

Pot smugglers.

Beachcombers.

Politicians.

And friends.

Although, knowing Key West, those categories probably overlapped.

If you're going to be on the island this weekend, hit reply and tell us which day you're coming for.

We'd like to run into you.

And if you're not coming, do this instead.

Sometime Sunday evening around six, put on A1A.

Pour something cold.

Sit outside if you can.

And think about thousands of people walking up a street in Key West singing songs written by a guy who arrived here 55 years ago and bothered to notice what was around him.

The bar.

The characters.

The boats.

The grocery store.

There's a lesson hiding in there.

The places that matter aren't always the famous ones.

Sometimes they become famous because somebody paid attention.

Pay attention to where you are. Someday it may be a song.

Until next week, keep your windows down and your watch off.

The Florida Keys Road Trip Team

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