The President Who Ran the Country From Key West

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Florida Keys Road Trip | November 11, 2026

Hey Keys lovers! Happy Veterans Day.

If you are in the Keys today, there is a ceremony within a short drive of wherever you are standing, and this afternoon Key West puts a parade on Duval Street.

It is a Navy town. It has been for a very long time.

The island has a Navy base, a Navy cemetery plot, a street named for a president who loved the place, and a white house on the old naval station where that president ran the country with his shirt untucked.

This week we are going to tell you about all of it.

And to everybody reading this who served: thank you.

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❓ Keys Trivia

You have almost certainly driven down Truman Avenue in Key West.

Before 1948, it had a different name.

What was it?

Answer at the bottom of the newsletter.

📣 The Mile Marker Roundup

Veterans Day up and down the chain today, a fishing tournament this weekend, and movies next week.

North to south.

🇺🇸 MM 102, Key Largo: Veterans Day ceremony Today at 11 a.m. at the Murray Nelson Government Center.

🇺🇸 MM 82, Islamorada: Veterans Day ceremony Today at 11 a.m. at Islamorada Fire Rescue Station 20, 81850 Overseas Highway.

🇺🇸 MM 50, Marathon: Veterans Day parade Today at 11 a.m. The parade starts at 20th Street and ends at American Legion Post 154, 4115 Overseas Highway, with a ceremony at the post around noon. Small-town parade, big-hearted crowd.

🇺🇸 MM 0, Key West: Ceremony and parade The ceremony is at 11 a.m. at the Veterans Memorial Garden in Bayview Park. The parade steps off on Duval Street at 4 p.m. Expect Duval closed that afternoon, and expect it to be worth it.

🎣 MM 17, Sugarloaf Key: The Sugarloaf Showdown Thursday through Saturday, November 12 to 14. A backcountry tournament for bonefish, permit and barracuda. If you see people standing perfectly still on the front of a flats skiff this weekend, they are working. See the schedule →

🎬 MM 0, Key West: Key West Film Festival The 15th annual festival starts Wednesday, November 18, and opens with Paper Tiger, starring Miles Teller, Adam Driver and Scarlett Johansson. There is also a new Florida series, including a world premiere about the real man behind a character in Jaws.

🦀 The whole chain: Stone crab season Still on, and still the best reason to stop at a fish house on the way down. Ask what came in today.

🌴 Partner Spotlight

The Two Weeks Before Thanksgiving

Here is a window most people miss.

Race week is over. Thanksgiving is two weeks away, and the winter crowds start the week after that.

Right now the Keys are warm, quiet and wide open. Restaurants have tables. The water is still warm enough to swim. The light in the late afternoon goes gold early and stays that way.

And if you are thinking about Thanksgiving itself in the Keys, now is the time to look, not the week of.

FloridaKeysResorts.com can help you compare places to stay from Key Largo to Key West, with nobody taking a commission out of the middle.

See Florida Keys resorts →

🧩 Deep Dive

The Little White House

In November 1946, a doctor told Harry Truman he needed rest and sun.

He picked Key West.

He stayed in a white frame house on the Navy base, built in 1890 as the first officers' quarters on the naval station. The house had already done a tour of duty. During World War I, Thomas Edison lived there for about six months while he worked on underwater weapons for the Navy.

Truman liked it so much he kept coming back. Eleven visits over the course of his presidency. A hundred and seventy-five days in all.

People in Washington complained that the President was off in Florida on vacation.

His answer was that wherever the President is, the White House is. And he meant it.

So the house became the Little White House.

Real work got done there. Cabinet members flew down. In March 1948, the military chiefs met on the base for four days and worked out the basic shape of what became the Department of Defense. It is still called the Key West Agreement.

There were also a lot of poker games. And a lot of loud shirts.

When Truman won the 1948 election, the one almost everybody said he would lose, the town renamed one of its main streets in his honor.

He was not the only one who liked the place. William Howard Taft was the first president to visit it. Dwight Eisenhower came down as president to rest. John F. Kennedy held a one-day summit there with the British prime minister in 1961.

Today it is a museum, restored to how it looked in 1949. His desk. His rooms. His poker table.

It sits inside Truman Annex, a short walk from Duval and Mallory Square, which means you can be standing in the room where the Department of Defense was sketched out about ten minutes after you finish your lunch.

On Veterans Day, it is the right place to start.

🍹 Four Things We'd Tell a Friend

Go to a Veterans Day ceremony, even if you are on vacation.

They are short, they are local, and the people there will be glad you came. Every town on the chain has one today.

Tour the Little White House.

The guides are good, and the poker table alone is worth the price. Leave the car somewhere else. You are walking distance from everything.

Walk the Key West Cemetery.

It is free, it is right in the middle of Old Town, and it is one of the strangest and most interesting places on the island. More on that below.

Look at Thanksgiving now.

It is two weeks out. If you want to spend it with your feet in the water instead of at the kids' table, this is the week to plan it.

📖 One More Thing

Lost in the Keys: Mile Marker Thoughts is out.

It is about this drive. The bridges, the bars, the stops you mean to make and the ones you make by accident, and what goes through your head on a road that is mostly water.

If you have read it, a review helps more than you would think.

Get the book → Lost In The Keys

🕰️ Lore & Legends

The Sailors Who Came Home to Key West

On the night of February 15, 1898, the battleship USS Maine exploded in Havana Harbor, about ninety miles south of Key West.

Most of her crew died. It became the spark for the Spanish-American War, and "Remember the Maine" became the slogan of the year.

Key West was the closest American port.

Some of those sailors were brought here. Twenty-four of them are buried in the Key West Cemetery, in a plot of their own, inside an iron fence that was brought down from Washington, D.C.

A monument stands over them. Built into it is a piece of the ship herself, part of the Maine's fire control turret.

The plot is still tended. The flags are still changed. On Memorial Day and Veterans Day, people still come.

And the cemetery around it is one of the most Key West places in Key West.

It was laid out in 1847, right in the middle of what is now Old Town. The city estimates something like seventy thousand people are buried there, which is a lot more people than live on the island today. Because the ground is solid coral rock and the water table is high, many of the graves sit above ground, stacked in vaults.

Wander a little and you will find the epitaphs that made it famous.

Pearl Roberts, who passed in 1979, has a stone that reads: I told you I was sick.

Another reads: I'm just resting my eyes.

It is a quiet, sunny, slightly funny place, with a corner that is very serious.

The cemetery is free. The entrance and office are at Passover Lane and Angela Street, and the office has free walking tour guides on weekdays.

Find the Maine plot first.

Then go read the headstones.

✅ Trivia Answer

Division Street.

It was renamed Truman Avenue shortly after Truman's surprise win in the 1948 election, in honor of the president who kept coming back.

If you served, hit reply and tell us where and when. We would like to say thank you properly, and a few of your stories may show up in a future issue, with your permission.

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

The Florida Keys Road Trip Team

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