The Stove, The Tree, and The Track - Old Key West

The Stove, The Tree, and The Track

A Key West Story of Bars, Boats, and Bets

 

There are places in Key West where history is still visible.

And there are others where you have to listen for it.

Step into Captain Tony's Saloon and you’re standing inside one of the most layered buildings on the island. The hanging tree still stands inside—its roots tied to a time when the line between law and legend blurred.

That same building once housed the original Sloppy Joe's Bar before it moved to its current Duval Street location in 1937.

And then there’s Tony Tarracino—charter captain, later mayor, and one of the last true figures of old Key West. Stories follow him everywhere:

• Running boats to Cuba during the gambling years

• Moving through waters where not everything was declared

• Crossing paths with characters tied to organized crime from up north

In Key West, reputation often carried as much weight as record.

⚓ Down at the Harbor — Where the Working Crowd Gathered

A few blocks away, the story changed.

At Schooner Wharf Bar, history wasn’t preserved—it was lived.

Before it ever stood on land, the bar operated aboard the schooner Diamante, a floating gathering place for sailors, shrimpers, and harbor regulars. By 1986, it came ashore into the old shrimp dock buildings at the Key West Bight, right in the middle of a working waterfront.

This was a place built for:

• shrimpers coming off long runs

• sailors anchored off Wisteria Island

• deckhands still wet from spray and wind

And from those early dockside years, one detail still surfaces:

A small black stove in the corner
with a pipe running straight up through the roof

Not decoration. Just heat—for people who needed it.

🕺 Duval After Dark — The Real Order of the Night

 

Between Greene Street and the harbor, Duval had its own rhythm—and it changed by the hour.

The order of the night, as many remember it, wasn’t random.

It evolved.

First came places like The Monster—rooted in the 1970s into the early 80s—raw, loud, and loose, often described as one of the earlier true nightlife spots where things didn’t wind down early.

Then came The Copa, rising through the 1980s into the early 90s as Duval’s more defined dance club experience:

• music-driven

• packed late

• built for movement, not just drinking

Alongside those, but often a step off Duval’s main flow, were the local hangouts:

• Billie’s Bar & Restaurant — a true 70s and 80s era spot, remembered more for its regulars than its publicity

• P.T.’s Late Night — carrying into the 80s and 90s, known as a place where the night didn’t end when other doors closed

These weren’t tourist stops.

They were where locals went—before, after, or instead of the main strip.

And the same people moved between all of them.

A harbor worker could step off a boat, stop at Schooner Wharf…
drift through Duval…
and end up somewhere that never made a guidebook.

🐕 Out on Stock Island — The Track

 

Then there was Stock Island.

Close—but separate.

For years, the Key West Kennel Club operated a greyhound track there, part of Florida’s wider racing circuit that dated back to the 1930s. Night races brought in a mix of:

• fishermen

• mechanics

• service workers

• and anyone looking for something beyond Duval

It was structured—tickets, programs, betting windows—but still tied to the same island rhythm.

Stories passed around still mention:

• packed race nights

• steady betting action

• and big wins that stuck in memory

Including long-circulating accounts—never fully confirmed but often repeated—of figures like Captain Tony hitting significant payouts, sometimes said to be in the tens of thousands.

Whether exact numbers hold or not, the connection fits the time.

⚖️ When It All Shifted

By the late 1980s into the early 1990s, everything began to change.

• The shrimping industry declined

• The harbor transitioned into the Historic Seaport

• The nightclub era on Duval softened

• Greyhound racing across Florida began its decline

The Stock Island track closed during that period—its final days less documented than expected, but its disappearance part of a larger shift.

The crowd changed.

The island changed.

And the connections between these places began to fade.

⚓ KW Takeaway

You can still walk into Captain Tony’s and see the tree.

You can still stand at Schooner Wharf and look out over the harbor.

But there was a time when all of it connected:

a dockside stove
a Duval dance floor
and a racetrack under the lights

From The Monster… to The Copa…
from Billie’s… to P.T.’s…
from the harbor… to Stock Island—

That was Key West.