Capt Tony’s Saloon

Bar · Key West

5

@atlasobscura

Captain Tony's Saloon – Key West, Florida - Gastro Obscura

"Most trips to Key West involve a visit to its most famous bar on Duval Street, Sloppy Joe’s, but for those who would like a little literary history and a whole bunch of morbidity with their cocktail, the “Sloppy Joe’s” where Ernest Hemingway used to sit and drink is right around the corner on Greene Street, now known as Captain Tony’s Saloon. Josie Russell opened Sloppy Joe’s on Greene Street in the 1930s, and in 1938 when the rent was raised by a dollar a week, the bar moved to its more famous location on Duval. The building that was once Hemingway’s watering hole went through several incarnations before finally being purchased by Captain Tony Tarracino and Captain Tony’s saloon was born. The building itself has a long and macabre history, stretching back to the early nineteenth century. Visitors will notice that inside the bar is a large tree- this was the gallows tree in the open courtyard that was used for judgements, and the building was later built around it.  At least 75 people were hung here for piracy, along with other transgressors. Ironically, the tree itself is still alive; it extends through the roof, though Hurricane Irma took much of the top, at least six inches of tree still peek above the building. Curiously, it still sprouts twigs and leaves inside the dusky bar. In its storied past, the building saw time as a morgue, a bordello, a telegraph office, a speakeasy and a cigar factory. During refurbishing work in the 1980s, the floorboards were taken up to reveal the bones of between 15-18 people. Among them, a gravestone for a young woman named Elvira Drew was discovered. Elvira was married, in her mid-teens, to an abusive, alcoholic man in his fifties. Elvira left the world in 1822 at the tender age of 19, hanged on winter solstice nearly two hundred years ago for killing her husband- self-defense wasn’t a valid argument at the time. Her tomb marker now sits beside the pool table for eternity, or at least until the bar undergoes another renovation. Another gravestone in the bar underneath the old hanging tree belongs to Reba I. Sawyer, a Key West native who lived from 1900 to 1950. Upon her death, her husband found scandalous letters between his wife and another man. The letters detailed their trysts, and how they would arrange to meet at Captain Tony’s Saloon. The widowed husband dragged his cheating partner’s tombstone from the cemetery into the bar, placed it under the tree, and supposedly said “this is where she wanted to be, so this is where she will stay”. There are far more bodies under the floor than there are gravestones- some graves are flush with the current floor level, and some rest beneath it. So wherever you step, you’re walking on someone’s grave. And before you leave, make sure to say goodbye to the resident skeleton, now propped up and fashionably dressed inside the bar. Know Before You Go Down the street from the famous Sloppy Joes." - annakovach, Louchebonvivant, Shaheen Alikhan, Luke J Spencer, Collector of Experiences, s scottburau, Molly McBride Jacobson, Rachel, scottburau

https://www.atlasobscura.com/places/captain-tony-s-saloon

428 Greene St, Key West, FL 33040 Get directions

capttonyssaloon.com

5 Postcards

See full details

More Places For You

Garbo's Grill @ Hanks!

Restaurant · Key West

Garbo's Grill is a beloved Key West food truck serving up inventive tacos, burgers, and more in a laid-back setting framed by live music and vibrant outdoor seating.

2 Postcards

Chelsea House Hotel in Key West

Hotel · Key West

Nestled in three charming Victorian homes, this cozy hotel offers a relaxed vibe with comfortable rooms, a lovely pool, and free breakfast just steps from Duval Street.

0 Postcards

Southernmost Point of the Continental U.S.A.

Historical landmark · Key West

Marking the continental U.S.'s southernmost point, this iconic red-and-black buoy in Key West is a must-photo spot just 90 miles from Cuba.

6 Postcards

Ocean Key Resort & Spa

Resort hotel · Key West

Ocean Key Resort & Spa is a vibrant, island-style getaway on Duval Street offering chic rooms with balconies, an inviting pool, a superb spa, and unmatched sunset views from the lively Sunset Pier, making it the perfect base to soak in all the Key West excitement.

4 Postcards

B.O.'s Fish Wagon

Seafood restaurant · Key West

A funky driftwood shack serving fresh, fried fish sandwiches, conch fritters, and beachy bites with laid-back Key West vibes.

5 Postcards

Thirsty Mermaid

Seafood restaurant · Key West

Nestled on a charming corner in Key West, Thirsty Mermaid serves up a delightful blend of fresh seafood, creative bites, and craft drinks in a cozy, nautical atmosphere.

2 Postcards

Ella's Cottages - Key West Historic Inns

Inn · Key West

Ella's Cottages offers laid-back charm with cozy rooms and lush gardens, just a block from bustling Duval Street, making it an ideal Key West retreat.

1 Postcard

Salute! On The Beach

American restaurant · Key West

Salute On The Beach is a laid-back, beachside gem serving tasty Italian seafood dishes and famous Key Lime pie with stunning ocean views.

1 Postcard

The Bull

Bar · Key West

Nestled on Duval Street, this lively three-level bar serves potent drinks amidst murals and music, perfect for people-watching and lazy afternoons.

1 Postcard

Sloppy Joe's Bar

Bar · Key West

Step into Sloppy Joe's, the iconic bar that’s been rocking Key West since 1933, where you can dance to live music, sip frozen drinks, and savor the lively atmosphere.

5 Postcards