Wonder Which are the Best Bars in Key West – You’ll Love This One

When you think of Key West the first things that comes to mind are:

  • Ernest Hemingway
  • Drinking
  • Pirates and Treasure Hunting

Ernest Hemingway’s presence is everywhere. Especially in the bars that were rockin’ over 80 years ago, as they are now.

Sloppy Joe’s and Captain Tony’s the top two best bars in Key West and must visit when staying on Key West. Ironically enough, Sloppy Joe’s original location is where Captain Tony’s Saloon is located now.

Key West, Florida- Captain Tony's Bar -  doorway

But Captain Tony’s bar is not only legendary for it’s history but also for it’s design.

Key West, Florida- Captain Tony's bras everywhere

History of Capt Tony’s Saloon

  • It is a Landmark of Key West and National Treasure since 1851.

  • It used to be one of the favorite watering holes of legends like: Ernest Hemingway, Truman Capote, Tennessee Williams, Shel Silverstein and Jimmy Buffet.

  • The building where it stands was built in 1851 as an icehouse.

  • It also doubled as a morgue before electric refrigeration was invented.

  • The saloon is also the home of Key West’s ‘Hanging Tree.’  This infamous tree was used to hang 17 people until death; 16 convicted pirates and one woman who stabbed to death her husband and two small children.

  • People say that her spirit haunts the saloon to this day.

  • This location became a cigar factory in 1912.

  • In 1933, a local Conch, named Joe “Josie” Russell opened Sloppy Joe’s here.

  • Ernest Hemingway frequented Sloppy Joe’s during this time.

  • In 1938, Josie Russell, in a dispute with the landlord of 428 Greene Street over a $1 rent increase decided to move the entire bar in the middle of the night.

  • In 1940, 428 Greene Street’s landlord leased the building to Morgan Bird, who opened the saloon as the Duval Club.

  • 1958 brought the most recent chapter to 428 Green Street, when Captain Tony bought the bar from David Wolkowsky. Captain Tony’s Saloon has been thriving in that location ever since.

Key West, Florida- Captain Tony's Bar - entrance

Who is Captain Tony?

  • His actual name was Anthony Tarracino.

  • He was born in Elizabeth, New Jersey.

  • He was a ninth grade dropout that made whiskey, illegal at the time due to Prohibition, became a gambler and got involved with the New Jersey Mafia who moved to Key West I 1978.

  • In Key West he became a shrimper, charter boat captain, a gunrunner and in 1958, he opened and became the proprietor of Captain Tony’s Saloon.

  • Captain Tony ran for mayor of Key West four times before winning office in 1989.

  • He was the father of thirteen children by five wives.

  • Until his passing in 2008, Captain Tony was a regular fixture at the saloon.

  • His motto was: “All you need in this life is a tremendous sex drive and a great ego, brains don’t mean a shit.”

Ernest Hemingway’s Influence on Key West Drinking and Bar Scene

  • Ernest Hemingway’s watering holes is that his favorite bar, owned by his good friend, Josie Russell was “Sloppy Joe’s” (it used to be where Captain Tony’s Saloon is now.

  • Most of Hemingway’s productive years as an author took place in Key West during this time (1928-1938).

  • He met his circle of friends every afternoon at 3:30 – at Sloppy Joe’s Bar (Captain Tony’s Saloon).

  • Ernest Hemingway and his second wife, Pauline, came to Key West from Paris in 1928 on the advice of John Dos Passos, a novelist.

  • Hemingway’s boat captain and favorite bar owner, Josie Russell cashed a $1,000 royalty check for Hemingway when a bank refused and they became close friends.

  • Russell and Ernest Hemingway would leave Key West for extended fishing trips to Havana.

  • Russell is himself, immortalized as “Freddie”, the captain of the Queen Conch and the owner of Freddy’s Bar in Hemingway’s book “To Have and Have Not”.

  • Hemingway’s drink of choice was Teacher’s (a cheap scotch) and soda.

  • Hemingway loved the bar and he loved the urinal in the men’s room, a trough.  He always told his buddies that if anything ever happened to the place – he wanted the urinal and when Joe Russell and his patrons moved the bar to 201 Duval Street, the urinal ended up at Hemingway’s house on Whitehead Street.

  • Hemingway met his 3rd wife at Sloppy Joe’s.

  • Shortly thereafter, in mid 1938 Hemingway left Key West and moved to Cuba with her.

Information for Visiting Captain Tony’s Saloon

Address: 428 Greene Street, Key West, Florida

Phone: 305-294-1838

 

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About Marina Kuperman Villatoro

Marina Kuperman Villatoro CEO of TravelExperta.com, a travel resource site to inspire families to travel with kids of all ages. Marina has been an expat 10+ years in Central America raising 2 boys in a multicultural, trilingual household. She travels all over the world with her family to give first hand experiences of where to eat, stay and play with kids. Needless to say, it’s never boring! Join Marina on Facebook and Twitter for more unique and boutique family travel!

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