Hemingway Tour Key West – Legendary Resident

The Ernest Hemingway Key West Home Years

 During the Hemingway years (1929-1939), Key West was in a desperate condition.

In the 1830s, Key West was the richest city in the country. The next hundred years were not kind.

The Civil War brought political division. The largest cigar-making industry in the world moved to Tampa. The sponge docks were moved to Tarpon Springs.

The Great Depression left people homeless and penniless. Prohibition shut down alcohol importation, and finally, Key West went broke. 

The state and federal governments implemented work programs to give people income. They cleaned up Key West and started to advertise it as a tropical getaway.

Ernest Hemingway Tour Key West Home – Model of Extravagance in the 30’s

Amid all the unfortunate circumstances in Key West, Hemingway and his second wife Pauline moved to Key West in 1929. 

After a brief visit in 1928, they wanted to come back. Hemingway loved the remote tropical feel of the island.

At the time, there were no roads to bring throngs of visitors. People were poor, but Hemingway married into a rich family and could fuel his need for privacy to write.

His fame was limited at the time. His notoriety primarily came from articles written in Paris.

The result was Hemingway fell in love with the island and its people. Subsequently, his ten-year relationship with Key West was longer than some of his four marriages.

The Ernest Hemingway Tour Key West of his home is one of the top 3 attractions in Key West today.

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Ernest Hemingway’s Key West Still Partially Alive Today

After discovering Key West on the recommendation of a fellow writer in Paris, Hemingway spent most winters on the island paradise for a decade.

Pauline’s family bought them the house at 907 Whitehead Street. With Pauline’s skill and money, they created a home for their three children and a haven for the writer to pursue some of the best books and short stories of his career.

Hemingway’s Key West was “St. Tropez of the poor” as he wrote to another friend.

While a prolific writer, Hemingway was just as resolute with his fishing, boating and drinking. Unknowingly, he created what was called locally the “Mob”.

These were friends that hung with the worldly sportsman that Hemingway became. He had a collection of charter captains, fishermen, bar buddies, boxers, foreign-based writers, and his most famous local compadre, “Josie” Russell.

Josie is better known as the owner of Sloppy Joe’s where the “Mob” hung out.

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Hemingway’s Bars in Key West

Joe “Josie” Russell ran a speakeasy during prohibition at 428 Green Street.

Today that address is Captain Tony’s. This location was the first bar owned by Josie Russell and he named it Sloppy Joe’s after prohibition ended in 1933.

Then in 1937, Josie and customers moved the bar a block away. Overnight, as a result of a dollar-a-week rent increase, friends picked everything up and moved.

For a few drinks, Sloppy Joe’s was relocated to its current location at 201 Duval Street.

One of the events that soured his relationship with government officials was the 1935 record hurricane that killed 400 WWI veterans w

orking on Flagler’s East Coast railroad. Hemingway felt the veterans should have had a way out of the Keys. 

He ranted that the government should have provided an escape before the estimated 250-mile-per-hour winds caused death and havoc.

Hemingway and His Travels

Many accounts of Hemingway’s days in Key West forget he was frequently traveling. He loved Wyoming and the big game available.

Cuba was a frequent stop for fishing and partying adventures. Bimini was a favorite for marlin and tuna. In 1933 Hemingway and Pauline traveled to Africa for 10 weeks.

Spain was a destination he loved as he developed an interest in bullfighting which lead to his book Death in the Afternoon.

By 1939 Hemingway was about to depart Key West for good. It was clear that war was brewing in Europe and his experience in WWI led him to become a war correspondent in WWII.

A year earlier, the Overseas Highway was completed to Key West, bringing more tourists and the notoriety Hemingway tried to avoid.

He only visited Key West a couple of times after that, but the family retained ownership of the Ernest Hemingway Key West Home property his home on Whitehead Street until his death in 1961. 

Hemingway’s Key West is not the same as today’s Key West. Is it better?

Hemingway wouldn’t think so! Take a Hemingway tour in Key West and you be the judge.