(gentle music) - [Narrator] The early pioneers who ventured to the Florida Keys encountered a breathtaking frontier, an aqua-tinted ocean brimming with conch and coral where endless flamingos filled the skies.

- [Resident] It's the light, it's the smell of the water.

- [Narrator] But the settlers also faced disastrous hurricanes and unforgiving reefs, where ships were wrecked by the dozens.

- [Historian] The pioneers, they were a sturdy lot.

You had to have something extra to come live in a place that was a wild outpost.

- [Narrator] The people who arrived on these shores would go on to change the Keys in many ways, but the Florida Keys would also profoundly change them.

- It felt exotic, it felt a little scary.

It's about a sense of inclusiveness that I didn't experience before in my life, and an openness and a feeling of you can be whatever you want to be here.

- I just want to leave the legacy that was handed me.

I want my grandchildren to be as proud of me as I am of my grandfather.

- [Narrator] These remote islands have seen dramatic, sometimes outrageous history over the last 200 years, with wreckers and Cuban cigar factories producing unimaginable wealth, where black Bahamians founded a proudly independent community.

- The African American history of the Keys and Key West is a story that is not out there, and it needs to be out there.

- [Narrator] An island chain where pirates, and later, Nazi submarines prowled just off the beaches, and where necessity really was the mother of invention as intrepid engineers constructed a railroad that soared high above the sea.

- There's ebbs and flows on this island that are almost innumerable, and Key West pivots like no other place, I think, on the planet pivots into what's next.

(energetic music) - [Narrator] Writers and musicians fell hard for this paradise.

Beautiful but quirky, different, offbeat.

- [Historian] We are so far from the real world that it is a chance to find those other parts within yourself.

(melodious music) - [Narrator] Today, visitors come for the world-class fishing, the tropical climate, and of course, the tempting key lime pie.

They come because the Keys know how to throw a good party.

(energetic music) - [Announcer] Happy Birthday, Key West.

(people cheering) - You can never enjoy getting lost somewhere like you can here.

- There's also people that come here to let their hair down, and I like to say, you either get it or you don't.

- [Narrator] But scratch the surface, and 200 years of adventure await with booms and busts, villains and heroins, war and peace.

It's this remarkable history that makes the Florida Keys one of the most fascinating places in our nation.

(horn trumpeting) (melodious music) - [Announcer] Major funding for this program was provided by... (melodious music) - [Advertiser] Where there is freedom, there is expression.

The Florida Keys and Key West.

- [Advertiser] Cultural, culinary secrets and global flavors.

We have a passion for blending ingredients and seasonings from around the world.

(melodious music) - [Narrator] On the 25th of March, in 1822, Lieutenant Commander Matthew C. Perry navigated the USS Shark to an island ominously known as Bone Key.

There, Perry planted the 23-star United States flag in the hard, limestone-riddled soil, and claimed land once owned by Spain, for America.

- Perry's job was to survey the island and report if it was feasible to make a Navy facility there.

- [Narrator] It was a strangely uninhabited island.

- Most of the Native Americans of Florida had left or died out from diseases, or been assimilated into what's now the Seminoles and the Miccosukees.

So, we know that by the time the Americans came to Keys, they had no record of any Native Americans being left here.

- [Narrator] A paradise full of peril.

- All the world's sailing through these waterways using outdated, incomplete charts.

As we well know, the reef runs several hundred miles and is at varying depths and varying locations, and it's pretty easy to get lost in it.

- [Narrator] Because so many ships got into trouble, sailors from the Bahamas, nicknamed Conchs, sailed up and down the Keys, working as wreckers.

- And wrecking was the job of going out and patrolling the reef-line, looking for ships in peril.

And your job as a wrecker was to approach the ship and offer your assistance in getting that ship safely off the reef.

Or if that wasn't possible, then to rescue the cargo and rescue the crew.

And for that, you were paid a percentage of the cargo.

- [Narrator] With so many ships wrecking, the government decided to take action, and by 1827, four brick lighthouses shone brightly through the night at Cape Florida, Sand Key, Key West, and in the Dry Tortugas, yet it wasn't enough.

- You got hundreds of miles worth of reef line that is not marked yet.

- [Narrator] Ships continued to run aground on the reef.

Word spread up and down the eastern seaboard that wrecking in the Keys was dangerous work, but it could make you rich.

- It was a major source of income.

- [Narrator] When New Englander, Karina Brown, arrived at Key West, she marveled that a wreck brought in last week was worth $140,000.

But, the Florida Keys could be tough on its settlers, it was a watery wild west.

- We'd been subject to piracy from particularly Cuban piracy at that time.

- [Narrator] To combat piracy, the West Indie Squadron was born in 1823, headed by Commodore David Porter of the U.S. Navy.

- The old anti-piracy squadron was using ships that were too big, couldn't get in and out of these narrow channels, couldn't get to the coast of Cuba.

So, Porter devised a strategy where he brought in shallow draft vessels, and barges, and really started making a dent against the pirates.

- [Narrator] But Porter had to fight more than just pirates.

- Now, Porter's problem was an enemy that they had not anticipated, and that was the Key West mosquitoes.

Porter's men were ravaged by yellow fever.

- [Narrator] One victim of the dreaded yellow fever was the head keeper of the Key West lighthouse, Michael Mabrity.

After his death, his wife Barbara, became the keeper, which was highly unusual at the time.

Climbing steep stairs each night in her long skirts, she kept the light shining, even through hurricanes.

Six miles away, on Tiny Sand Key, a fellow widow, Rebecca Flaherty, also kept a lighthouse, one of the few female keepers hired by the government.

- The women are very hands-on in building communities, they are also very active in their churches, and they are also physical builders, there's a lot of physical work to be done.

(melodious music) - [Narrator] On Key West, early leaders did their best to establish some sense of order, as it was an island with practically no law enforcement.

People seemed free to do as they pleased.

Men were even getting into deadly duels.

(gunshot echoing) (horse neighing) But this tropical frontier did not offer freedom to everyone.

- There's slavery happening, from the minute Key West gets settled, there are slaves on this island.

- Certainly, Key West wasn't, you know, this paradise of brotherly love.

I mean, we need to be real about that.

- [Narrator] Free people of color also faced harsh regulations and curfews and were eventually outlawed from moving to Florida.

In the 1850s, about 20% of Key West's Black population was free, including a free Black woman named Hannah Brooks, who had arrived from St. Augustine, a gifted nurse and midwife.

One settler recalled that she won the affection of all.

- Hannah Brooks delivered most of the babies on the island.

- [Narrator] Whites saw no contradiction in accepting medical care from a Black woman, and enslaving her sisters and her brothers.

Yet, despite all odds, the Black population persevered and created their own legacy.

(melodious music) You cannot underestimate the Black contribution to the Florida Keys.

- It's American history.

You know, it belongs to all of us.

You had Bahamians, you had from all over the Americas, you had even people from Cape Verde Islands.

And if you were emancipated, you had to been taught a skill, you know?

And that was British law.

The Bahamian emigrés that came to Key West were all skilled.

They helped build Key West.

- [Narrator] And in the 19th century, one free Black man literally kept Key West fed on an island where it was almost impossible to farm.

- There is no top soil, there's no alluvial soil, it's on limestone rock.

And no one since, has ever farmed anything to that magnitude on Key West.

- [Narrator] Sandy Cornish established a farm on land that belonged to his wife, Lilliah.

- At the time, women lawfully weren't allowed to own property.

But here, an African American woman owns two lots in Key West.

- [Narrator] Key West had long suffered from a shortage of fruits and vegetables, but Cornish was an innovator.

- So, he knew to mix the seaweed with the horse manure because there was no vegetation enough to collect to make compost.

What he grew on the farm?

All kind of tropical fruits like your sugar apples, your soursops, your guavas.

He grew grapes, melons, cabbages, sweet potatoes.

- [Narrator] Sandy Cornish had been born into slavery in Maryland.

By the time he was brought to Florida, he'd been in bondage for 40 years, at a time when the average life expectancy was only 35.

Just to enter Florida, the couple had to be sponsored by a white person.

- Lilliah, as a free Black person, was restricted from going into Florida.

So fundamentally, she had to put herself into slavery, where she never was, in order to be by his side.

So, they had to work off all this money and stuff like that, to buy their freedom.

- [Narrator] Freedom came at a high price, $3,000, equal to tens of thousands today.

Later, their freedom papers burned in a fire.

Seizing on that opportunity, a group of men tried to capture Sandy.

- So, they were gonna grab him and sell him in a market in New Orleans.

He takes a knife and cuts his hamstring right off, right?

Bam.

And he stumbles a little bit, he goes, "You still want this?"

And then, he cuts off his finger, puts it in his mouth like a cigar, and the crowd is shocked, obviously, you know?

So, basically, he's no good anymore.

Anything to be free, you know?

And that was the point.

- [Narrator] When Sandy was nearly 50, he and Lilliah started over, moving to Key West.

The nurse, Hannah Brooks, may have tended to his wounds.

Even as free people, the Cornishes still faced very restrictive laws.

Despite the discrimination, Sandy's fruit and vegetable trade was a huge success.

The Cornish Farm became a local institution.

- Though he's making money, he's making oodles of money.

- [Narrator] Sandy was now a leading citizen and helped to build a Black church.

- He's a very influential guy.

He's also African American, right?

Let's not forget that.

So, you have a mindset of people who basically didn't accept African Americans as people, in the beginning anyway, so he basically had changed a lot of people's mind because he had an astute knowledge of business.

- [Narrator] His success story appeared in newspapers across the nation.

- And his rise to iconic figure is now being set in motion.

(melodious trumpeting) - [Narrator] Although Florida would join the Confederacy during the Civil War, Union forces held Key West.

Black Key Westers served in the Union Army.

And then, after Abraham Lincoln was assassinated in 1865, President Andrew Johnson sent a group to the south to survey the effects of slavery.

The group traveled to Key West because word had spread about Sandy Cornish and this remarkable community.

- They say, in the report, that the most successful community, African American community in the South, was Key West.

So, they're arguing at this point to Andrew Johnson, saying, "No, African Americans are equal to white people because we have this community in Key West, you know?

That proves that if left alone, they could survive, they could prosper."

And that was the the major take-home message that they keep hammering to Andrew Johnson, to do the framework for reconstruction based on the community in Key West.

(melodious music) - [Narrator] Doors started to open for Black achievement.

- Key West elected not only a Black sheriff, Charles DuPont, but a Black county judge, James Dean.

- [Narrator] Famous abolitionist and writer, Frederick Douglas, even visited the island, and a school for Black children was established in his name.

The school opened in 1870, located in today's Bahama Village, a neighborhood with deep roots in Key West history.

(melodious music) While Sandy supplied Key West, throughout the Keys, both Blacks and whites learned to work the land.

- They farmed the land and they farmed the ocean.

- [Narrator] Pioneers grew key limes, and at one point, pineapples were very profitable.

- 85% of the pineapples consumed in the United States were produced in the Florida Keys.

- [Narrator] Until a blight destroyed the industry.

Despite Jim Crow laws that reversed the racial progress of reconstruction, Black settlers still saw opportunities in the Florida Keys.

- Georges and Olivia Adderley, they came from the Bahamas in about 1890, they moved to Key Vaca, better known as Marathon, and they bought- George bought 32 acres of land.

- [Narrator] George and Olivia built an unusual house of tabby, homemade concrete.

- [Brad] Today, their house, the Adderley house, is the oldest house in the Florida Keys that's outside of Key West, and it was built in the style of a classic Bahamian structure.

- [Narrator] The Adderley home became the cornerstone of an independent Black community.

- There was about five families living in what became known as Adderley Town, and they were farmers, fishermen, and sponges.

They made charcoal.

- The sponges really became part of this larger industry were largely people who had been enslaved and had been taken from Africa and released by the British government in The Bahamas when the slave trade became illegal.

- [Narrator] In the early 1900s, millionaire, Henry Flagler, wanted to build his railroad across George Adderley's land.

Adderley made Flagler strike a deal.

- He basically made the Flagler railroad stop at his property in Marathon.

- George was smart enough to know that if they had a train stop there, they could get their products, you know, to market better.

- [Narrator] There is so much Black history in the Keys still waiting to be discovered just beneath the surface, including one of the Florida Keys most famous wrecks, a slave ship named the Guerrero, that went down in 1827.

- When they were chased onto the reef, the ship sunk, so there were 561 of them on there.

41 of them died that night.

- [Narrator] Divers With a Purpose is working to find the site of the wreck where so many Africans lost their lives.

A 16 year project.

One theory is that the ship sank north of Key Largo, in today's Biscayne National Park.

- We were promised that if and when it was found, that we as African Americans would be the first ones to be able to document that wreck.

And for a lot of people, it was about being where the ancestors lay and just being a part of history.

We need to know what happened to these folks and put this thing to rest.

A lot of African Americans don't wanna talk about slavery, but you have to know your history, you have to know where you've been so you can know where you're going.

- [Narrator] To fully understand the Florida Keys story, you also have to turn to the history of Cubans and Jews.

(melodious music) In the late 1860s, a New York tobacco trader set his sights on Key West.

Samuel Seidenberg saw big opportunity in the tiny distance between Key West and Cuba, then the cigar capital of the world.

A few years later, another tobacco man came to town, this one from Cuba, Eduardo Hidalgo Gato.

On the surface, the men had little in common other than their line of work.

Seidenberg was German, Gato, a Cuban of Spanish heritage.

Seidenberg was Jewish, Gato, a Roman Catholic.

The two entrepreneurs represented two very different communities that would transform Key West like a tremendous tide.

- The Jewish community in Key West had a huge impact on what we think of as Key West today, what we think of as Key West history.

- Key West had the first Cuban American community in the United States.

- [Narrator] Despite their differences, Key West Jews and Cubans had something in common.

They were both people living in exile, united in their hunger for freedom.

- The Cubans saw in Key West the place where they could come to plan the struggle for Cuba's independence.

- Jewish immigrants had left their homes in Europe due to persecution.

- [Narrator] Before the 1870s, only a modest number of Cubans and Jews made their home in the Florida Keys.

Yet, Key West began to earn a reputation for tolerance.

- It was a multicultural place, it was a multilingual place.

Close to 50% of people living in Key West around the 1890s were either Cuban-born or had at least one Cuban parent.

It was a town, you know, of immigrants.

So, Jews that were coming to Key West were coming to a place that didn't really look like a lot of America.

(melodious music) - [Narrator] But while those immigrants might possibly find a haven, jobs were another story.

With the wrecking business in decline, Key West no longer had a profitable industry.

Local shops produced small batches of cigars.

But for decades, Cuba had dominated the luxury cigar industry.

All that would change.

- [Historian] People continued to be enchanted by cigars, and it's always told as a Cuban story.

- But more recently, researchers have uncovered that Jewish entrepreneurs also played a pivotal role.

- [Historian] Samuel Seidenberg capitalized on a tariff structure that had gone into place in the 1860s, that made it financially advantageous to produce cigars domestically in the United States.

So he moved to Key West, established a huge manufacturing base here.

- [Narrator] Meanwhile, the bloody Ten Years' war erupted in Cuba, an effort to overthrow Spanish rule once and for all.

Rebel sympathizers, like Eduardo Gato, relocated their cigar businesses to the closest American port city, Key West.

- The Cubans who came were from all walks of life, they were rich and poor, and even the women worked in the tobacco factories here.

- They could maintain a very close connection to the homeland.

Remember, Key West of the time was not connected to Florida's mainland.

- [Narrator] While in the rest of the Florida Keys, people made their living by farming and fishing, Key West became the nation's chief producer of cigars, using Cuban tobacco leaves.

- [Historian] The cigar-making industry really was the economic engine, starting in the 1860s and then running through the 1890s.

- [Narrator] Cigar money flooded the island.

Samuel Seidenberg made a fortune worth 9 million in today's dollars.

Eduardo Gato built himself a mansion on Duval Street.

He created the island's first street car line and built 40 cottages to house his workers.

A neighborhood they called Gatoville.

But the cigar industry wasn't the only thing imported from Cuba, there were also revolutionary politics and a revolutionary leader.

- The period of the 1880s and the 1890s when José Marti was here, organizing the Cuban Rebels.

- [Narrator] José Marti was a famous activist and poet who wrote verses that were turned into beloved songs, verses still sung by Cubans today.

♪ Guantanamera ♪ ♪ Guajira Guantanamera ♪ Both Gato and Seidenberg invited Marti to speak at their cigar factories.

- In Marti, they recognized a leader who was fighting not just for Cubans, as Marti said, but for the rights of all people.

He identified the sense of Cuban exile, which he hoped would be temporary, with this longer deep historic sense of Jewish exile.

- [Narrator] Jews like Louis Fine lent their support and contributed money, and they participated in smuggling operations that delivered arms to the rebels.

- Louis Fine, he was not an ordained rabbi, but he was the defacto rabbi for the community.

He was the religious leader.

It was his family that told the story about collaboration with the Cuban revolutionary fighters under José Marti.

And I thought, you know, that's probably my great-grandfather was friends with George Washington kind of story, and I didn't buy it initially.

That particular story is a great example of something that not only turned out to be true, but turned out to be a much bigger story than the family knew.

(rhythmic drumbeat music) - [Narrator] On Duval Street, factory owner, Teodoro Pérez, introduced José Marti from the balcony of his own house, a place that would come to be known as La Terraza de Marti.

Marti's Balcony.

José Marti later wrote in a letter, "I can't deliver from my heart as I wanted to, all the tenderness, the just pride, the gratefulness that in the name of our country, we all owe to the Cuban immigrants of Key West."

- Key West has always been a symbol of freedom and hope for the Cuban people.

- [Narrator] Spain did not look kindly on Key West's support of the Cuban rebels.

In one instance, a Spanish newspaper editor challenged a pro-independence Key West journalist to a duel.

And when the great fire reduced much of Key West to ashes in 1886, rumors flew that Spanish agents were to blame.

(trumpeting music) In 1898, the United States joined the fray.

Soon, Teddy Roosevelt's Rough Riders were sailing over to Cuba for the 10-week-long Spanish American war.

Spain signed a treaty, and by 1902, Cuba was truly free.

Cubans in Key West rejoiced at this victory.

At the same time, Key West fortunes were beginning to crash.

- The cigar-making industry was largely moving to Tampa.

- It was easier to transport the finished cigar from Tampa than from Key West.

- It was the kind of downfall of the cigar-making industry that started to push Key West into a depression, into an economic downturn.

You talk about, you know, the roaring twenties, but the 1920s in Key West were really, really hard times.

- [Narrator] Yet, the story of the Cubans and the Jews doesn't end with the death of Key West's cigar industry.

- [Historian] The economic difficulties of 1920s Key West coincided with a period of real anti-immigration hysteria, antisemitic hysteria.

- [Narrator] In Germany, something called the Nazi Party was gaining support.

And here at home, in idealistic Key West, the Ku Klux Klan was on the rise.

At the same time, the U.S. government drastically cut immigration from the very countries that Jews were hoping to escape.

- [Historian] Because of various legal loopholes, they would often go to Cuba and then try to come from Cuba into the United States.

- A new kind of smuggling exploded.

This time, it wasn't weapons, it was people.

- Those smuggling routes were kind of reopened in the service of, you know, bringing Jews to safety in the United States.

And the community here, had access to a series of underground kind of chambers and even a tunnel system that connected some of them in Old Town Key West.

- [Narrator] Both Cuban and Jewish smugglers ferried Jewish refugees across the Florida straits.

They landed not only at Key West, but also on Summerland Key, Long Key, Marathon, and Big Pine.

- There was the smugglers who were sort of following the Higher God's law.

There were also a lot of smugglers who were just doing it to make a buck at that time.

- [Narrator] Once again, Key West served as a sanctuary.

Some of the smuggled Jewish refugees traveled north to reunite with family members, making the journey often not by boat, but by train.

Because now, linking the Florida Keys to the American mainland was an engineering marvel, the overseas railroad.

In 1902, an engineer set out from Miami with a crew of men.

Their goal?

They were looking to do the impossible, build a railroad to Key West.

- Initially, the only way to get down to the Keys, especially in the 19th century, was by boat only.

There was no road to connect the Keys to the mainland at all.

- [Narrator] William Krome had been hired by standard oil millionaire, Henry Flagler, to help him fulfill a dream.

- He decided that the State of Florida was an undeveloped frontier where he could build a chain of hotels and make Florida the Riviera of the United States.

- [Narrator] Krome reported to Flagler that building a railroad to Key West through the Everglades would never work, better to take it through Key Largo.

- I don't know that the federal government could have afforded to build the bridges in the Keys at that time.

There would be question as to whether or not we would be here today if it wasn't for Henry Flagler.

- Well, some people called it Flagler's Folly.

The railroad never made money.

Other people called it one of the greatest engineering feats of American history.

You're having to create 42 bridges over 17 miles of open water.

And of course, in those days, that was an extraordinary accomplishment.

- [Narrator] Construction on the railroad began in 1905, and after all his hard work serving for Flagler, Krome thought he deserved the top job, Chief Engineer, but the boss hired someone else.

Even before reaching Key Largo, engineers discovered a large body of water where they expected to find land.

They named it Lake Surprise.

A surprise that added another 15 months to their schedule.

(cheerful music) Flagler employed around 4,000 workers who were often inventing equipment to help them push through mangrove swamps and coral rock and build across waterways.

The company installed a headquarters in the Middle Keys called Camp Number 10, in what is now known as Marathon.

Flagler had forbidden alcohol at the work camps, so a ship named Senator opened as a bar and a brothel.

By 1908, the track extended from Miami to Knights Key dock in Marathon.

Here, Flagler's steam ships could meet passengers and whisk them away to Key West and Cuba.

Tourism remained at the forefront of Flagler's plans.

- Henry Flagler connected not only the Keys to the mainland, but he developed resorts up and down the Keys.

- [Narrator] But in 1907, there was a problem.

Flagler had been dredging material from the ocean floor to create land for the final station at Key West, but the Navy swiftly put a stop to this.

Flagler ordered all work south of Knights Key stopped.

(melodious music) The company laid off workers.

It was a nerve-wracking time.

Krome, tired of playing second fiddle, quit.

For nearly two years, Key West and Flagler's crew waited to see if they would get a connection to the rest of America.

President Theodore Roosevelt hadn't wanted to overrule the Navy.

- It finally ended, just all of a sudden.

- [Narrator] Flagler won the standoff.

South of Marathon, engineers and workers had the massive task of building four bridges across seven miles of ocean to take the line the rest of the way to Key West.

That same year, the chief engineer on the project died.

The company begged Krome to return, and he did, so that an ailing Flagler could see the project completed.

(bright music) - On January 22nd, 1912, Henry Flagler got aboard his private car, the Rambler, and came down to Key West.

- That's what they opened in, in 1912.

It wasn't really complete now.

- [Narrator] The first passengers rode across the many bridges in amazement, nothing on either side of the tracks but miles of sea.

Krome had made sure that his 82 year old boss made it to Key West.

"Now, I can die happy," Flagler said.

Finally, the Keys were connected to the mainland.

The railroad brought immediate changes.

- Mail arrived every day, eight o'clock, it brought this consistency.

And a lot of the communities began to move away from the edges of the island and closer to the railroads.

Tavernier is a perfect example of this.

You didn't have to worry so much and life wasn't such a struggle.

- [Narrator] Tourism did not take off as Flagler had hoped, but one local lifelong Key West resident remembers stowing away in one of the train's box cars.

- So, about nine o'clock, a little friend group of us, we used to sit in the corner of Duval Street, and then all of a sudden, this guy come, he say, "Tonight is a big train going north and full of pineapple that he had come from Cuba."

We look at each other, "Let's go to Miami."

(cheerful music) - [Narrator] The band of friends did get caught, but only once.

- They got me off in Marathon, and we all had to get off.

So we say, "How're we gonna get back to Key West now?"

(cars rumbling) - [Narrator] In the 1920s, Americans were falling in love with cars.

To encourage people to drive from Miami to the Keys, work began on Card Sound Road.

By 1928, you could drive to Key Largo.

If people wanted to go further though, they had to take a ferry.

- The road would stop, you'd hop on a ferry with your car, continue on, and then get back on a road and go.

- [Narrator] To avoid the ferries, people could drive on railroad bridges, even if that wasn't strictly allowed.

One company even enticed people to do just this.

- [Advertiser] Out to sea in an automobile, on a road through the Atlantic Ocean.

- And what Chevrolet was hoping to achieve was saying their ride was so comfortable that you could forget using the ferry, you can actually just drive over the train tracks instead, and you wouldn't feel any of the bumps because it was such a smooth ride, so you can forego the unfortunate ferry ride.

- [Narrator] But the most famous couple to reach Key West in that era, did not arrive from the American mainland.

Ernest Hemingway was traveling from Cuba with his second wife, Pauline Pfeiffer, an accomplished journalist in her own right.

While the two met in Paris, the island where they now found themselves could not have been more different.

It was rough around the edges.

It was Prohibition time, a hub for rum-runners like the notorious Spanish Marie.

Hemingway was in on the action, he too smuggled liquor from Cuba and frequented the speakeasy owned by his friend, Joe Russell.

After prohibition ended, Hemingway suggested Russell call his bar Sloppy Joe's and became one of its best customers.

The men treated drinking like a mission.

By 1931, Pauline's rich uncle had bought the couple a mansion on Whitehead Street.

Hemingway developed a routine of writing, drinking, and fishing, usually on his beloved boat, the 38 foot Pilar.

Then came Labor Day, 1935, the end of summer, humid and quiet.

In the Upper Keys, visitors at the Caribbee Colony sipped cocktails.

In Key West, Hemingway hurried to secure the Pilar.

As night fell, all of the Keys, especially Islamorada and Key Largo, hunkered down for a hurricane.

The keepers at the Alligator Reef Lighthouse watched the seas below in horror, as a wall of water swept towards land.

- People clinging to lime trees, which have, you know, big, long thorns in them.

They're just clinging to thorns to survive.

- [Narrator] Bodies were everywhere.

The entire Caribbee Colony resort and all its guests vanished.

- At that time, the railroad was being converted to the overseas highway and there were several hundred World War I veterans working on it.

And the supervisor of that did not take the hurricane seriously at all and did not provide an evacuation plan until it was too late.

Hemingway arrived shortly after the hurricane and he toured the devastation.

- 200+ veterans were lost to that hurricane, and as a World War I veteran himself, he came up here and really took offense to the way things were being handled.

You know, there were delays in getting medical attention for those who did survive, and ultimately, they couldn't get personnel in here quick enough to move people out in body bags and caskets.

- He wrote this scathing essay and he lobbied Congress.

- [Narrator] The writer's passionate words drew national attention to the hurricane's devastation, the Upper Keys buried their dead and slowly rebuilt.

(melodious music) The overseas highway was finally completed and all the Keys were easier to reach.

Henry Flagler's railroad tracks and bridges had been converted into the bed of the highway.

After World War II, which saw a huge Navy presence and Nazi submarines lurking offshore, sports fishing became a big draw.

Even President Harry Truman and his wife, Bess, would cast their lines.

- We were always blessed to have a lot of bonefish, and I mean a lot of bonefish.

In no small degree, a great population of tarpon as well.

I always mention Ted Williams because in no small way, he put Islamorada on the map when he started coming down here in the early fifties.

He was as big a name as there was in sports, and he is also an incredible bone fisher and tarpon fisher.

(melodious music) - [Narrator] And while most boat captains in the Florida Keys were men, women started earning their captains' licenses too.

Captain Bonnie Smith and Captain Frankie Albright gained excellent reputations as fishing guides, as did their sister, Beulah.

Over time, the three Laidlaw Sisters became local legends.

(melodious music) By the 1950s, the Upper and Middle Keys experienced a true tourist boom, and it wasn't just fishing that attracted people.

(water sloshing) - There are more than 2,000 shipwrecks that we know of in Florida Keys' waters, because of the way our reef is set up around these islands.

(melodious music) Art McKee, we consider him really the father of modern treasure diving, as well as one of the first purveyors of recreational diving, here in the Keys.

(melodious music) He definitely sparked other people's interest in diving treasure.

Not a lot of people were doing it at that time because it was so cumbersome to use standard diving equipment.

But with the open bottom helmets, there started to be more interest in diving, so much so that by the 1950s, Florida had to actually enact new legislation because there was this craze of treasure diving all throughout Florida.

- [Narrator] Another treasure hunter, Mel Fisher, then discovered an even bigger haul.

The Spanish galleon, Atocha, with gold, silver, and emeralds, worth many millions of dollars.

(tense music) Even without Spanish treasure, the Florida Reef with its spectacular tropical fish was becoming an attraction.

- The reefs in Florida are the only coral barrier reefs we have in North America.

They're the only ones we have.

(mystical music) They're important because they provide coastal protection to those of us that live on these low-lying islands.

The 1980s were a difficult decade in the Florida Keys, from the ecosystem perspective.

We started seeing signs that there was trouble.

Establishing Florida Keys' National Marine Sanctuary really set the mark that this is a national treasure, this is a special place, and provided a whole host of protections for these natural resources.

- [Narrator] But there is still work to be done.

Fangman recalls an interview that stuck with her.

- I was behind the camera while a 16 year old, relatively new diver, was being interviewed.

She'd been diving for two years.

She was interviewed and asked, "Tell us about your experience diving these reefs."

And she proceeded to describe how she had watched the reefs decline.

Two years, 16 years old, we need to do better than that.

And my goal, my hope, is that when she's my age, she is instead bearing witness to this thing turning around, how we've recovered these reefs.

(melodious music) - [Narrator] On Big Pine Key, the National Key Deer Refuge protects the unique tiny deer only found on that island.

And organizations like Captains for Clean Water are trying to ensure that the next generation, like Hemingway, can still fish here.

(melodious music) - [Historian] I think the remoteness of it attracted many writers, and it was a way that they could really get away from the world that they normally lived in.

- [Narrator] There were many who followed in the footsteps of Hemingway.

- He consciously tried to apply the rules of journalism to the principles of fiction.

You know, short words, short sentences, short paragraphs, declarative sentences.

- The way he is able to create a moment in a scene without giving too much interior.

- You know, Hemingway famously said that a story should be like an iceberg.

90% of it is underwater and out of sight.

- I think all of that has been a part of his influence on my writing.

He's talking from a certain time, a certain period, which is not to say I accept that as as a modern writer, or as a teacher, or as a woman, but that I take note of it.

So, I think that in terms of Hemingway and his misogynistic perspective, he's a marker of time.

And when we read him now, we get to see what progress, if any, there has been in literature, what progress there has been in the way we portray women or people of color.

(energetic music) - [Narrator] More writers arrived in the 1930s.

- [Historian] Elizabeth Bishop was one of our most important 20th century poets.

- [Narrator] Bishop, who would later win the Pulitzer Prize, was just 25 when she first visited.

The New Englander found Key West exotic.

"The town is paper-white," she wrote.

"flake on flake of wood, and paint the buildings faint."

In the depression, Real estate was cheap.

She bought a house and moved there with her partner, Louise Crane.

She knew Pauline Hemingway, now divorced.

The women went out to Sloppy Joe's, where they danced the rumba in satin dresses.

Another of Bishop's friends was the playwright, Tennessee Williams.

A young musician was also writing the Keys' very own soundtrack.

- I mean, the greatest thing ever written about Key West is Jimmy Buffett's song, "Margaritaville".

That's the "Getting lost in Key West" song.

- Jimmy was definitely a part of this time.

He came down and he started playing, and we'd hear him around town.

He was our local celebrity.

He was part of that old Key West.

- [Narrator] Key West was a muse for a much-loved children's book author too.

- Shel, Shel Silverstein.

He was another one that you would see just everywhere you go.

- "There is a place where the sidewalk ends and before the street begins, and there the grass grows soft and wide, and there the sun burns crimson bright."

And I think, "God, that sounds like Key West."

(melodious music) I think it's fascinating to have this new cohort of women writers down here.

Judy Blume, and Annie Dillard, and Anne Bede.

After, you know, the legacy in the seventies of the guys chasing Hemingway's ghost, Hunter S. Thompson, Tom McQuain.

- But I think it's really interesting that the way Key West works now.

It seems to me that it's also this place for readers and wanna-be readers to go and pay homage to some of the literary history that's there.

- [Narrator] Today, many of the writer's houses are lovingly cared for.

This wasn't always the case.

(melodious music) After the boom years of World War II, the city of Key West slid into a slow economic decline.

The other Keys were drawing in tourists with fishing, and diving, and roadside attractions.

Even the dolphin who starred in Flipper.

But in Key West, the party was over.

- The Navy was was pulling out at that point.

- I'd moved down in '75.

This town was shut down.

- [Narrator] Key West was an island in need of resuscitation.

One community decided to give it a chance.

- In the 1970s, we had a big influence of gay business owners moving down here and opening businesses, and buying up all the property and fixing it up.

- [Narrator] And in the 1970s, there were few places in America where gay men and women could live openly without fear.

Key West wasn't perfect.

One night, a group attacked famed writer, Tennessee Williams, yet the sense of greater acceptance was real.

- I was a very terrified young gay man.

I wasn't out to myself.

I came when it had already...

There was a certain sense of acceptance.

(cheerful music) - [Narrator] As Key West started to pull out of its financial slump, concerned residents saw another urgent problem.

The island's precious architectural heritage was under threat.

Paint was peeling off the grand Victorian mansions, cigar makers' cottages were crumbling.

- We had a lot of the gay writers come in and they put their money in these buildings.

- [Narrator] The city got a much needed facelift.

- About 1976, '77, a group of concerned businessmen and the city commission at the time decided that they wanted to revitalize Duval Street and Bahama Village itself.

It was also an effort to tie us in more closely to our Bahamian roots.

- [Narrator] The rich and famous began to take notice of the island's revival.

- Then also, actually, Calvin Klein came down, and the reason why he loved Key West is because no one bothered him.

It was such a small-type community.

It was a magic time.

- [Narrator] That magic revived Key West nightlife.

Before long, they took the party to the streets.

- That initial Fantasy Fest, this kind of really inspired a parade that people just put together with small floats and costumes, and everyone was out on the streets watching it.

But this was not an international, this was a local thing.

- There were six women coming down the street, they were wearing top hats, red shorts, little, tiny, red, glittery shorts, they had a cane and tap shoes, and they were tapping their way down the street, topless.

And probably, the youngest in the group might have been 60.

They had the routine down and everyone just loved them, applauded them.

- [Narrator] That local celebration turned into a yearly tropical festival to rival New Orleans' Mardi Gras, or Rio's Carnival.

Optimism flowed through Key West like a welcome breeze.

The island elected one of the country's first openly-gay mayors, Richard Haman.

But in the early eighties, the good times faltered.

Its most beloved gay resident, Tennessee Williams, died, and Key West faced a sobering new reality.

The AIDS crisis.

Eventually, this led to an AIDS memorial and the first Key West Pride parade.

While the gay community could unite openly on the streets, over in Cuba, people were thirsting for freedom.

(melodious music) - And then, in that time, the Mariel boat lift started, and we were just getting to the point where our tourist industry was coming back to life.

(melodious music) - [Narrator] Dictator, Fidel Castro, was allowing Cubans to escape from the Port of Mariel.

Boats left South Florida to bring back family members and other refugees.

(bright music) At this time, tourism had been picking up, plans were afoot to modernize the overseas highway with a new and improved seven mile bridge.

Then in 1982, tourist traffic came to a halt.

- Nobody can get out of the Keys.

They're backed up all the way into Key Largo.

It's a 23 mile traffic jam.

I called the police chief, he said, "I haven't heard anything."

- This was during the war on drugs.

So, the government decided to erect a... Basically, a border checkpoint at the top of the Florida Keys.

- So, I called the office and got Congressman Fissel on the phone, and I asked him, I said, "What is going on?"

I said, "We are getting killed here.

People are canceling reservations."

- That border checkpoint created one of the largest parking lots ever seen.

Everybody who's being stopped is being asked to show their identification as if they were leaving a foreign country.

- My phone's ringing off the hook, people want to know what's going on.

Why can't they get outta here?

And I'd like to know, you know, why you all are putting this up?

- They want to look for drugs, but they're saying that they're looking for illegal aliens.

Of course, this becomes a international story, and it's great to come to visit the Keys, but once you get here, you can't get out.

So, the Mayor of Key West, Dennis Wardlow, they come up with a great plan.

- And I said, "Tomorrow at noon, we're going to secede and become the concrete public.

If they're gonna treat us as a foreign country, we're gonna become a foreign country."

(people cheering) (melodious music) - [Narrator] Mayor Wardlow ordered the American flag to be lowered at Key West.

As part of the gag, the New Republic declared war on the United States by hitting a military serviceman over the head with a baton of Cuban bread.

- And right after that, within a minute, I surrendered, and I think then I asked for a million dollars in foreign aid.

We raised our flag and then, you know, everybody, like everything else, we start celebrating.

(energetic music) - [Narrator] The Florida Keys adopted the Conch Republic flag as a quirky badge of honor.

Later, when Monroe County Mayor, Wilhelmina Harvey, met the Queen of England, she presented the Queen with a conch shell.

(melodious music) The 1990s ushered in an era of growth and prosperity.

Some travelers took the scenic route, vacationing in the city of Marathon or on the quiet island of Sugarloaf.

On Key West, visitors lined up to see the legendary drag shows.

The house known as La Terraza de Marti, where Cuban revolutionary, José Marti, once gave a stirring speech, was now called La Te Da, a cabaret where drag stars sparkle in sequins.

- I mean, I have all ages at my show, in every walk of life.

I've had a priest, a nun, a rabbi, multiples.

They all come, they have a great time.

I try not to offend too much.

- Do you believe?

(crowd cheering) - [Narrator] As the new millennium dawned, Key West celebrated gay pride with a flag the length of Duval Street, one and a quarter miles long.

In 2015, the island saw its first same-sex wedding.

And in 2018, Key West elected Terry Johnston, Florida's first openly-lesbian mayor.

(energetic music) - Come, be who you are, we'll be who we are.

(energetic music) - [Narrator] For two centuries, the adventures have unspooled like colorful threads, sewing together stories of wreckers and writers, rum-runners and refugees.

- It's unlike any place else you've ever been.

It's that simple.

(mystical music) - [Narrator] After 200 years, the pull of the Florida Keys continues like a current in the sea.

A home for exhibitions, parades, contests of all kinds.

A literary seminar that attracts thousands.

The sheer beauty of the land continues to inspire books, television, and movies.

- The scenery is so amazing and it's filmed all, you know, right here.

It's amazing to sit there and watch your home, you know, on screen.

(melodious music) - [Narrator] It is an escape to the very edges of our nation.

- You're far enough away that you're at a distance, and yet, you're still in it, you know?

So, you get this interesting sense of context on the country.

(melodious music) - [Narrator] A place where history is part of the landscape, an ongoing tale of restoration and renewal, the railroad's old seven mile bridge, brought back to life, new generations at the church built by Sandy Cornish, and the hope it represents.

(water gurgling) At the center of everything, is nature in a starring role, as people try to ensure the future of the ocean, the fish, the turtles, and the coral reefs.

The Florida Keys will always be a place for simple pleasures, key lime pie, the perfect cup of Cuban coffee.

(melodious music) And each night, people gather by the shore to watch the sun like ribbons of gold as it dips below the horizon.

A moment of shared happiness, uniting them all, from Key Largo to Sugarloaf, Marathon to Mallory Square.

- It's hard to tell a Key West story, it's hard to tell an Islamorada story, or a Key Largo, or a Marathon story.

This is one long and one giant community.

The writer in me likes to, you know, weave these stories to tell a bigger story that really are Florida Keys' stories.

(melodious music) - [Announcer] Major funding for this program was provided by... (melodious music) - [Advertiser] Where there is freedom, there is expression.

The Florida Keys and Key West.

- [Advertiser] Cultural, culinary secrets and global flavors.

We have a passion for blending ingredients and seasonings from around the world.

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