Anna Maria Island’s Colorful Past: Wilderness to Modern Paradise

The peaceful façade of Anna Maria conceals the history of a movie star captured by cannibals and a pirate stranded on a deserted island.

The cannibals were fakes, created by Hollywood for the 1948 movie, “On an Island with You,” filmed in Anna Maria’s tropical paradise.

However, a real pirate, Jean LaFitte, was shipwrecked near Anna Maria in 1821, and nearly a century later, Fig Newton cookies paved the way for the island’s first streets and sidewalks. (More about that later.)

Then a decade or so after the island acquired its first streets, a tavern opened where the Sandbar Restaurant is now located, and barroom brawls made a debut.

So authorities concocted sobering punishment for rowdy drunks. The island’s first jail cell was built in 1927. Inmates were held in the outdoor cell while thousands of mosquitoes feasted on them all night. The cell’s windows had bars but no glass or screens.

Mosquito torture was inflicted on prisoners for more than a decade until a fire destroyed parts of the cell in the 1940s. The jail remains on the island without a roof or a door, and it is unique enough to merit mention in Ripley’s Believe It or Not.

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Also in the 1940s, the island airport set the stage for a Hollywood movie. Suddenly hundreds of Metro-Goldwyn-Mayer workers descended on tranquil Anna Maria.

Jack Holmes had cleared 30 acres of jungle on his 350 acres in Holmes Beach for the airport in 1947. The “airport” was actually a landing strip constructed in 13 days. Before it was finished, MGM contacted Holmes with the Hollywood proposal.

So, Anna Maria masqueraded as a deserted south sea island for the movie, “On an Island with You.”

As fantasy unfolded, Hollywood’s swimming star Esther Williams led elaborate water ballet sequences, and supporting actress Cyd Charisse danced rumba while an orchestra played on the remote island.

Meanwhile, Williams was kidnapped and cannibals captured Ricardo Montalban. Williams was engaged to Montalban but she fell in love with Peter Lawford. However, it ended well because Montalban and Charisse also fell in love with each other.

Today city offices, a library, fire station, and recreational facilities cover the “airport” that brought danger and romance to Holmes Beach.

Just Human Bones, No Buried Treasure

Let’s go way back to the beginning. The island was formed about 25,000 years ago, according to data from the Anna Maria Island Historical Society.

Humans started inhabiting Florida about 12,000 years ago. Meanwhile, the barrier islands created a bountiful ecosystem that attracted settlers, the predecessors of the Calusa Indians, about 4000 years ago.

Fast forward over the millennium to the 1530s. Explorers claimed Anna Maria for Spain, and they encountered powerful Indians covered with tattoos. The Tocobagans were one of four tribes using the island as a base for fishing, foraging, and hunting turtles, according to Bill Burger, local historian and anthropologist.

Spanish rule in the area ended when the U.S. acquired Florida in 1819. During that century there were several tales of ships wrecked around Anna Maria.

The shipwrecked pirate LaFitte left his mark on an Anna Maria preserve, Leffis Key on the bayside south of the island. Some speculate that the original name was LaFitte’s Key.

However, no buried treasure was ever found on the island; instead human bones were discovered. The bones and brass buttons were unearthed by the first homesteader when he was digging wells, according to the Anna Maria Island Historical Society’s “The Early Days 1893-1940.”

The first homesteader, George Emerson Bean, asked the U.S. War Department about the origin of his find. He was informed that all those aboard a federal fleet had drowned at the North Point of the island in 1864 during the U.S. Civil War, according to the historical society’s book.

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Bean became a homesteader in 1893 when the island was a harsh paradise infested with mosquitoes and animals, including rattlesnakes, alligators, and porcupines. Supplies, mail, and news arrived only by boat, according to information at the Anna Maria Island Historical Museum.

Early homesteaders raised chickens, planted vegetables and fruit trees, and there were plenty of fish in the sea.

The mullet were jumping, and the sea was thick with redfish, trout, bluefish, Spanish mackerel, and pompano. In fact, the Gulf still has one of the world’s most bounteous marine lives, according to Jack E. Davis, author of “The Gulf, the Making of an American Sea.”

Due to that bounty, early settlers never went hungry. In the nearby Village of Cortez, residents even referred to the Gulf as “the kitchen,” according to Davis.

Cortez, still a working fishing village, one of the last in Florida, was founded in 1890 by families from North Carolina. Cortez provided the link to Anna Maria from the peninsula of Sarasota Bay.

A boat from Cortez was the final part of a journey to Anna Maria for Tampa residents seeking recreation on the island. To arrive in Cortez, they would first take a barge at the Alafia River.

Long Dresses in Wilderness, Million Dollar Cookies

Fishermen as well as hunters and campers visited the island in the 1800s even before there were homesteaders.

A photo in the island’s history museum shows a boatload of vacationers returning from Anna Maria. In it the women leaving the wilderness are wearing floor-length dresses. According to museum attendants, the picture is probably from Bean’s era.

Bean homesteaded a large tract of land from the North Point to Magnolia Avenue. Bean Point on the island carries his name.

His son, George Wilhelm Bean, and his associates formed the Anna Maria Beach Development Company in 1911 to create a resort.

One of his partners, Charles M. Roser, invested the money he made from selling the Fig Newton cookie recipe to the National Biscuit Company (Nabisco) for a million dollars in 1910.

Funds from the gigantic cookie sale helped build the island’s first streets, sidewalks, vacation cottages, water system, a dock for steamships at the end of Pine Avenue, and a bathing pavilion where the Sandbar Restaurant is now located.

A few years after the Beans settled in Anna Maria, Samuel Cobb, and his wife, Annie, homesteaded 160 acres and reportedly produced the island’s first white baby in 1897. Cobb also spawned its first businesses, Cobb’s Marine Ways, a marina, and The Club House on the Gulf with sleeping rooms, showers, and dining hall, 1907.

The Cobb baby, born in 1897, was named Anna Maria. The island itself was named long before homesteaders arrived.

There are different versions about how it was named. Two are told on a plaque at the history museum.

According to one version, the Spaniards, who first claimed the island, named it after Maria, mother of Christ, and her mother, Ana, following Spain’s custom of giving sacred names to places.

However, the “Scottish theory” offers another possibility. In the mid 1840s a U.S. survey team stayed at the home of the Scottish Post family in Tampa. To thank them, the crew named the island after Madison Post’s wife, Maria, and her sister, Anna.

Old Spanish maps marked the island Ana Maria Cay; an 1855 U.S. map names it Anna Maria Key.

An 1894 homesteader, Captain John R. Jones, officially registered the name, Anna Maria, on federal records.

Shells Saved Post Office; Model Ts Instead of Ships

The Bean-Cobb-Roser era was a time of firsts.

* Sam Cobb ran the first post office from his home, starting in 1902.

When H.T. Watson became the next postmaster, he came up with a plan to keep a post office running. So as to have enough postal receipts to support a post office for a sparse population, Watson kept mailing shells to relatives in England.

* Charles S. Roser’s father, John M. Roser, had the first church built in 1913 as a memorial to his late wife. Ministers from different denominations came by boat to conduct services. The Roser Memorial Church still stands on Pine Avenue.

* The first schoolhouse was also built in 1913 on Magnolia Avenue. Anna Maria, still a one school island, has a bigger school in another location.

* In 1922 travelers to the island no longer had to wait for steamships or shout for ferrymen across the bay to the Village of Cortez. The first bridge linking the island to the mainland was finished that year.

The rickety wooden bridge was manually opened and closed with a crank. It was wide enough to accommodate Model-Ts.

Today a fishing pier with an Anna Maria Oyster Bar remains in Bradenton Beach where that bridge once stood.

Back in the 1920s, the wooden bridge revolutionized the area then known as Cortez Beach. Bridge Street became the commercial center of the island.

By 1927 Cortez Beach had a population of 75, including carpenters, bookkeepers, bootleggers, and prostitutes, according to the historical society’s book on early history. It also had a village store, a gas station, the Bayside Inn, the Bath House, and the Pagoda Dance Hall.

During that era bath houses rented out woolen bathing suits. The island’s history museum preserves swimsuits from that period.

Contractors Flee with Funds; 150 Acres Cost $25,000

A second bridge out of Anna Maria was built in 1926, this time from the south end of the island to Longboat Pass Key. However, just a few years later, the bridge was lifted off its foundation by high tide, strong winds and swift current in 1932.

Finally in 1941 a group of Tampa men decided to raise funds to rebuild the bridge.

Some 17,000 people reportedly attended the fundraiser, danced to live music, and watched a golf exhibition. A tight rope artist performed 20 feet above Longboat Pass between Anna Maria and Long Boat Key, and he stopped midway to do a handstand.

The event was successful but the men contracted to build the bridge disappeared with all the funds. A modern bridge to Longboat was not built until 1958.

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Construction accelerated during the next decades. Trailer parks, motels, and restaurants were established as well as unique entertainment facilities.

Fast Eddie’s attracted customers by advertising, “Warm Beer, Lousy Food,” according to the original sign at the island’s history museum.

The Mira-Mar Pavilion of 1940, a restaurant, bar, and bathhouse, was later purchased by professional comedians, June Burnett and Bob Sheldon. They performed there, and it became a night club.

It was known as the Monkey Bar because of the stuffed monkeys of different sizes and shapes hanging from just about every inch of roof and ceiling. Eventually it became Trader Jack’s with a circus show and short versions of Broadway hits.

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Meanwhile, Anna Maria was spring training ground for baseball players in the 1940s, 1950s, and the early 1960s. They were dubbed “boys of the winter.”

Development slowed during World War II while soldiers were trained on the island. Also, the military planes flying over the beach discouraged visitors.

Practice bombs exploding on nearby Mullet Key and Passage Key disrupted the tranquility of the island. At times Anna Maria’s skies turned dark. Just before D-Day an armada of bombers rehearsed for the invasion of Europe, and Hugh Holmes Sr. recalled, “500 of them covered the sky, almost blacking out the sun.”

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Once the war was over, developers bought land that was still cheap and abundant.

For example, Peter Mickelson and his partners purchased 150 acres for $25,000 in 1946 and tore down swamps full of mosquitoes and rattlesnakes, according to Carolyne Norwood’s “Anna Maria Island, 1940-1970, Tales of Three Cities.”

Three Cities, One Island, Death Rattle Bridge Replaced

Meanwhile, the island, seven miles long, became three separate cities.

The City of Anna Maria at the north end was incorporated long ago in 1923. The City of Holmes Beach in the middle of the island was incorporated in 1950, and the City of Bradenton Beach to the south was incorporated in 1953.

Still, the threesome comprised one island, and so, together, citizens discussed the pros and cons of building bridges on the pages of The Islander newspaper, founded in 1951.

According to Norwood’s book, islanders wanted to attract northern tourists but the rickety old bridge was a deterrent.

In the 1940s, Manatee County residents also wanted to go to the beach but the bridge with “the death rattle in its boards” discouraged them from coming, according to Norwood. The island then had a population of 800.

“We rattled over the decrepit bridge, which sounded like the castanets of an inebriated Spanish dancer, only amplified a thousand times,” a citizen wrote in a 1953 letter to the editor in The Islander. He noted that the price of replacing the rotten boards each year was probably as great as the cost of the interest to finance a new bridge.

At that time traffic would stop while it took 15 minutes for just one small boat to pass under the bridge.

Citizens also vented their views in The Islander on whether or not to build a bridge connecting Manatee Avenue to Anna Maria.

After a few years of debate, two concrete and steel bridges were inaugurated in 1957, the Cortez bridge, and then the Manatee bridge.

Elephants with bathing beauties on their backs were the first to cross the new Cortez Bridge. Then a carnival with street dancing, circus acts, and water ski show entertained 4000 people.

Of course the bridges spurred further development, including a golf course inaugurated in the 1960s and more homes, including apartments, then a new concept on the island.

Land for sale tripled. Developers who bought large tracts of land for a few hundred dollars divided their land into lots and sold them for $3000 or more.

Tolls ‘Rest in Pieces,’ Island Says No to High Rises

In 1964 the collection of tolls (30 cents) was discontinued on island bridges. Islanders celebrated. A ribbon was cut, and a black casket with a wreath of old toll receipts was placed beneath the sign, “Rest in Pieces.”

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Meanwhile, construction had its limits. In 1970 and 1971, two buildings were erected in Holmes Beach, Martinique Condominiums, the island’s first and last high rises.

“No more,” the town decided immediately by passing an ordinance banning high rises. The cities of Bradenton Beach and Anna Maria had already passed similar ordinances.

So today the island still preserves its small town look with multi-colored cottages snuggled in greenery.

The turquoise sea has remained a constant throughout the centuries, and today’s beachgoers are reminiscent of the scantily clad, tattoo-covered Tocobagan Indians encountered by Spanish explorers.

However, ships no longer bring vacationers to the island but a 1923 advertisement for boat trips has a message that could still hold true.

In the ad hanging in Anna Maria’s history museum, a woman in a woolen bathing suit daringly reveals her knees while Adams Boat Line sells its excursions to Anna Maria by saying, the visit will be “a pleasant memory if you take the trip, a lasting regret if you do not.”

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Volunteer Opportunities in the Community

There is no better way to be a part of our island community than to volunteer and get involved. Residents, both annual and seasonal, as well as our many visitors all uniting for the common good is what makes Anna Maria Island so special. Volunteer opportunities abound on the island and the surrounding areas. From cleaning the beaches, to monitoring nesting sea turtles, preserving the area’s unique history, supporting our youth and those in need, and so much more, there is something for everyone. Find a cause or non-profit you enjoy and get involved!