A Capsule History of Estero Island Part 2


Sands of Time: Growth, Development, Booms and Busts

Visitors and residents in 2019 may find it hard to picture Fort Myers Beach as an uninhabited stretch of sand and mangroves. But after the native Calusa people were killed or run out of southwest Florida by the 1700’s, this 7.5-mile island on Estero Bay remained an uninhabited, transient fishing outpost for nearly 200 years.

In 1865 only the Ellis family officially resided on Crescent Beach – as Estero Island was then known – farming a homestead around the Mound House (which they sold to Robert Gilbert in 1898). Other homesteaders trickled in through the first decade of the 20th century.

The island welcomed its first official tourist lodgings in 1912: the grand, 3-story Winkler Hotel. Guests arrived and left by boat, disembarking at the long pier (posts from the rebuilt pier still stand). They dined at the only local restaurant, in the hotel. The island’s modest popularity as a vacation spot likely traced to early Fort Myers seasonal resident and avid fisherman, Thomas Edison.

Organized development on the island began slowly, as original homesteaders sold off portions of their holdings. Wrote Rolfe Schell in his 1980 History of Forty Myers Beach Florida:

“In 1911 the first semblance of development, as we know it today, was started by Harold C. Case. It was about a mile and a half wide piece of property with Connecticut Avenue in its center. At that time, the shell road ended at Connecticut Avenue. In order to travel farther southward you turned onto the beach, which at low tide could accommodate six-lane traffic.”

In 1919 homesteaders E.E. Damkohler and C.S. Fickland started the Seagrape Subdivision on Mango and Chapel Streets. A few miles south, an airfield, on the site of the now-defunct Fort Myers Beach Golf Club, opened to fly-in tourism on a micro-scale. The sleepy little island started to attract notice.

The first bridge to Crescent Beach, a wooden lift bridge, opened in May 1921. Only one car at a time could traverse the narrow span, at an eyebrow-raising toll of 50 cents per car plus 15 cents per passenger.

That year Captain Jack DeLysle, a flamboyant entrepreneur and rum runner, built a 3-story resort plus the Seminole Sands Casino and dance pavilion on the Gulf side of Connecticut Street. In July 1921, local resident Tom Phillips and Chicagoan Harry Fiedler dug the island’s first canal at First and Crescent Streets.

A story in the Fort Myers News-Press in early October 1921 proclaimed:

The Seminole Sands Casino and dance pavilion on the beach at Connecticut St, was a popular destination in the 1920’s.

“Crescent Beach Center of Most Intense Development in Florida Today.” The island’s population stood at 62 souls.

Winds of Change

On October 26, 1921 a severe hurricane lashed the island; perhaps the worst since 1873.

Wrote Rolfe Schell:

“The grassland at the Beach was pushed back a hundred feet and considerable damage was done to the few buildings located on the island. The Seminole Sands Casino and bath house were ruined as were several cottages. The road on the mainland, which paralleled the shore, was destroyed.”

After 18 months of rebuilding, the island was back in business. In June 1923, over 200 cars passed over Matanzas Pass Bridge in a single day. The Miramar and Gulf Heights Subdivisions opened in 1925.

But the 1920s’ almost yearly tropical storms kept taking bites out of the boom. Hurricanes in ’24 and ’26 left the lift bridge so damaged that it was replaced in 1928 by a 50-year-old, second-hand swing bridge with a hand-cranked (and cranky) mechanism.

The 1926 storm blasted out Hurricane Pass, creating San Carlos Island (formerly part of the mainland), and demolished a budding subdivision called San Carlos on the Gulf. The budding boom collapsed after a 1928 hurricane wiped out most of the flimsy buildings on Fort Myers Beach. Development on the island ground to a standstill for the next 7 years, not helped at all by the Great Depression that started in 1929.

Wrote Rolfe Schell: “In 1935 at Canal 1 they had a sale of lots. . . . but nobody would bid the necessary $50 per lot. So they closed the auction because the highest bid they got was $35.” Schell soon purchased a double lot on Delmar Street for $2 per foot; a total price of $160.

The island held so few buildings that houses had no addresses and were designated by the names of their owners. Everyone who owned a place here knew each other.

The late 1930s’ peak season population was estimated at 400.

Early Businesses and Hotels

Driving and parking were done on the beach in the 1920’s. Shown here, gridlock at the Seminole Sands.

The first marine facility was Sander’s Boat Yard, started in 1905 by George Sanders, an original member of the Koreshan Unity who renounced the sect. It’s now the location of Snook Bight Marina, Bayfront Bistro and Publix.

An early retail establishment – Thompson’s Juke Joint, built in 1933 – housed a jukebox and drug store with soda fountain. The distinctive stucco structure, which for many years was a fabric store (The Cotton Shop), still stands and is now home to the Cigar Hut.

Silver Sands became the island’s first cottage court motel, built in 1921. Beachside and bayside cottages and fish camps popped up to serve tourists over the next four decades.

The massive Commodore Hotel – built of whitewashed coquina-rock blocks, with imposing pillars and a grand lobby – appeared on the shore in 1938, where Smuggler’s Cove condo stands today at 5100 Estero Blvd.

During WWII years the Commodore Hotel hosted military men on leave. On Sunday afternoons, the Commodore offered bathhouses, cold sodas and beer, hotdogs and hamburgers, with dancing on the Gulf-front patio.

With the war, new visitors arrived on Estero Island: soldiers and airmen. The airfield at Buckingham became a gunnery school; Page Field in Fort Myers was a flying school. A number of military officers and their families stayed out on “The Beach,” where wartime regulations froze rents as low as $45 per month, all-inclusive.

After the war’s end, the rent freeze thawed, rationing disappeared, and tourists flowed in growing numbers onto the quiet island paradise.

The Skyline and Rancho del Mar motels opened in 1949. Developers dredged canals and used the muck to create higher ground for more cottages and motels. Calusa Indian mounds fell to bulldozers, their contents crushed into fill for the growing network of roads. Archaeology and historic preservation weren’t yet on the radar.

Aerial view of Fort Myers Beach from the 1960’s looking north from the south end of the island. Photo courtesy of Estero Island Historic Society.

By 1950 the Estero Island population stood at 711. Development continued apace, with little long-term planning or vision. In 1959 the Privateer opened as the first three-story “high-rise” co-op apartment. It later changed to interval ownership, as did the Sandpiper and Neptune Inn motels.

By 1960, the island’s population had jumped to 2,464. More restaurants and shopping plazas appeared. The south-end Big Carlos Pass bridge to Lovers’ Key, Bonita and Naples opened in 1965. Traffic increased and growth accelerated.

The island’s population pegged at 4,305 in 1970 when Leonardo Arms opened as the first condo at the south end, followed by Island Towers in 1971 at the north. The 65-foot-high Matanzas Pass Skybridge opened in 1979, sparing millions a wait for the balky swing bridge to function. But it did not spare the island from seasonal traffic back-ups.

By the turn of the 21st century the Fort Myers Beach permanent population reached 6,844, of which 5,614 were housed in condo units by 2013. Visitors swelled the numbers in season to over 45,000.

The most recent land bust that started with the 2007 recession had turned around by 2014. Property values soared again, and the old-style beach cottage surrounded by  tropical foliage began giving way to large new homes that occupy every possible square foot of their lot “under air.” The good times roll on. Until the next major hurricane or financial crisis, perhaps.

Come what may, it’s still a slice of paradise.


By Janet Sailian