The history of Useppa Island

April 14, 2014 | South Tampa Magazine | Categories: Editorial, History | Tags: Barron Collier, Collier Inn, Gar Beckstead, Useppa, Useppa Island


On this island, there are no cars, no bridges and no crowds. Owner Gar Beckstead shares what makes his private island club so extraordinary.

Story by: Erika Vidal Holmes

Gar Beckstead spent his first night on the island on the front porch of a broken down cottage. The 1.5-mile long body of land was nearly deserted, structures were dilapidated, sidewalks overrun by vegetation.

“The jungle had reclaimed it,” he says.

Two days later, the 35-year-old flew to Europe, resigned from his cushy consulting job, married his Japanese girlfriend and returned to the U.S. to live on a little island and “cut the jungle.”

The year was 1976. The island was Useppa.

Beckstead, now 71, recounts the tale over a glass of pinot grigio and a plate of meatloaf and mashed potatoes piled high on Texas toast, today’s special at Useppa’s famous Collier Inn. Through the window behind him, the wind wrestles a palm tree against a cloudless sky.

“Why Useppa?” someone asks.

“Everybody has a story as to why they came to Useppa,” he says.

Beckstead’s begins as a business venture and ends up a love story.


Located in Lee County, Useppa is a barrier island within the isles of the Southwest Florida coast, a few miles south of Boca Grande and accessible only by boat or seaplane. Legend has it notorious pirate Jose Gaspar used Useppa to imprison a Spanish princess named Joseffa. When she refused to return his advances, he killed her, and the island became known as “Joseffa’s Island,” which eventually evolved into Useppa.

“I don’t believe any of that,” Beckstead says, “but the middle name of my first-born daughter is Joseffa.”

The real story isn’t as dramatic.

“The best we can tell, it was a phonetic pronunciation of the [name of the] family that for several generations lived on Useppa,” he says. “It was an Italian-Spanish family; they ran the fishing camps.”

Giuseppe Caldez was the patriarch.

During the last 200 years, Useppa has gone from resort to military outpost and CIA training ground and back again. Beckstead and a handful of adventurers purchased it in 1976, restored it and developed it. Today, Beckstead and his wife, Sanae, are the sole owners of Useppa Island Club, which serves Useppa property owners and club members exclusively.

Beckstead says keeping the island private is a “protective device” grounded in preservation and community rather than glitz and greed. He decided early on he didn’t want to run the sort of the island that serves as a beer-and-burger pit stop for boaters and anglers. Nor did he want it to be an over-the-top luxury resort that disregards its historic significance.

“We don’t serve mai tais in bikinis by the pool,” he says.

Useppa Island Club is a refined, intimate community of 115 homes and 101 property owners. The island is home to the marina-front The Tarpon Bar, tennis courts, croquet lawn, fitness center, the Izaac Walton Fishing Club — founded in 1908 and considered one of the most exclusive in the world — and The Collier Inn, a century-old building that served as Barron G. Collier’s primary residence.

Collier owned Useppa from 1906-1939 and is famous for building the Tamiami Trail, which connects Miami with Southwest Florida. In those days, Useppa attracted guests such as the Vanderbilts, Rockefellers and President Herbert Hoover.

Even today, the island’s laid-back luxury lifestyle draws a distinct breed.

“It’s not just a demographic,” says resident manager Chad Cadwell. “It’s anybody that is not into the bling. This is a place where you take your cell phone and turn it off and grab a Kindle. You could be sitting next to a [big-time] CEO and never know. People here are low key.”

To Beckstead, part of life here is mastering the art of doing nothing.

“People come here because they’ve been to all the other places,” he says. “If you ask a Useppa person, ‘What do you do when you’re here?’ The answer is, I have no idea, but all I know now is at the end of the day (or week or month), there’s never enough time to get it done.”

Part of Beckstead’s mission has been to research, preserve and restore Useppa’s history and prehistory; the island has been continuously inhabited for 10,000 years beginning with the Calusa Indian civilization.

In 1976, his first task in bringing the island back to life was figuring out what not to kill. Clearing the land was like disarming a bomb, and Beckstead hired a horticulture expert to help figure out which wires to cut.

“The vegetation was very special,” he says. “The whole island was covered with jungle, so you had to figure out what not to cut back, while opening it up.”

Next, he restored 1,700-year-old structures — all in disrepair — built new homes and established strict deed restrictions to ensure new architecture was consistent with the old. Though they keep with the Old-Florida style, these homes are by no means outdated. Many are extravagant, and outfitted with the modern interior amenities of a new custom home.

While sprucing up the island’s surface, Beckstead began uncovering its prehistory through archaeological digs in conjunction with the University of Florida. Eventually, he helped establish the Barbara Sumwalt Museum, which tells Useppa’s story from the Ice Age to the present.

For Beckstead, the key to balancing preservation with modern luxury comes down to choosing the right path.

“You just have to make sure when you come to the forks in the road — and they always come along — where you can do some development that you shouldn’t do, you make the right decision,” he says. “Trying to do that and make a living is not easy. I could have gotten very rich off this island by doing it very differently.”


In two years, Beckstead will have owned Useppa Island longer than anyone else.

Standing inside the island’s museum, examining Collier’s photograph, Beckstead realizes for the first time he was born the same year Collier ceased ownership (1939).

“Maybe that’s why I was born,” he says, “to one day take over the island.”

Beckstead is certain no other life’s work would give him the sense of satisfaction Useppa has. As he grows older, part of his job and one of his greatest concerns is finding someone who feels the same. He is unsure what the island’s future holds or who’s next in line to own and care for the “complicated asset.”

“I have thought about the answer to that question for so long,” he says.

The one thing he knows is that he would rather give Useppa away to someone worthy than sell it to someone who would break its spirit.

A friend once wondered how Beckstead would reply when he reaches “the great beyond” and someone asks, “What did you do with your life?’”

That, he responds while leaning back in his chair, is simple.

“I,“ Beckstead says, “did Useppa.”


Though Useppa is a private island resort, it welcomes visitors and guests of members.

Day Trip: Captiva Island Cruises offers daily cruises and tours of Useppa Island. Learn more at or call (239) 472-5300
Sleep: The Collier Inn allows one stay per year for non-members and two per year for guests of members; all residences are privately owned, but many are available for vacation rentals.
Eat: The Collier Inn; Tarpon Bar
Explore: Barbara Sumwalt Museum; Palm Garden; a stroll along the Pink Promenade, a sidewalk originally constructed of shell and pink sand in 1903
Membership: Levels and options vary; the island hosts a Get Acquainted program offering non-members a glimpse of Useppa Island life. For more information call (239) 283-4227.

For more information and complete directions go to or call 239.283.4227.