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The wind whips through your hair as a ferry zips through the mangroves that line Pine Island Sound.
In the distance, a small island appears on the horizon. It’s a place where cars are forbidden, where croquet is king and where, each morning, children are instructed to be home by sundown.
Once frequented by pirates and captains of industry, Useppa Island has long been a place for people looking for respite from the hustle and bustle of the mainland. But as the club’s original members reach their golden years, a new era of visitors is docking its boats and making the private island its home away from home.
“The island is going through a change,” says Pason Gaddis, the publisher of Florida Weekly and a Useppa homeowner. “I wouldn’t say it’s turned into this party island, but it’s turned into a lot more social, but still keeping with classic (appeal) of the island.”
Accessible only by boat, the 100-acre island is a private club that can be used only by its members and their invited guests. To buy a home you need to be a member, but you can be a member—a must to enjoy any amenities, even lunch—and not own a home. Membership is limited to 700. About a third of the current membership hails from Florida, primarily from between Naples and Tampa. Half of those members have families.
That means children run free, splash in the pool and clown around on the waterfront playground. But the island isn’t just a place where children frolic. There are progressive dinners, cocktails at sunset and real relaxation.
“It’s a true vacation,” says Kellie Burns, an NBC2 news anchor and a member of the Useppa Island Club. “You just recharge, and that’s why I love it so much.”
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Before it became a vacation hot spot, before John Roach built the first lodgings and before Barron Gift Collier built a golf course, there were the Calusa.
The Calusa people were among the first inhabitants of the island. According to Useppa: History, Legend and Legacy, the island was attractive to them because of “its strategic positioning as a protected, barrier island, and also as a consistent source of fresh water.” By 1750, the entire Calusa population was eliminated from the area because of the introduction of diseases and other Native American populations.
The island wasn’t vacant long; legend has it pirates may have frequented the island. In fact, the story of how Useppa Island got its name centers around one such pirate and his beautiful prisoner.
According to the tales, the pirate Gasparilla captured a Spanish noblewoman and her entourage on their way to Cuba. Joseffa, the noblewoman, and the other women were taken to Captiva Island, where she was to be held captive. But before arrangements could be made for her ransom, Gasparilla fell “hopelessly in love with her,” separated her from the other prisoners and brought her to “Joseffa’s Island.” Gasparilla visited her at the end of each voyage, but each time she rejected him. Eventually, the story goes, he became enraged with her rejection and chopped off her head.
Brian and Mary Mccolgan fell in love with Useppa Island in 1985. Among the first wave of modern island-lovers, the pair say they first visited after they saw an aerial photo of the island and were hooked. They went most weekends for 20 years and became full-
timers after Hurricane Charley swept through.
“Living here makes you young,” says the 70-year-old Mary McColgan. “It’s hard to define. The community is incredible. Everybody is your friend. It’s so small, they’re almost your family.”
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Growing up, Ryan Sampson had heard about Useppa. His family vacationed in the area, and his family used to drive by it on the boat. A few years ago, he and his wife were visiting the island with friends who were members. They decided if they could ever find the right place they would buy it.
That happened in May, and the couple and their 19-month-old son have been visiting about once a month since.
“It’s just a special place,” says Sampson, 32, who owns a commercial real estate company in Tampa.
For the Sampson family, a typical weekend includes hanging out by the pool, bocce ball after lunch and taking the golf cart for a spin. It’s also filled with “a lot of family and quality time.”
“It’s very social,” says Mary McColgan. “We have heard … from days of old that it was cliquey. It’s certainly not that.”
Continues 67-year-old Brian McColgan: “It’s all about community for me. If you come here and think you’re going to be the emperor, you’re not. You’re only important if you give and participate in the community.”
While the “group has gotten much younger” over the years, the McColgans say the atmosphere on the island hasn’t changed. The younger generation comes for the same reason Brian and Mary McColgan first came to Useppa Island: total relaxation.
“They come here because they can’t find Old Florida anywhere else,” says Brian McColgan. “It’s very impromptu. It’s easy.”
Pirates and a long extinct native population may color the island’s past, but captains of industry put it on the map.
John M. Roach bought the island in 1894. The Chicago streetcar mogul made his home on the highest point of the island and built a 20-room hotel, called the Useppa Inn, where his wealthy friends and tourists stayed. In 1911, Barron Gift Collier visited Roach on the island. He bought it from Roach that same year.
The Colliers made the island their winter home. He entertained guests at the hotel, then called The Tarpon Inn; began the island’s Izaak Walton Fishing Club; and even built a golf course, now shuttered because of lack of use.
Collier’s purchase of the island marked the first of many modern sales. Over the years, the island changed hands several times. Each owner made tweaks, and in 1976, Garfield Beckstead purchased the property. The Beckstead family still owns the island and remains dedicated to improving it.
The pink path winds its way around the island, beyond the giant banyan tree and past the cottages with names like Egret, Ibis and Banyan.
Pason and Renée Gaddis’ home, Seas the Day, is located next door to the historic Collier Inn. The couple bought the house in 2014 and started a massive renovation and restoration with Renée, an interior designer, at the helm.
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“We were renting on the island one weekend and saw a house for sale. We were not planning on buying on the island; the thought hadn’t even entered our heads,” says Renée, 39, in an email. “We walked through the house and made an offer on it that same day. As we left the house, there was an owl and her baby in the tree on the path and I knew it was a sign.”
The house had good bones, but it was in disrepair. They tore down to the studs and began renovations, which Pason Gaddis, 40, said was a bit difficult since all of the materials needed to be brought in by barge.
Supplies to renovate a house aren’t the only things that need to be brought in on a boat. The ferries shuttle mail and haul deliveries, like food for the restaurant and booze for the bar, back and forth. There’s no such thing as a quick trip to the grocery store or a spur-of-the-moment decision to catch a movie on a Sunday afternoon. Those things take planning, a 15-minute boat ride and patience in season when there’s bumper-to-bumper traffic.
But for island-goers, the chance to cast off the daily grind is the main appeal.
“It’s sort of an adult summer camp,” says Jeff Powell, an Alabama resident and Useppa homeowner.
The Powell family found the island in August 2014. They saw a sign that said “private island,” started looking into the community and were immediately drawn to it. They lived there full-time from December 2014 until last August, but moved back to Alabama after seven months.
His children—a 7-year-old and a 10-year-old—still consider it their home, Powell says, and when the family is there the kids spend the weekends bumming around the island with their friends. And while Powell and his children keep in touch throughout the day, he rarely worries about what his children are up to.
“We feel safe with the kids out there,” says Powell, 42 and the president and managing partner of First Baldwin Insurance in Alabama. “Everyone looks out for each other.”
Miss one too many yoga classes? Someone will ask where you’ve been as you pick up a newspaper. Don’t show up for something? Someone will show up at your door to check in. Invitations to dinner parties or cocktails are always extended, even if time and time again you can’t make it.
“Everyone waves, everyone is cordial,” Powell says. “There’s a sense of community.”
There’s also a sense of fun. Croquet matches are normal activity, with tournaments popping up on the weekends. People bounce from house to house, for pig roasts and cookouts. There’s television and Internet on the island, but most people prefer fishing and reading on a porch to Netflix and surfing the Web.
“It is completely different than any other island I have been on,” says Renée Gaddis. “It is not overpopulated or commercialized. We go there and feel as though it is our own little secret escape. Shh … Don’t tell anyone about this little slice of heaven in our own backyard.”
