A second-home haven for some of America’s wealthiest families, a beach lover’s dream and a mecca for sport fishermen from all over the world, Boca Grande—that idyllic Old-Florida town on Gasparilla Island south of Englewood—retains its small-town charms while the rest of Southwest Florida has burgeoned around it.

Since it’s an easy one-hour car trip from Sarasota, people flock to Boca Grande to bike around seven-mile Gasparilla Island (a mere mile wide at its widest), spend an hour at the beach at sunset, poke in and out of delightful mom-and-pop-owned shops in the small, central shopping district and devour fresh-off-the-boat grouper sandwiches. 

And they come to sport-fish. From April to late July, and sometimes into August, the deep and mile-wide Boca Grande Pass teems with silvery tarpon, as many as 10,000 at any one time, each weighing anywhere from 50 to 200 pounds. The World’s Richest Tarpon Tournament, sponsored by the Boca Grande Chamber of Commerce each May, hands out a five-figure prize to the team that reels in the biggest fish. The rest of the year, the 39 members of the Boca Grande Fishing Guides Association take out tourists from far-flung corners of the globe to catch saltwater species like redfish, trout, cobia, snapper and grouper.

Tiny Boca Grande, year-round population now a whopping 1,700, started in the late 1880s as a deepwater port for ships that transported phosphate all over the globe. From 1907 to 1979, a railroad ran through its center, carrying that phosphate to waiting ships at the island’s southern end. (Hence the name of the popular dining spot where we ate our grouper sandwiches, the Loose Caboose, a fun, family-oriented lunch and dinner spot in the historic train depot.) The old rail bed is now part of a paved recreational trail that meanders through some of the island’s most scenic areas. 

That railroad also brought wealthy winter visitors—the du Ponts, the Rockefellers and the Astors among them. Some of their descendants still have winter homes here, and their stately Gulf-front mansions still stand, thanks to strict historic preservation rules. In fact, the entire island is protected by the Gasparilla Island Conservation District Act of 1980, which forbids structures over 38 feet high and mandates no more than five residential units per acre.  

The islanders are equally protective of their natural resources. In 2016, the Gasparilla Island Conservation and Improvement Association purchased 30 acres of waterfront property at the southern entrance to the Boca Grande Causeway for $20.6 million. The association is demolishing the structures on the property and will maintain it as a nature sanctuary. More than 1,000 people contributed to the purchase, including residents who made multimillion-dollar donations. 

 Staying the night at the gracious Gasparilla Inn & Club gives a taste of what the island’s “founding families” must have experienced. Built in 1913 and listed on the National Register of Historic Places, the inn was named the No. 1 resort hotel in Florida—and No. 7 in the United States—by Travel + Leisure in 2017. 

With its cheery yellow walls and bright pink, green and white tropical furnishings, this 105-year-old inn has welcomed famous folks like Thomas Edison, Henry Ford, Katharine Hepburn and the George H.W. Bush family. (They now rent a home on the island, we were told.) There’s something for every interest here: a Pete Dye-designed 18-hole golf course; full-service marina; Beach Club with fitness center, spa, Gulf-front pool and tiki bar; tennis club and even a croquet club with a full championship English Rule croquet court.

“It’s a unique community, and as much as things have changed, they are still the same,” says Marcy Shortuse, editor of the Boca Beacon newspaper. “It’s still a community of fishermen and billionaires, although the billionaires have gotten younger. It’s still very close, and everyone looks out for everyone else.”

There’s an unspoken understanding among locals not to treat their famous and ultra-wealthy visitors differently than anyone else. “When you see celebrities, like the Bushes,” says Shortuse, “it’s more like they’re your neighbor. You can be standing in line behind Laura [Bush] at Hudson’s [grocery store] and smile and nod.”

Insider Info

From Candy Brooks, president of the Boca Grande Chamber of Commerce and a realtor with Paradise Cove Realty

“Rent a golf cart at Dolphin Cove on Park Avenue [to] travel around Boca Grande at a pace that allows you to truly appreciate the island. That’s the main mode of transportation here.”

“The main floor of the Gasparilla Inn & Club is open to the public. it’s gorgeous. Drop in to BZ’s Bar and have a super-expensive cocktail—it’s totally worth it.”

“Spend an hour at the Port Boca Grande Lighthouse Museum to understand the rich history of Boca Grande, from the days of the Calusa Indians to the [fictional] pirate Jose Gaspar. In April, May and into June, you can see the tarpon fishing boats.”

 “Have lunch at Boca Grande Marina Miller’s Dockside. You can walk the docks and see the huge yachts of the wealthy people who come in to spend a couple of nights or a week on Boca Grande.”

“Walk down Banyan Street. Those trees were planted by the railroad executives who owned the homes that line the street. in 2004, when Hurricane Charley blew all the leaves off the trees, the current homeowners brought in arborists from all over the world to make sure those banyan trees would come back healthily.”