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The Pete Dye Signature 18-hole, 72 par championship golf course at the Gasparilla Golf Club, located on scenic Charlotte Harbor.

It’s a balmy weekend, ideal for a quick getaway to that idyllic Old Florida town of Boca Grande, on Gasparilla Island south of Englewood.

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 has managed to retain its many unpretentious, small-town charms while the rest of Southwest Florida has exploded with growth and modernization.

We’re here to decompress with a bike ride around seven-mile Gasparilla Island (a mere mile wide at its widest), spend an hour or two at the beach at sunset, poke in and out of some delightful mom-and-pop-owned shops, devour a fresh-off-the-boat grouper sandwich, and enjoy a stay at the gracious Gasparilla Inn & Club, founded in 1913 and on the National Register of Historic Places.

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 world. From 1907 to 1979, a railroad ran through its center, carrying that phosphate to waiting ships at the island’s southern end. 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 will demolish the structures on the property and maintain it as a nature sanctuary. More than 1,000 people contributed to the purchase, including residents who made multimillion-dollar donations.

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The Boca Grande Lighthouse and Museum.

They’re also proud of the quality of local waters. Boca Grande is synonymous with sport fishing, of course, and Cappy Joiner, president of the Boca Grande Fishing Guides Association, says the No. 1 reason is the water. Charlotte Harbor is a big bay, and on the whole left side there are no residences (and therefore no septic systems or fertilizer-fed lawns to pollute the water). Boca Grande Pass itself is over a mile wide and in some places 86 feet deep; “a lot of bait travels in and out,” Joiner says. 

From April to late July, and sometimes into August, the pass teems with tarpon, as many as 10,000 at any one time according to a scientific study, Joiner says, each weighing anywhere from 50 to 200 pounds. The rest of the year, the 39 members of the fishing guide association take tourists out to catch redfish, trout, cobia, snapper, grouper—“pretty much all the saltwater species,” he says. Joiner, born and raised on Boca Grande, will be 80 years old in June, and he says he’s guided fishermen from Japan, China, Australia, New Zealand, all over Europe and Mexico as well.

The Boca Grande Chamber of Commerce hosts the annual World’s Richest Tarpon Tournament; this year’s will be May 25 and 26. Last year’s winners caught and released four of the huge, silvery sport fish and received a check for $22,000.

“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.”

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Boca Grande’s charming shopping district 

A stroll down tony Gilchrist Avenue confirms our suspicion that real estate here is pricey; and, indeed, a recent Zillow search revealed 70 homes for sale on the entire island, ranging from a Gulf-front mansion for $9.7 million to a vacant quarter-acre non-waterfront lot for $799,000. Construction is under way for Hill Tide Estates, an enclave of 19 luxury single-family homes on the former FP&L property at the island’s southern tip, starting at $1.4 million.

“The biggest change we’ve seen here is the increase in property values and the decrease in available properties,” says Shortuse. “There’s no property available for anything, building or buying.”

But we’re here to get away from it all, not to stew over property values, and our perch at the Gasparilla Inn affords the perfect way to do that. With its cheery yellow walls and bright pink, green and white tropical furnishings, this 103-year-old inn is a throwback to a more genteel time. Among its famous guests have been Thomas Edison, Henry Ford, Katharine Hepburn and the George H.W. Bush family. (They now rent a home on the island, we were told.)

The historic inn is meticulously well-maintained. Marketing director Corey Anglin explains that it closes from Fourth of July weekend to the first week of October each year for deep cleaning and all sorts of touch-ups. We were pleasantly surprised at the multiple generations of guests—doting grandmothers buttering toast for their grandchildren at breakfast, youngsters playing ping pong and backgammon in a common room off the lobby. “We take a lot of pride in that,” says Anglin. “So many guests started coming here as children, and they come back every year to the same rooms.”

“Boca Grande is a special place, and we locals are passionate about it,” says Boca Grande Chamber of Commerce executive director Wesley Locke, who grew up on Boca Grande. “I longboard on the island through town, and I smell the salt air and see all the friendly faces who’ve raised me. There’s a lot of love here.”

Locke says there’s an unspoken understanding among locals that, when they interact with the famous and ultra-wealthy visitors, “We don’t treat them any differently; they don’t want it.”

“When you see celebrities, like the Bushes,” agrees the Boca Beacon’s 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.”

That held true, Locke says, even when Harrison Ford accidentally bumped into her friend’s grandmother while he was biking on the island. “She said it was the best day of her life,” Locke says.

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The Loose Caboose restaurant.


Hire a fishing guide. The Boca Grande Fishing Association has 39 professional member-guides who can help you snag that coveted tarpon during tarpon season (April-July), or any time of year.

Shop. Several charming boutiques are conveniently located in the center of town. We especially like Fugate’s, which is chock-full of beach-themed souvenirs (, Boca Grande Outfitters for fishing gear ( and Fresh Produce for colorful vacation wear ( Hudson’s Grocery ( has a fresh fish market, deli sandwiches and wines.

Rent a bicycle. Island Bike ‘n Beach, at 333 Park Ave.,, can set you up with hourly bicycle rentals so you can tour the island. Helmets and baskets are provided free of charge.

See a show at the Boca Grande Community Center. 131 First St. W., (941) 964-2564; The regal 1920s Mediterranean complex hosts everything from newly released films to National Theatre Live screenings, lectures on history and current affairs by nationally renowned authors (United Press International editor emeritus Martin Walker will discuss “Brexit: The Bumpy Roads Ahead” on Feb. 4) and musical events, including a concert by Venice’s own Dick Hyman March 24.

Visit the Boca Grande Lighthouse and Museum. Built in 1890, it’s the centerpiece of Gasparilla Island State Park. You can tour the restored lighthouse from 10 a.m. to 4 p.m. Mondays-Saturdays and noon-4 on Sundays. Two picnic pavilions are on the property, which is at the southern end of Gasparilla Island overlooking the state-owned island of Cayo Costa. 

Check out the Johann Fust Community Library. 1040 W. 10th St., (941) 964-2488; Housed in this humble, pink 1920s building is a collection of rare books that includes a leaf from the Gutenberg Bible printed in 1454 and a page from the Book of the Dead, which, according to the library website, was written in the first century B.C. and copied onto papyrus in the first century A.D. It sums up Boca Grande’s unpretentiousness, says Gasparilla Inn marketing director Corey Anglin, “that something so deeply notable is housed in a place so deeply hidden.”

Hit the beach. Gasparilla Island has lovely, unspoiled Gulf beaches with limited parking at several public accesses. Here’s a tip from Boca Beacon editor Marcy Shortuse: After you park in the Fourth Street lot off Gilchrist Avenue, just beyond the center of town, turn left and walk down to First Street on a small path between the big orange wall and the seawall. It’s called The Promenade, and it’s been publicly owned since 1927, she says. “We have photos of women with their parasols in the early 1900s walking the beach at sunset there.”


The Gasparilla Inn & Club  500 Palm Ave., Boca Grande, (941) 964-4500; Book a tasteful room in the historic main building or in one of the cottages, villas and estate homes that surround it. There’s something for every interest: 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.


The Pink Elephant 491 Bayou Ave., (941) 964-4500; The Gasparilla Inn’s casual dining option, this lively eatery is a favorite with locals and tourists alike. (Just check out the long line of golf carts in the parking lot.) It’s winner of Wine Spectator’s Award of Excellence. Be sure to try Chef Rob’s kicky Thai shrimp with Asian slaw.

Eagle Grille and Miller’s Dockside Bar & Grill 220 Harbor Drive, (941) 964-8000; Fine dining upstairs in the casually elegant Eagle Grille; or enjoy sandwiches, salads and more downstairs on the open-air patio at Miller’s.

The Loose Caboose 433 Fourth St. W., (941) 964-0440; A fun, family-oriented lunch and dinner spot in Boca Grande’s historic train depot. Eat outside on the covered patio if you can grab a table, but check out the 186-pound taxidermy tarpon mounted proudly over the indoor bar; it won the women’s world championship tarpon tourney many years ago.

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