Boca Grande: Florida’s Most Laid Back Retreat For The Rich

Once I ordered an ice cream at the converted railroad depot at Boca Grande and behind me an elderly woman with white hair and huge sunglasses remarked, “That looks good.  I’m going to get one.”

It was only as I watched the lady leave the store and waved to a man on a bicycle that I realized I just met former First Lady Barbara Bush.  That’s the way things happen at Florida’s most laid back hideaway for celebrities and the wealthy.


BOCA GRANDE, located on a dual county island at the mouth of Charlotte Harbor, is best known as America’s tarpon fishing center. Once a small phosphate export port, Gasparilla Island remained famous for its tarpon fishing plutocrats until the construction of a private toll bridge by Robert Baynard in 1955.

The discovery of the isolated island’s charms by successful Florida professionals meant  the building of expensive beach villas.  Even today this is an island with no high rise hotels and condos, no fancy nightclubs, and a downtown that still resembles a small fishing port.

WHERE TO START: Start in front of the island’s pride, at the corner of Fifth Street and Palm Avenue, the: (1) GASPARILLA INN(1912), a large pale yellow frame Victorian hotel with a Classical portico and a colony of cottages and rooms built around the golf course.


An Arcadia phosphate executive Peter Bradley allied with James F. Gifford, President of the Charlotte Harbor and Northern Railroad, to build the luxury winter resort. It’s hotel registrar may still read like a “Who’s Who”, but you won’t get to read it for low key privacy is the rule here.

DRIVE EAST ON FIFTH AVENUE along the golf course toward Boca Grande Bayou.

flordatraveler bocamap

TURN RIGHT ON BAYOU AVENUE toward HARBOR DRIVE and the yacht basins. Here are charter boat centers and places to stop for lunch. In tarpon season there will be fishermen from around the world. Once in the peak of the winter, Katherine Hepburn was observed eating with some retired school teachers.

CROSS WEST AVENUE past the  (3) COMMUNITY HOUSE and the (4) COMMUNITY CENTER. PASS PARK AVENUE and TURN RIGHT ON GILCHRIST. THEN, if your car fits, TURN RIGHT ONTO (5) BANYAN STREET, an amazing gnarl of shady banyan trees planted on both sides by Peter Bradley.

TURN LEFT ON PARK AVENUE. On your right is the interesting: (6) OUR LADY OF MERCY MISSION CHAPEL, a replica of a Spanish style mission with brick floors, but featuring a circular entrance way. You should stop to go inside to admire the fine woodwork and the real Madonna Icon of Russian design.


GO TO THIRD  STREET. On the corner to your right is the (7) BOCA GRANDE THEATER (1924), once used as a restaurant and now a local theater showplace. As you enter you’ll see an unusual open atrium, an odd theatrical design.

A few doors down is the (8) CHAMBER OF COMMERCE. At the end of the block on your right is the POST OFFICE. On your left is (9) FUGUTES (1916), the town’s mini-everything store founded by Jerome Fugate Sr., and visited by everyone sooner or later.

Across Fourth on the right is the wonderful  (10) BOCA GRANDE RAILROAD DEPOT (1910), an impressive two story structure which now houses antique and gift stores and an ice cream parlor/restaurant. The brick structure with the arcaded loggia was the last depot for the Charlotte Harbor & Northern Railway.


TURN LEFT ON FOURTH AND LEFT ON GILCHRIST AVENUE, the route to the southern tip of Gasparilla Island. On your left is the (11) ST. ANDREWS EPISCOPAL CHURCH, a country-style church. Go inside to view the round stained glass window over the alterand notice the communion rail kneelers in needlepoint.

At the end of the block is the (12) UNITED METHODIST CHURCH with a plaque to Mary Frances Thompson. A HALF MILE DOWN Gilchrist you’ll see the (13) COAST GUARD LIGHTHOUSE (1927), a narrow electric beacon designed to replace the notable antique. at the island tip. Across the street was the site of the BOCA GRANDE HOTEL (1930), a three story, 200 room resort by Italian immigrant Joseph Spadara. Hurricane Donna destroyed it in 1960.

CONTINUE DOWN TO THE SOUTHERN BEACH to the 13 acre Gasparilla Island State Park. You’ll have to walk down the beach to the beautiful (14) GASPARILLA ISLAND LIGHTHOUSE (1890) and its matching keeper’s house. By the parking lot is a little seaman’s CHAPEL popular for waterside weddings.  This is my favorite lighthouse in Florida, not just because it was near where I lived in Englewood, but because there is a museum inside and it has two neat structures.  A 145-mph hurricane went across the island and sucked souvenirs goods out of the gift shop, but didn’t hurt the structures.


SHELL COLLECTORS SPECIAL: STOP BY THE JOHANN FUST LIBRARY (1949) on Gasparilla on 9th Street to see the shell collection donated by winter resident Henry Francis DuPont. Another interesting spot is JOURNEY’S END (1914), on the Gulf at 18th Street, a complex of four two story cottages built of virgin pine from Arcadia.

About floridatraveler

Historian and travel writer M. C. Bob Leonard makes the Sunshine State his home base. Besides serving as content editor for several textbook publishers and as an Emeritus college professor, he moderates the FHIC at
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