Gasparilla Inn: Classic, yet modern

The Gasparilla Inn

BOCA GRANDE, Fla. – The late William F. Buckley Jr. famously declared it his mission to “stand athwart history yelling ‘Stop!’ ” Buckley almost certainly would have loved The Gasparilla Inn & Club.

In a time of steadily eroding standards, The Gasparilla Inn represents a haven of civility – refined, but not stuffy, elegant without being ostentatious. It’s a place where men are expected to wear sportcoats to dinner, but don’t need a tee time to play golf; where guests stay in a nationally designated historic property while still enjoying the full menu of modern resort amenities; and where American royalty (the Bush family visits regularly) mingles with the commoners.

The Gasparilla Inn, located midway between Sarasota and Fort Myers, opened in 1913. The fact that it maintains such a strong connection to its past likely reflects two facts: It effectively has been controlled by only two families over the past 80 years, and Boca Grande is a place where time moves slowly. 

“There’s something about that old Florida feel,” says Jack Damioli, The Inn’s president and general manager. “Others have tried to re-create it, but it exists naturally here.”

Damioli spent 22 years at The Greenbrier, starting in the clubhouse bag room and rising to be the general manager. Five years ago, a recruiter urged him to visit The Gasparilla Inn, which then was searching for a new president and general manager. The recruiter told Damioli that he’d feel right at home, that The Gasparilla Inn was a smaller version of The Greenbrier, but in need of some love. The Inn’s decor was even reminiscent of The Greenbrier’s bright and cheerful Dorothy Draper furnishings. Damioli finally agreed to check it out. 

“I saw the bones of a great resort,” Damioli says. “It just wasn’t assembled in the right way.”

The inn had the charms of old Florida, but its systems were just plain old. At the time, it had no website, no point-of-sale system, no human resources or catering department and no ability to process credit cards. Damioli addressed each issue and also began cherry-picking managerial talent from The Greenbrier.

One thing that didn’t need any fixing was the golf course. Pete Dye oversaw renovations to the course in 2004-05, including the installation of salt-tolerant Paspalum turf. When Damioli first toured the course with superintendent Jeff Strother, he did suggest chopping down a bare tree on the third hole, but thought better of it when Strother raised this question: “Where will the bald eagles go?” The tree still sits in the right rough.

Dye, reworking a 1928 design, efficiently packed a 6,811-yard layout and full practice facilities on a 106-acre island that’s adjacent to the hotel. Wind is a constant, but its direction is not.

“It’s like playing a different course every day,” says Howard Wise, a Birmingham, Ala., steel executive who spends about half the year in Boca Grande. The breeze is just as likely to come out of the west, off the Gulf of Mexico, as it is to come from the east, off Charlotte Harbor. On a recent visit, gusts up to 25 mph literally stopped seagulls in midair near the 14th tee, the start of a dramatic three-hole plank walk heading south along the harbor. 

Just across the bayou from the golf course, the Inn Marina is undergoing an expansion that will double the size to 214 dry slips and 14 wet slips. A few hundred yards away, at the Beach Club on the Gulf side, guests train in a fitness room overlooking the beach, then pamper themselves next door in the nine-room spa.

Such luxuries have helped The Inn to mature gracefully, which is evident in the fact that some guests first visited decades ago. But they also have broadened the resort’s appeal to a new generation.

“We’re 97 years old,” Damioli says, “and really being discovered for the first time.”

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