“The Inn,” as it’s called by the regulars, is a grand, columned wooden manor house in the Old Florida style, built in 1913 on Boca Grande, a narrow island 53 miles south of Sarasota. There are some romantic old houses and two blocks of mostly mom-and-pop shops on Boca Grande, population 973, where the citizens, hair always in place and linen shirts never wrinkled — glide around on golf carts.
The Inn is very much the center of this cozy world, and for most of its history, a newcomer could book a room only with a personal reference from a regular guest. Now, however, the doors are open to the public, though phone bookings are still preferred. Today, vacancies are rare — don’t plan on coming here for Thanksgiving next year.
It’s impressive, since hotels like this face the delicate task of staying fresh while appearing not to change. The Gasparilla is among the last of the classic country club resorts, along with the Greenbrier in West Virginia and the Cloister and Lodge at Sea Island in Georgia, where good manners are everything.
The guests, who share an enthusiasm for pink, come largely from the Midwest and the more Cheeverish suburbs of the Northeast. One of the interior decorators, Mimi McMakin, a Palm Beach native, calls it “the place for well-heeled bare feet.”
Old Florida style means a lobby that feels like a living room, with old-school Lawson sofas alongside Bar Harbor wicker, and sprinkler pipes wrapped with raffia. The 142 rooms, suites, and two-bedroom cottages are a beachier version of everybody’s houses back in Winnetka and Darien, with white-painted furniture, cheerful colors, and tiled rather than marble bathrooms. You’ll find shells everywhere: on the lamps, the candlesticks, and the cocktail tables. Throw in a stuffed tarpon and a tole pineapple lamp, and there you have it — a look you think you’ve seen before, but authentically done here, and pretty magical.
The Old Florida atmosphere is especially thick in the restaurant, with its slowly rotating ceiling fans, starched white linens, and silver-domed butter servers; in BZ’s, a clubby bar paneled with pecky cypress; and in the Pelican Club Room, the rare, masculine corner of this hotel, where for a moment, every man can feel he like played lacrosse at Dartmouth. Wherever you go, you will find good old-fashioned obsequious hotel service.
It’s all insistently civilized. No loud voices, beyond the occasional hearty country club laugh. Every 10-year-old knows to shake your hand firmly upon meeting you. Not once did I see someone texting while walking, or children with phones at a meal — they talked to their parents. And all of this happens without formal rules beyond a rudimentary dress code.
Perhaps the biggest unwritten rule of all here is discretion, and the sense of an insider feel it lends the hotel. The pro shop sells baseball caps with the Gasparilla Inn’s pirate logo, but not its name.