What It's Like to Stay at the Most Exclusive Inn and Club in Florida

A stay at the Gasparilla Inn & Club, a grand resort on the isle of Boca Grande, is a return to the genteel world of Old Florida.

Entrance and bikes at the exclusive Gasparilla Inn, in Florida
Photo: From left: Compass + Twine; Amalie Orrange

The opening night of the social season at the Gasparilla Inn & Club is always a big deal. The date changes each year and in the days leading up to it, there’s a sense of anticipation in the air, as Mercedes station wagons and Range Rovers pull around the circular driveway to unload garment bags and golf clubs and the hotel comes to life with families — grandparents, the kids, and grandkids in tow. Many of the entourages have looked forward to this day every year for the past 10, 20, 30 years.

The big night unfolds like so: Men in Brooks Brothers clothes and women in Gretchen Scott — with a glass of Champagne in one hand and the collar of a navy-blazered child in the other — stroll through the butter-yellow halls to the dining room, where big round tables of eight and 10 are set with white linens and emerald-green goblets. Parents leap from tables as they rediscover one another — “Hey, buddy!” — while children recognize the friends they dug sandcastles with a year earlier. The delicious local grouper everybody has been looking forward to is still on the menu.

Soon enough, the season is off and running. The next morning it continues over a big breakfast (creamed chipped beef, anyone?) and a round of golf on the Pete Dye-designed course. Then it’s off to the Beach Club for a salad followed by an hour staring at the Gulf from a chaise lounge, drink in hand, before it’s time to dress for dinner. Well, maybe one quick game of Ping-Pong first. And the next day it begins all over again.

Scenes from Gasparilla Inn, in Florida
From left: Compass + Twine; Amalie Orrange

There are so many Florida resorts I have lost count. But the scene at the Gasparilla Inn & Club was a new one to me — quite unlike the setting of the Breakers resort, the center of the Palm Beach social set, and at least several million light-years from the Faena Hotel in Miami Beach, with its art and fashion crowd.

“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 cocky squillionaire who relies on “Do you know who I am?” to get his way will have a rough time of it here. 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.”

Related: The Top 10 Resort Hotels in Florida (Outside of Miami Beach)

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.

Terrace and Interior at the Gasparilla Inn, in Florida
From left: Compass + Twine; Amalie Orrange

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. No waiter here ever begins a meal by asking, “So, how are we doing tonight?”

It’s all insistently civilized. Here are some of the more astonishing things I experienced during my three-day stay: 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. You just wouldn’t dare.

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. If you take one home and wear it in the right zip code, you can count on strangers pulling you aside and saying, “Don’t you just love that place? We’ve been going for years.” Look them in the eye and say, “Oh, we just love it.” It will never occur to them that you’ve only been once.

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