Step into a sun-drenched time capsule of Old Florida glamour.

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Setting the scene

A storied yet elusive icon of American hospitality, The Gasparilla Inn presides over its namesake barrier island on Florida’s Gulf Coast, long tied to tales of the pirate Gasparilla and his hidden treasure.

You won’t find buried gold here, but you will find a 1913 landmark that has matured into a vivid portrait of Old Florida grace. The property includes a 63-room New England-style inn surrounded by yellow clapboard cottages, a Pete Dye golf course on its own island, and a sprawling Beach Club framed by palms, bougainvillaea, and banyan trees along one of the state’s finest beaches.

Reaching the island means crossing a small toll bridge and leaving the modern world behind. Once across, there are no traffic lights and no chain stores. It’s a vortex of residential side streets, shell-paved lanes, banyan canopies, and porches strung with wicker swings as the ocean sparkles to the west and the bay to the east. Golf carts replace cars, and conversation replaces noise. Guests span generations: families returning for decades, first-timers instantly taken with the place, and long-time regulars in Lily Pulitzer and resort whites. Everyone seems to know someone, and that quiet familiarity defines the experience.

The backstory

Opened in 1913, the Inn has had only three owners, each of whom has been devoted to preserving its original character. Current stewards William S Farish, former US Ambassador to the Court of St James, and his wife, Sarah, granddaughter of past owner Bayard Sharp, continue that tradition with extraordinary attention to detail.

Listed on the National Register of Historic Places and a member of Historic Hotels of America, the Inn still runs on its own schedule. It is open from October through early July, reservations are made by phone, and the optional meal plan includes breakfast, lunch, and dinner (as well as options for just breakfast or breakfast and dinner). The pirate legend lingers through subtle touches: the Gasparilla cartoon logo is embroidered on robes and totes, stickers seal bathroom tissue, and souvenirs are available in the gift shop. It is all delivered with folkloric fun rather than gimmick – and guests can’t get enough.

Condé Nast Traveller