The 'Jewel Of Florida's Gulf Coast' Is An Island Resort Blending Historic Charm With Top-Rated Prestige

Florida is one of America's top vacation destinations, drawing visitors to world-famous Orlando attractions like Walt Disney World and swanky seaside stays in hotspots like Miami and Palm Beach, renowned for their turquoise beaches fringed with sugary sand and dotted with beach resorts. While there's no shortage of incredible hotels strung across mainland Florida's bustling beaches, on idyllic Gasparilla Island, one of the Sunshine State's 200 barrier islands, a more serene and upscale coastal getaway awaits at The Gasparilla Inn. The celebrated "jewel of Florida's Gulf Coast," this coveted escape boasts historic charm, a prestigious pedigree, and exceptional recreation and amenities.

Nestled in the exclusive community of Boca Grande, The Gasparilla Inn, with sweeping verandas and mix of Queen Anne and Neoclassical architecture, exudes "Old Florida" charm. The resort, originally known as The Hotel Boca Grande, opened in 1911 with 20 rooms. By 1913, the property had undergone the first of several expansions and reopened as The Gasparilla Inn.

In the 1960s, the resort was snapped up by Bayard Sharp, a duPont family heir and friend of former President George Bush, a frequent Gasparilla Inn guest. During his 60 years of ownership, Sharp significantly transformed the property, expanding the number of rooms and detached cottages, completely rebuilding the resort's fabled beach club, and adding luxurious amenities like a dining pavilion, lap pool, spa, and tennis clubhouse. Today, The Gasparilla Inn sprawls across 180-acres and boasts 163 rooms and 33 suites. It's registered with Historic Hotels of America and on the National Register of Historic Places.

With its privileged island location and multi-million dollar mansions, the chic Florida beach town of Boca Grande has long been a favorite of the rich and famous. Movie stars like Michael Keaton, Robert Redford, and Katherine Hepburn have all been spotted on the island, with the Gasparilla Inn being a particular VIP magnet. From the resort's inception, the creme de la creme of the American aristocracy were drawn to winter here, including the likes of J.P. Morgan, Henry DuPont, and Harvey Firestone. The salubrious weather and privacy have continued to ensure its guest list is read like a "who's who" ever since. Thomas Edison, Henry Ford, and Harrison Ford have all checked-in to this exclusive Gulf Coast retreat.

Adding to the iconic resort's hefty star power are serious traveler accolades. Readers of travel magazine Travel + Leisure voted The Gasparilla Inn the "No. 1 Resort in Florida," and it won Conde Nast Traveler's "Reader's Choice Awards" several years in a row.

Regularly booked a year in advance,  The Gasparilla Inn is the sort of destination guests return to again and again. "We have been going to the Gasparilla Inn on and off for over 40 years. It is a place that retains its history, sense of tradition, and supreme hospitality throughout every visit," gushed one Tripadvisor reviewer. Guests are fans of the resort's timeless elegance, as reflected in things like its dress code, jaunty interiors, and Southern hospitality, which invoke the luxury and nostalgia of America's first grand hotels.

Alongside historic charms and elite pedigree, guests flock to The Gasparilla Inn for colorful, upscale stays amid fabulous amenities. Elegant guest rooms and suites fill the resort's main building, while the property's lush landscape is dotted with a mix of pretty yellow cottages, open-floor-plan villas, three- and four-bedroom homes, and private oceanfront estates boasting gourmet kitchens and indoor/outdoor living. At the time of writing, rates for a Standard Guest Room start at $470 per night, but prices change significantly depending on the season.

At the Beach Club, bask in the Florida sunshine on loungers surrounding three pools, or along the powdery sands of the Gulf Coast shoreline. The Beach Club is also home to an airy dining pavilion and a spa decked out with treatment rooms. Evening jackets are required for feasting on Prime Ribeye and fresh seafood at The Main Dining Room, the fine-dining establishment. For more casual vibes, The Pink Elephant serves up "comfort food with a coastal kick" and signature top-shelf cocktails.

Recreation here is serious business. There's a beachside, 18-hole, Pete Dye-designed championship golf course, seven tennis courts, two pickleball courts, and three impeccably-manicured lawns hosting croquet. Bicycles, kayaks, paddle boards, skim boards, and snorkeling equipment are available to rent. Too strenuous? Rent a golf cart to zip around paradise all day. The Gasparilla Inn's sandwiched between Fort Meyers and the seaside retirement gem with white sands and a world-class aquarium of Sarasota. Both cities are home to international airports roughly an hour and thirty minutes from The Gasparilla Inn. Alternatively, Tampa International Airport, America's best airport for travel and food, is just over two hours away.