The Gasparilla Inn

Why book?

To step into a sun-drenched time capsule of Old Florida glamour, where meticulously maintained, century-old structures and traditions meet an exuberant mix of coastal maximalism and island whimsy. The Gasparilla Inn is more than just lodging; it’s a living legacy of hospitality that has remained perfect through the decades.

Set 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.

The rooms

A living heirloom of American resort culture, The Gasparilla Inn remains perfectly maintained, where every design detail feels correct and everything gleams. Palm Beach design house Kemble Interiors, led by Celerie Kemble and Mimi McMakin (both of whom personally worked on the Inn’s design), fills the spaces with confident colour and texture, each more lovingly composed than the next. Citrus shades, seashell mirrors, rattan furniture, and hand-painted flourishes create a kaleidoscope of cheerful patterns and textures. Overall, the look strikes a balance between nostalgia and polish, much like The Greenbrier viewed through a Palm Beach lens.

Each room tells its own story: the pink-hued ladies’ sitting room, the Main Hall dressed in avocado hues blooming with fresh orchids, and the coral-and-cream ocean cottages overlooking the Gulf. Inside the Main Inn, enter a time bygone with banistered staircases, bird prints, and cabinets of curiosities. Sixty-three rooms feature alternating colour patterns among a carousel of pastels, each exuding an Old Florida elegance and a sense of place. While everything feels quite statement-making, to be fair, bathrooms strike as rather plain and uninspiring (but spotless).

I stayed in a Veranda Suite, one of four speciality suites within the Inn. It’s located on the third (and top) story of the Inn with panoramic views of the island from three sides. The living room (which I dubbed “orange theory”) comes to life with hand-painted wallpaper depicting orange trees, complemented by throw pillows with dangling oranges and furnishings in blue and neutrals to tone down the citrusy affair. Sounds like a lot – but it works. The bedroom then transitions to an amalgam of aquas and greens, anchored by a 3D-printed headboard featuring mounting bubbles.

Newer Ocean Cottages (and the most popular accommodations) include kitchens, laundry, Gulf-front porches, and multiple bedrooms, each with a distinct personality and colour pattern. The Sharpe Houses, Cottages and Inn Villas continue the Old Florida aesthetic with wicker, shutters, and shaded verandas.

Food and drink

Dinner follows tradition rather than trend. In the Main Dining Room, jackets are required from December through March at supper time. Guests dine beneath some of the inn’s original chandeliers and repurposed furnishings, enjoying seasonal, multi-course menus that showcase gastronomic excellence. Highlights from a recent dinner included Maple Leaf Farms duck confit with celeriac, mustard, and chervil; tripletail over caponata and pine nuts; and a fig tart with almond mousse, white chocolate chantilly, and honey yoghurt sorbet for dessert. Breakfasts are also enjoyed in the Main Dining Room (but don’t worry, you don’t have to dress up in the morning) or at The Inn’s small coffee shop in “downtown” along Park Avenue.

During the day, The Beach Club serves grilled fish and bright salads beside the sparkling blue water. Meanwhile, The Pink Elephant, located near the Inn’s eastern reaches along its “bayou,” offers a mixology-forward drink menu plus an international food menu that includes a Thai twist of Florida seafood alongside Mediterranean remixes (We recommend the tuna nachos with spicy Thai chilli sauce to start and the bucatini with lobster meatballs as a main).

The spa

With seven treatment rooms and a spa pool, The Gasparilla Inn Spa is located within The Beach Club. Treatments favour skill over novelty, focusing on classic massages, facials, and scrubs. The boutique, stocked with the Inn’s coveted robes and accessories, makes a worthy final stop. At press time, plans are underway to renovate or replace the current spa complex within the next two years.

The neighborhood

Boca Grande, the town on Gasparilla Island on which the Gasparilla Inn lies, feels like a page from another era. Its compact village has one main street, Park Ave., lined with boutiques and ice-cream counters, and a 1890 lighthouse that anchors the shore. Guests spend mornings collecting shells at Gasparilla Island State Park, hiring captains to fish the tarpon-rich waters, or pedalling beneath banyan trees and pastel cottages.

Back at the Inn – which actually comprises most of the neighbourhood – days pass at The Beach Club over a design-driven expanse with three swimming pools, a restaurant, plus the beach itself. There’s also croquet happening on the Mallet Club lawns, matches at the Tennis Club, and tee time on the Pete Dye-designed, par-72, 7040-yard course (located on its own island accessible by a short bridge).

The service

Service matches the setting: attentive, practised, and genuine. Staff seem to anticipate guests’ needs before they are articulated. Greetings are warm rather than formal. Many employees have been here for decades and welcome returning families by name. It is a culture built on consistency, not performance.

For families

The Inn works for families because it feels safe, spacious, and unhurried. Yes, there’s a playground, but most children play at The Beach Club pools while grandparents watch from their loungers. Croquet and golf become shared rituals, while tennis clinics, pickleball, and kids’ programs provide variety. Large cottages and villas give everyone space without losing connection.

Eco effort

The golf course maintains Certified Green status and uses desalinated water for irrigation. Shell-paved parking lots limit runoff, and most transport happens by golf cart, bicycle, or foot.

Accessibility

Historic bones bring a few limits, but accessibility has improved. Ramps connect the main buildings, and several rooms in the Inn have been adapted. Staff are proactive in assisting guests with mobility needs.

Anything left to mention?

Pack resort whites for croquet. It’s requisite (and you’ll also want to consult the attire guide to make sure you blend in at the various on-property venues). Also, plan to expand your suitcase with the Inn’s pirate-branded gear, which is sold only on-site.