Best Historic Stays: The Gasparilla Inn & Club
Now in its 112th season, The Gasparilla Inn in Boca Grande on Gasparilla Island still feels like a hidden treasure. The “Grand Dame” of this quiet barrier island continues to hold onto its timeless charm while making a lasting imprint on the community.
History of The Gasparilla Inn
The property first opened in 1911 as The Hotel Boca Grande, a 20-room escape designed to be a peaceful, exclusive retreat. Just two years later in 1913, the hotel expanded and was renamed The Gasparilla Inn in honor of 19th-century pirate legend José Gaspar.
The inn quickly became a favorite for elite travelers. J.P. Morgan, Henry DuPont, Harvey Firestone, artists, and well-known families made it their getaway of choice.
In 1930, Barron Collier, the namesake of Collier County, purchased the property and added signature touches, from the grand Neo-Classical façade and sweeping verandas to a collection of guest cottages. He also introduced The Pelican Room, a private space for the resort’s fishing club.
The Gasparilla Inn joined Historic Hotels of America in 2007 and earned a spot on the National Register of Historic Places in 2008. And, in 2025 it was named the number one resort in Florida by the readers of Travel + Leisure.
Staying at The Gasparilla Inn Today
Remarkably, the inn has only had three family owners in more than a century. Today, it remains a cherished tradition for generations of legacy guests.
You feel the history immediately as you step between the white columns, across the polished porch, and into Florida’s oldest wooden hotel. The comforting creaks in the hallway and guest rooms add to its charm.
Inside, you'll find whimsical Florida-maximalist décor with vintage touches, vibrant patterns, and restored pieces everywhere you look.
I stayed in a Junior Suite (Room 323) overlooking the championship golf course with fantastic sunrise views. For extra privacy and additional luxury, guests can choose from cottages, villas, and private homes.
The inn is open October to July, using the off-season to carefully preserve the historic property and prepare for fall.
Amenities at The Gasparilla Inn
The Inn’s footprint on Boca Grande is impressive. Guests can enjoy a 7,000-yard championship golf course, a 250-slip marina, clay tennis and pickleball courts, croquet lawns, and more.
The Beach Club is the standout with three pools, shaded lounge areas, seaside dining, and turquoise Gulf waters right at your doorstep.
Dining at The Gasparilla Inn
Dining here is an experience. The Main Dining Room serves breakfast and dinner in an elegant, candlelit setting. I especially loved the Day Boat Scallops with sunchoke, pomegranate, and chive.
For something casual, The Pink Elephant (affectionately called “The Pink”) is just a short walk away and has been serving coastal favorites and signature cocktails for decades.
There’s also a casual off-site bakery offering pastries and grab-and-go bites, which is the perfect fuel before a day of exploring Boca Grande.
This trip was sponsored by the Lee County Visitor & Convention Bureau. Discover more ways to explore Southwest Florida at VisitFortMyers.com.
