December 7, 2022

If we let you in on a little secret, you have to promise not to tell. It’s the most underrated beach this season and it’s brimming with white sand beaches, turquoise waters and an exuberant amount of charm. Step back in time to old-world Florida, where pastel-hued cottages take the place of high rise condos. Here, time stands still and postcard-worthy memories are made.

While Gasparilla Island isn’t a newcomer to the beach scene – the Vanderbilt’s and DuPont’s have been vacationing on the island since 1913 – it still flies under the radar. It attracts mostly locals and well-heeled travelers clad in the latest Lily Pulitzer prints, looking for a little piece of paradise that still exists.

Where to Stay

Gasparilla Inn and Club

Credit: Gasparilla Inn and Club

Built in 1911, this hidden gem has gone through many re-inspirations, but still manages to maintain its’ old Florida charm. With three croquet lawns, cottages and a Pete Dye designed golf course, tennis and beach club, Gasparilla Inn and Club exudes an understated elegance.

Things to do

The island itself offers an array of activities from snorkeling to fishing. Here are a few of our favorites.

Credit: Gasparilla Inn and Club

Visit Cayo Costa State Park

Cayo Costa can only be reached by boat, but the nine miles of secluded shores and waters rich with sea life, make it worth the journey.

Fishing

Anglers head to Boca Grande Pass, known for its recreational fishing of tarpon, redfish, snook and trout.

Shelling

Winter months offer the best shells, but we can bet if you get up early and stroll the shore you’ll find a few treasures any time of year.

Port Boca Grande Lighthouse

The oldest structure on the island, Port Boca Grande Lighthouse has been a beacon to mariners since 1890. Today, the lighthouse is home to a five-room comprehensive museum covering history and culture from 12,000 BC to present.

Dining

The Pink Elephant

Credit: Gasparilla Inn and Club

The island favorite, known as “The Pink” has been serving guests for over 60 years. Chef Rob Plesh puts an imaginative flair on regional cuisine, seafood, and steaks. Located on the Boca Grande Bay Bayou at the Gasparilla Inn and Club, the venue boasts an upstairs dining room, outdoor patio, and pub on the main floor.

The Innlet

The casual breakfast and lunch hotspot, located on the Bayou delivers fresh seasonal plates such as blackened fish sandwiches, salads, and traditional breakfast fare.

Sisters restaurant

Located at the corner of 5th Street and East Railroad Avenue under the towering Banyan tree, Sisters Restaurant offers Italian cuisine created by the Chef Monty Caputo.

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