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It’s no surprise that posh yet understated Boca Grande has been attracting members of the glitterati for decades. The Bushes were known to vacation here, and so was Katharine Hepburn. Tucker Carlson, Tom Brokaw and Harrison Ford have all been spotted on its pedestrian-friendly streets. But unlike other Florida enclaves for the wealthy and famous, Boca Grande is free of strut. Flip-flops are the footwear of choice. A pair of Wayfarers is practically mandatory. The draw here is exactly the kind of laidback Florida charm that has been bringing visitors to the Gulfshore for more than a century. 

World-class Sport Fishing

The tiny fishing village of Boca Grande stepped onto the national stage in the late 1800s when upper crust gentlemen discovered that the Boca Grande Pass offers some of the finest sport fishing in the world. Wealthy sportsmen from the United States and Great Britain made their way to the barrier island, intent on fishing for the mighty tarpon, a top-notch game fish. 

Today, Boca Grande Pass still offers some of the best sport fishing around. Capt. Chris Slattery of Reel Intense Inshore Charters (5800 Gasparilla Road, 941.468.1618, reelintenseinshore.com) has a reputation as an elite sport fisherman and guide. He’s won several local fishing tournaments, and his charters regularly reel in 100-pound tarpon. Capt. Andrew Herzog at Big Bully Fishing (6499 Gasparilla Road, 941.661.0304, bigbullyfishing.com) also takes his charters to just the right spot. His knowledge of local fishing is vast, and he works closely with NOAA and FWC.

A Night in the Social Register

For a weekend trip to Boca Grande, a stay at the Gasparilla Inn (500 Palm Ave., 800.996.1913, the-gasparilla-inn.com) is a must. The original hotel was built in 1911. It began as a modest structure, but was soon expanded to become a world-class resort, adding on a beach club, a golf course, tennis courts and a croquet lawn. Today, the 137-room grande dame offers guest rooms, cottages and villas outfitted with tasteful tropical décor. Take note: The inn’s dining room has a formal dress code during the winter months from December to April. Jackets are required for dinner, though ties are optional. 

Catch a Bite

Like many Florida vacation spots—even the well-heeled ones—eating out is mostly a casual affair in Boca Grande. For an easy breakfast or lunch option, visit the Loose Caboose (433 4th St. West, 941.964.0440, loosecaboose.biz). Located in the historic train depot, the Caboose is a local institution. Don’t miss Tuesday’s meatloaf night. 

The Pink Elephant (491 Bayou Ave., 941.964.4540, the-gasparilla-inn.com) is known affectionately around town as The Pink. It features popular sandwiches on its lunch menu and a seafood-focused dinner menu. Explore the pink-themed cocktail list with its fresh and fun concoctions, and especially try the Spicy Elephant, which has jalapeno tequila, triple sec, watermelon puree and fresh lime juice. With the Gasparilla Inn just a short walk away, it’s OK to indulge.  

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