But Boca isn’t all traditional garb and afternoon tea. Rent a golf cart and follow the banyan-tree-lined streets through the diminutive downtown, and you’ll end up at a pigpen. Since 1926, the Whidden family’s namesake marina has been an epicenter of Boca Grande’s sportfishing community, dispensing bait, beer, fuel, and local gossip from a waterfront compound that has aged into a sort of shabby-chic patina. The angles of the storefront are akimbo, weathered nautical flotsam decorate the premises, and the resident swine—along with the goat that lives out by the wooden water tank and assorted waterfowl that roam the grounds— create the atmosphere of a movie set.
Sitting midway between Whidden’s and the Gasparilla Inn, both ideologically and geographically, is the Boca Grande Marina. In addition to offering the most accommodating, modern transient dockage on the island, it’s also the closest marina to downtown action. Like most points on the island, it’s just a short stroll away from the Gulf beaches.
In contrast to Boca Grande’s genteel diversions, the island just to the south offers a truly wild Florida experience. Cayo Costa is reputed to have been the haunt of the pirate José Gaspar. Later, it became Florida’s version of Ellis Island, when thousands of immigrants arriving from Caribbean ports in the 19th century were held there in quarantine. A small fishing community thrived through the 1920s, but isolation from the mainland led to abandonment, and in 1976, the entire island became a state park.
Today, park service ferries deposit small groups of day trippers on Cayo Costa’s uninhabited shores, while private vessels drawing five feet or less can ease over the entrance bar and drop the hook in the protected waters of adjacent Pelican Bay. That was stop number two on our agenda, where we enjoyed steaks on the grill at sunset and a full moon rising across the sound. The morning after, we took the tender ashore to make the half-mile crossisland stroll to a truly deserted beach.