Is­land tales tell of past and present char­ac­ters

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The Heart of Cap­tiva

Cap­tiva Is­land emerged out of a spit of sand. Plants have held the shift­ing sand in place for hun­dreds of years, but it is the peo­ple—artists, fish­er­men, farm­ers, boot­leg­gers, writ­ers, World War I me­chan­ics, guides, and ho­tel pro­pri­etors—who truly have kept the is­land to­gether, tide af­ter tide.

The heart of ev­ery is­land is where peo­ple gather. In decades past, the gath­er­ing spot on Cap­tiva Is­land was the City Dock, which is now known as McCarthy’s Ma­rina. Long be­fore the cause­way, all com­merce would come to the City Dock by boat. And at noon, the mail boat would pull in with the news of the day.

Back in the early 1930s, the City Dock and Ma­rina were owned by Pops Ran­dall. Be­fore Ran­dall passed away in the late 1930s, his wife wanted a fish­ing guide by the name of Andy Rosse to buy the dock and ma­rina. As the story goes, Rosse asked his friend Jay Nor­wood “Ding” Dar­ling for the $800 to be able to make the pur­chase, and Dar­ling loaned him the money that same day.

Andy Rosse—for whom the is­land’s Andy Rosse Lane is named—was a com­mer­cial fish­er­man through­out most of his life un­til 1935, when he be­came a guide at ’Tween Waters Inn. Af­ter guid­ing for a few years, Rosse then bought the City Dock and Ma­rina and re­named it Andy’s Fish­ing Pier.

It was known lo­cally as Andy’s Dock. Over the years, Andy’s Dock be­came quite the so­cial gath­er­ing place. Satur­days were al­ways lively. Fish­er­men would bring their catch in at noon and the party would last all night—with Rosse play­ing his gui­tar and en­ter­tain­ing guests into the wee hours of the morn­ing. Artists have al­ways been a big part of Cap­tiva, too. Rosse’s friend “Ding” Dar­ling was a well-known po­lit­i­cal car­toon­ist from Des Moines, Iowa. The two-time Pulitzer Prize win­ner also started the Fed­eral Duck Stamp pro­gram. Dar­ling was an in­te­gral part of the Cap­tiva com­mu­nity. In ad­di­tion to lend­ing money, the artist owned a gro­cery store on the is­land and had a stilt house over the wa­ter that is still a pop­u­lar land­mark to­day.

Dar­ling’s fa­vorite fish­ing guide was Capt. Bel­ton Johnson. He was a pop­u­lar guide who was known for his “abil­ity” to bring whiskey from Sani­bel over to Cap­tiva. Johnson was well schooled in the waters of South­west Florida and cap­tained a 75-foot yacht named the Wani­gan for its owner, a woman named Alice O’Brien.

O’Brien was orig­i­nally from Min­nesota. She first came to Cap­tiva in the 1930s and pur­chased prop­erty to the south of ’Tween Waters Inn. A seawall was built for her yacht, along with a house and cot­tages.

Johnson cap­tained the Wani­gan on many ex­cur­sions along the West Coast of Florida as far as the Shark River in Mon­roe

County, and across the mid­dle of the state through Lake Okee­chobee to the East Coast. O’Brien was known not only for be­ing an avid boater and for her gen­eros­ity, but also for hav­ing been a me­chanic in World War I.

The more things change on this 5-mile spit of sand, the more they stay the same. If you look close enough on Andy Rosse Lane—pos­si­bly by peer­ing be­tween the palms—you just may see some artists talk­ing at the Is­land Store, or a few fish­er­men con­vers­ing with lo­cal writ­ers. Or per­haps a cou­ple of strangers may be re­mark­ing at McCarthy’s Ma­rina about the “char­ac­ters” on Cap­tiva. No one is an is­land to them­selves. Capt. Brian Ho­l­away is a Florida master nat­u­ral­ist and has been a South­west Florida shelling and eco-tour guide since 1995. His char­ters visit the is­lands of Pine Is­land Sound, in­clud­ing Cayo Costa State Park, Cab­bage Key, Pine Is­land and North Cap­tiva.

To­day Cap­tiva’s down­town dock is known as McCarthy’s Ma­rina; vin­tage post­cards show the is­land’s his­toric mail boat, and Andy’s Dock.

McCarthy’s Ma­rina and the Is­land Store (be­low) on Andy Rosse Lane are al­most as fa­mous as Cap­tiva’s beaches.

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