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Times of the Islands Magazine

The Heart of Captiva: Island Tales Tell of Past and Present ‘Characters’

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.

Today Captiva’s downtown dock is known as McCarthy’s Marina.

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. Fisherman 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.

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

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.

Vintage postcards show Santiva, the island’s historic mail boat, and Andy’s Dock.

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.