Anna Maria Island Stories: Movies, Mosquito Jails and Fig Newtons

Anna Maria Island feels like one of Florida’s best-kept secrets. But its peaceful beaches and laid-back culture hide a history far stranger than most visitors imagine.

On this bicycle tour, you’ll discover how an unlikely cast of characters – from a Fig Newton millionaire, to platform divers who dodged sharks – transformed a barrier island into a beloved community.

The tour starts at the Anna Maria Historical Society Museum on Pine Avenue. You’ll encounter the island’s famous “mosquito jail” – a 1927 lockup with barred windows but no glass, where biting insects proved more effective than bars at deterring crime. You’ll pedal past the Roser Memorial Church, built by Charles Roser, who created the Fig Newton cookie and the process to make it then sold his creation Nabisco for a million dollars in 1890

Along the way, you’ll learn about the making of Hollywood’s 1948 film On an Island With You, and explore Bean Point where the island’s first homesteader settled in 1892. You’ll also ride past sites devastated by 2024’s hurricanes and discover how this community of 1,000 residents rallied to rebuild.

The tour ends back at the Anna Maria Historical Museum, where you can photograph the mosquito jail and explore Belle Haven Cottage, which tumbled into the water in 1926.

On this 45-minute tour, you’ll have a chance to:

• Ride past Bimini Bay Marina, rebuilt by the Galati family which took a tornado ravaged marina and built it into a world-respected yacht company
• Hear stories of Betty Phelps, who performed diving exhibitions from a floating tower always wary of sharks who sometimes circled below
• Discover why one homeowner secretly scattered rare seashells from around the world on the beach each night for tourists to find
• See where Frank Cavendish caught a 17-foot, 1,400-pound shark in 1973 using a manta ray as bait
• Hear how eccentric Miss Eddy canceled city bonds during the Depression in exchange for marshy property
• Learn about the site where Civil War ships crashed during a storm – a disaster that was kept secret to avoid demoralizing Union troops
• Find out why this 7-mile island is divided into three separate cities by a 49-12 vote

Whether you’re a history buff, a curious traveler, or simply looking for a scenic ride, this tour offers a mix of humor and heritage – all set against the backdrop of Anna Maria’s sun‑soaked streets and Gulf breezes.