Anna Maria Island: A Self-Guided Cycling Tour

On this self-guided 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. 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.

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   You’ll pass by the Old City Jail, a quirky historic site once used to hold minor offenders, now preserved as a reminder of the island’s early law enforcement. Any costs related to visiting the area are not covered in this tour.

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   You’ll pass by the Roser Memorial Community Church, a historic church dating back to 1913, known for its distinctive Gothic Revival architecture and community heritage. Please note that entry to the church is not included in this tour.

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   You’ll pass by the Anna Maria City Pier, a historic wooden pier stretching into Tampa Bay, known for its sweeping views and relaxed coastal atmosphere. Any costs related to visiting the area are not covered in this tour.

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   You’ll pass by the Anna Maria Motel & Resort, a laid-back beachfront property known for its classic island style and easy access to the Gulf of Mexico. Please note that entry to the property or use of its facilities is not included in this tour.

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   You’ll pass by Sandbar Seafood & Spirits, a popular beachfront restaurant known for its fresh seafood and sunset views over the Gulf of Mexico. Please note that entry to the restaurant or any purchases made inside are not included in this tour.

• Public transportation options are available nearby
• Suitable for all physical fitness levels

For a full refund, cancel at least 24 hours before the scheduled departure time.