Anna Maria

About Anna Maria

Anna Maria Island is a quaint Barrier Island nestled in the Gulf of Mexico. Beautiful turquoise waters and white sandy beaches are the main attraction here. It is a place where "old" Florida charm can still be found, flip flops are a way of life and the speed limit never exceeds 35mph. High rise condos and fast food restaurants are pleasantly absent from our pristine "get away from it all" island. Our accommodations and restaurants offer something for everyone. From quaint cottages by the sea to deluxe suites, from million-dollar villas to rustic cottages to own, One visit to Anna Maria Island and you will be calling it, "My island in the sun".

A Bit of History - Old World Living & Old Florida Charm

Island Inhabitants
The island was originally used for hunting and fishing by various Indian tribes and the only way on and off the island was by boat. Visit the Anna Maria Island Historical Society for a look at this island paradise in its original form when it was discovered by the local Timucan and Caloosan American Indian tribes and then by Spanish explorers (including Hernando DeSoto) in the name of the Spanish Crown.

In 1892 George Emerson Bean became the first permanent resident on the Island, followed by John Roser. Bean settled on the northern tip of the island, now known as Bean Point. It was Bean, his son Will along with Charles Roser who developed the area by adding streets, a water system and homes. Shortly after came a school and churches which lead to the beginning of an island community. A jail was built in 1927 for the drunk and disorderly visitors which is still standing today on Pine Avenue without a roof due to a fire in the 1940's. Mr. Bean homesteaded much of what is now the City of Anna Maria. In the early 1900s, Bean began to develop the Island with the Anna Maria Beach Company, which laid out streets, built sidewalks and houses and installed a water system.

The Gulf Drive Café was established in 1981 and has been a staple on Anna Maria Island for locals and tourists ever since. The current owners, George & Wendy Kokolis, purchased the historic property in 1987. The Kokolis' extensive experience in the restaurant industry has expanded over 45 years. After celebrating over 20 years as owners, they decided to renovate and expand the Café into a bar, The Kokonut Hut and event space, The Sunset by Gulf Drive Café. The property sits on 450 square feet of waterfront on the Gulf of Mexico and has many offerings for guests to enjoy. It includes delicious meals, impeccable service, cold cocktails, live entertainment and also kayak and paddleboard rentals from a local vendor. Directly in front of the business exists an underwater archeological preserve sight and famous diving spot. Local and visiting divers submerge themselves to catch a glimse of The Regina, a Sugar barge that sank in 1940, carrying more than 300,000 gallons of molasses from Havana, Cuba.

About Anna Maria Island

The Island's quaint simplicity and culture of sun and relaxation is a quintessential paradise getaway. Offering a diverse array of award-winning restaurants, boutiques and pristine beaches, this seven-mile stretch of history is one of Florida's best-kept secrets. A barrier island located in Manatee County, Anna Maria was first settled by the Timucan and Caloosan American Indians tribes and explored by the Spanish in 1530. It is comprised of three cities established in the 1900s: Anna Maria, Holmes Beach and Bradenton Beach. The island maintains much of the small town charm of the 20th century and is connected to mainland Bradenton by two drawbridges and to the northern end of Longboat Key. Anna Maria also preserves Cortez, one of the last remaining fishing villages on Florida's southwest Gulf Coast. On the island, you can still experience the timelessness reminiscent of Old Florida.

For live video feed of Anna Maria please visit

For more information on Holmes Beach visit

Area Listings

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Updated: 17th June, 2019 8:59 PM.

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