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Charming Anna Maria Island in Florida

Anna Maria Island, an incredible island in Florida, is renowned for its stunning beaches, picturesque sunsets, and cozy ambiance. Immerse yourself in a world of relaxation, culinary delights, and natural beauty of this unique destination.

Anna Maria Island is a barrier island along the Gulf of Mexico coast of Florida, about an hour's drive from Tampa Airport. Families from all over the world come here to enjoy the beaches, atmosphere, and weather.

History of Anna Maria Island

Anna Maria Island, a breathtaking Florida island, was first settled in 1893 by George Bean, who, along with his family, made their home at the island's northern end. This marked the beginning of the island's development. Shortly thereafter, George's sons began devising plans for a resort.

In 1907, a significant figure named Jack Holmes, who worked on the East Coast Railway construction, arrived on the island. His visit had a profound impact on the community. By 1911, the first brochures were created, promoting the island as a resort destination. A hotel, restaurant, bathhouse, and freshwater artesian wells with "healing properties" were constructed. To reach the island at that time, two ferry rides were required, and from Tampa, it took a day. By 1922, the first bridge was built from the fishing village of Cortez, and in 1926, another bridge connected Anna Maria to the town of Longboat Key.

By 1934, Jack Holmes returned to Anna Maria Island to reside permanently. He managed private residences and collected rental payments. After World War II, Jack acquired 350 acres of land to develop the Holmes Beach beachfront community. By 1951, Holmes Beach had evolved into a full-fledged town, with 180 homes built within a year.

The rapid development pace continued through the 1950s and 1960s. By 1965, Holmes Beach had a population of 3,000 residents.

Photo of the beach on the island of Anna Maria in Florida — American Butler

Things to do on the island

  • Biking Around the Island
    The best way to explore Anna Maria Island in all its glory. Quiet neighborhoods, immaculate landscaping, and massive majestic trees immerse you in the island's slow pace of life. Due to the tourist influx, on some days, you can get from one side of the island to the other faster on a bike than by car. Another great alternative is to rent a golf cart.
  • Strolling on the Beach at Night
    Walking on the beach at night is as astonishing as during the day. With very little city light on Anna Maria Island, you can clearly see the starry sky at night. Bring a blanket or towel, get comfortable, and look for constellations you never knew existed.
  • Dining at Rod and Reel with a Pier View
    Dining outside on the porch of Rod and Reel, you might see dolphins, stingrays, and schools of fish. As for the food, the restaurant is intriguing, offering dishes like a giant fillet of fresh grouper cooked to your liking on a toasted bun, served with a side and clam chowder. This crowded place is popular among tourists and locals, so expect to queue. Don't like waiting? Visit during off-peak hours for a better experience.
  • Shopping on Pine Avenue
    What you’ll find: Olive Oil Outpost sells olive oils, spices, and gourmet cheeses. At the Pink and Navy clothing store, you'll find both new and pre-owned wardrobe items. What you won’t find: low-quality tourist shops filled with tasteless beach outfits or kitschy souvenirs.
  • Exploring Bean Point
    What is Bean Point, you ask? It's the northernmost part of Anna Maria, where the Gulf of Mexico meets Tampa Bay, and the viewing platform offers views of endless miles of turquoise waters.
  • Photographing at Old Anna Maria Jail
    The old city jail was used as a place for islanders who had too much to drink at the local tavern to sober up. A fire in the 1940s destroyed the wooden roof, so it's no longer in use, but the rest of the structure remains.
  • Guessing Sunset Time at Sandbar Restaurant
    A fun way to add a bit of friendly competition to your trip. Each evening, the restaurant hosts a contest to guess the exact time of sunset. The winner gets a bottle of champagne.
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Anna Maria Island is a beach paradise in Florida, a place where everyone can find something special. It combines unique natural beauty, cozy cafes and restaurants, and numerous opportunities for active recreation. From serene moments on golden sands to exploring rich marine life through snorkeling and kayaking, Anna Maria Island offers a variety of ways to enjoy life.

For those who want to make the most of their stay on the island, American Butler offers comprehensive trip planning services. We'll help you plan the perfect vacation, from booking the best accommodations to organizing tours and activities. With us, you can expect a carefree vacation and full immersion in the atmosphere of this unique place.

Discover all the delights of Anna Maria Island with American Butler — your reliable partner in travels around Florida!

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