Ahh, September in the Gulf of Mexico. The crowds of the summer months have begun to depart, and the snowbirds won't arrive for a couple of months. September, the start of the autumn shoulder season in Florida, is one of the best times of the year to visit Anna Maria Island (AMI). Due in part to its comfortable climate, fewer crowds, and a wide array of things to do, an Anna Maria Island getaway in September is always a good idea.
Read MoreCategory: Seasonal + Events
Anna Maria Island in September: What to Expect (2026)
Symphony on the Sand (2026): What to Expect
Symphony on the Sand is a lovely annual event that pairs a beachfront concert with dinner from some of the island's favorite restaurants. Lovers of music, beaches, and Anna Maria Island revel in the beauty of one of the most anticipated nights on AMI.
Read MoreAnna Maria Island in August: What to Expect (2026)
Anna Maria Island is a true gem on Florida's Gulf Coast, offering visitors a perfect blend of natural beauty, warm weather, and a relaxed island vibe. Our vacation rentals will help you thoroughly enjoy the laid-back charm and spectacular beaches of this Florida mainstay.
Read MoreAnna Maria Island in June: What to Expect (2026)
Why Visit Anna Maria Island in June? Imagine fourteen hours of sun-soaked days, warm Gulf breezes caressing sugar-white sands, and the vibrant energy of a Florida summer just beginning to bloom.
Read MoreMemorial Day Weekend on Anna Maria Island (2026)
Wondering how to best spend Memorial Day weekend on Anna Maria Island? From enjoying Memorial Day parades to relaxing on pristine beaches, this guide highlights the top activities and events that make the holiday special.
Read MoreMay on Anna Maria Island: What to Expect (2026)
Anna Maria Island is a hidden gem on Florida's Gulf Coast, renowned for its laid-back charm, breathtaking turquoise waters, and pristine sandy beaches. May marks the sweet spot between spring's dry stretch and the busiest season in the summer heat, making it the perfect time for a visit.
Read MoreApril on Anna Maria Island: What to Expect (2026)
April is one of the best times to experience Anna Maria Island. The crowds have thinned from spring break, the weather is warm but not sweltering, and the island hums with just the right amount of energy from seasonal festivals and outdoor adventures.
Read MoreA Visitor’s Guide to Spring on Anna Maria Island (2026)
Anna Maria Island, a picturesque barrier island on Florida's Gulf Coast, is a popular year-round destination known for its sandy expanses of shoreline, clear waters, and welcoming atmosphere
Read MoreMarch on Anna Maria Island: What to Expect (2026)
If you're looking for the perfect spring getaway, Anna Maria Island in March offers just that. Imagine walking along seven miles of pristine beaches, with warm sand underfoot and the Gulf of Mexico stretching before you.
Read MoreFebruary on Anna Maria Island: What to Expect (2026)
While much of the country shivers through winter, February on Anna Maria Island (AMI) offers a warm escape with perfect weather and uncrowded beaches.
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