Anna Maria Island is an exceptional destination for year-round sun and fun. Fall and winter are mild and dry, perfect for exploring the island's Old Florida Charm. Spring break season is surprisingly family-friendly, and for mild weather and manageable crowds, April and May are hard to beat. Summer is the peak season for vacationing families. Fall and winter are slower, though New Year's Eve is an extremely popular holiday here.

Most visitors fly into Sarasota-Bradenton International Airport, about 30 minutes away. Tampa International is roughly an hour north. If you plan to stay on AMI itself, renting a car isn’t really needed as you can reach AMI from the airport via rideshare or private car service.

You do not need a car to enjoy Anna Maria Island. The island itself is only seven miles long, making it easy to walk or bike to many attractions. There is also a free island trolley, and ride-share services are easily accessible. Many visitors rent golf carts or bikes to get around the island. It’s worth keeping in mind that having a car can help with off-island trips.

• New Year's Eve is one of the island’s biggest events, with fireworks, beach gatherings, and live entertainment.
• In March, a two-day fine arts festival known as Springfest draws crowds, as well as the annual St. Patrick’s Day Parade.
• July 4th is another popular holiday, with the island's small town charm providing the perfect backdrop to family-friendly fun.
• Fall fun includes Bayfest in October, live symphonic music at Symphony on the Sand and pumpkin picking and hay rides at Hunsader Farms' fall festival.