Here’s a secret about Anna Maria Island: The destination is just as fantastic in the shoulder season as during the summer. With cooler temperatures and less humidity, many visitors find it their favorite time of year on AMI. 

If you think winter means less to do, think again. There are plenty of activities and experiences to keep you busy this time of year. 

Visit the beach. The weather stays warm enough – in the 70s – to enjoy our beaches, which are far less crowded than in spring and summer. While it’s not the season for staying in the water (unless you are wearing a wetsuit), the weather is perfect for beach combing, sunbathing, flying a kite, or reading a book. Rent a beach set-up from our partner, CabanUp

Farmers Markets make a marvelous way to spend time. Discover an array of local produce, artwork, and mouthwatering food. The Bridge Street Market, 107 Bridge St. in Bradenton Beach, runs from 10 a.m. to 3 p.m. every Sunday through April. The Coquina Beach Market, 2650 Gulf Drive South in Bradenton Beach, is open from 10 a.m. to 4 p.m. Sundays and Wednesdays.

Spend a day strolling Pine Avenue in Anna Maria for shopping and dining. Pop into Anna Maria Olive Oil Outpost, 401 Pine Ave., for meticulously crafted extra virgin olive oils in various flavors. Shop at boutiques such as Pineapple MarketplaceThe Island CabanaShiny Fish Emporium and more. 

Take a pic at the Old City Jail, part of the AMI Historical Society Complex at 402 Pine Ave. The museum is open 10 a.m. to 4 p.m., Tuesday through Saturday. The jail dates to 1927, and housed rowdies who had too much to drink until the 1940s, when it caught fire. The wooden roof burned away, but the original tabby structure remains. The jail is one of the most photographed attractions on the Island. Admission to the museum is free, though donations are accepted. 

Travel AMI like a local with a golf cart rental. Beach Bums AMI rents street-legal electric carts, which makes a great way to get around AMI. And riding around in a golf cart is a fun adventure. Rent by the day, week, or month. 

Talk about a fun way to get around AMI, Beach Bums AMI also rents bicycles. With flat terrain, bicycling is an easy-breezy way to see the sights, and get to the stores and restaurants. Beach Bums AMI even rents tandem bikes and adult-size tricycles. They offer free delivery to your vacation rental

Open 365 days a year, Robinson Preserve in northwest Bradenton offers more than 680 acres with hiking trails, canoe launches, bicycle trails, picnic areas and more. The park is open sunrise to sunset.

Book a winter stay to enjoy one of the best seasons on Anna Maria Island.