Best 199 things to do in Anna Maria, FL

Cruise Madeira Beach for 2 hours on a tiki boat at sunset

Rent an adult bike and ride Gulf Blvd. for 4 hours to 7 days

Rent a paddle board in Madeira Beach for 2–8 hours

Get out on the water with flexible 2–8 hour kayak rentals

Get on the water with flexible 2–8 hour paddle board rentals

Ride a 13-mile historic railroad excursion in open-air or air-conditioned cars.

Visit the gift shop and model railroad display in Parrish

Take the controls of a locomotive for an hour

Cruise Siesta Key by e-bike with a rental timed for sunset

Stretch, unwind, and rejuvenate—right in the comfort of your vacation rental.

Explore pristine sandbars, collect shells, and relax on a fun 3-hour boat excursion

Cruise Sarasota Bay at sunset and look for dolphins

Cruise Anna Maria Island waterways and look for dolphins with drinks included

Cruise Sarasota Bay at sunset and look for dolphins

Cruise the bay with gourmet donuts and wildlife spotting

Cruise Sarasota Bay for dolphin sightings with donuts and coffee

Cruise the Intracoastal Waterway with dolphin and manatee spotting

Charter a private boat for your group from Anna Maria Island

Charter a private FunBoat on Anna Maria Island with paddleboards and beach games

Charter the FunBoat with crew, paddleboards, and beach games

Private boat charter for up to 20 with paddleboards, beach games, and crew

Charter a FunBoat with paddleboards and beach games for your group

Watch playful dolphins and a vibrant Gulf sunset while enjoying complimentary beer and wine.

Enjoy a morning cruise with complimentary drinks while spotting dolphins in Siesta Key.