Best 781 things to do in Anna Maria, FL

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

Cruise Madeira Beach waterways with a captain as the sun sets

Cruise Madeira Beach waters near John's Pass on a spacious pontoon

Captain-led pontoon time for your own day on the water

Shell, snorkel and look for wildlife on a captained Gulf Coast cruise

Enjoy flexible 2–8 hour rentals to get on the water

Bring your crew aboard for a Gulf Coast sunset cruise

Private 2-hour sunset sail with downtown St. Petersburg views

Relax on a 3-hour sail with a U.S. Coast Guard–licensed captain from downtown St. Pete

Start the day aboard a classic yacht with optional sailing instruction

Relax across four social spaces on a private Sarasota Bay catamaran

Sail into golden hour aboard a private 48-foot Jeanneau yacht

Cruise Tampa Bay at sunset with flybridge views and space to unwind

Design your own Tampa Bay day aboard a spacious power catamaran

Private catamaran sailing with space to swim, paddle, and unwind

Sail Tampa Bay on a spacious catamaran with room to relax and swim

Sail Tampa Bay at golden hour aboard a 40-foot luxury catamaran

Private, wind-driven sailing aboard a 48-foot Jeanneau yacht

Cruise aboard a Galeon yacht with fold-out beach decks and water toys

Cruise Tampa Bay aboard a spacious power catamaran with room to relax and gather

Cruise into golden hour with beach decks, a flybridge lounge, and space to celebrate

Sail Tampa Bay aboard a private 48-foot Jeanneau yacht

Book a 3- or 4-hour private sunset cruise on a 38-foot Sea Ray

Sunset jet ski ride with fast Gulf access from Siesta Key