Best 568 things to do in Longboat Key, FL

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

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

Fish Tampa Bay’s inshore waters with premium gear, live bait, and room for up to six anglers

Private inshore fishing for snook, redfish and more

Target Tampa Bay inshore favorites with premium gear and live bait

Pursue Tampa Bay tarpon aboard Capt. Kyle Wallace’s 25-foot C-Hawk

Private tarpon fishing with premium gear and live bait included

Celebrate on an 84-foot yacht cruising Tampa Bay or the Gulf of Mexico

Cruise Southwest Florida waters on a 2-hour public tiki boat

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

Watch the Gulf Coast sunset from the water on a pontoon cruise

Book your own private tiki boat near John’s Pass for 2, 3, or 4 hours

Cruise to Shell Key Island and Egmont Key for shelling, snorkeling, and dolphin spotting

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

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

Cruise Madeira Beach on your schedule with flexible scooter rental times

Paddle, snorkel, and float at John’s Pass sandbar

Choose your launch point with kayak delivery and pickup

Ride through Venice with scripture, music, prayer, and pink flair

Join a 1920s speakeasy dinner show and help solve the crime