Best 281 things to do in Longboat Key, FL

Cruise John’s Pass on a 90-minute pirate ship adventure

Cruise Boca Ciega Bay and learn about local dolphins with your crew

Cruise Boca Ciega Bay at sunset via John’s Pass

Fish for snapper and sea bass on a 5-hour trip close to shore from John’s Pass

Cruise John’s Pass at sunset with free beer and wine

Spend 6–7 hours fishing offshore from Madeira Beach

Cruise 70–100 miles offshore for 7–8 hours of deep-water fishing

Cruise from John’s Pass to Shell Key for island shelling

Fish offshore at night with 7–9 hours of lines-in time

Fish for trophy sharks with rod, reel, and heavy shark gear provided

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

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

Paddle a private sunset route with a dedicated guide in Sarasota Bay

Ride the latest 3-seater jet skis and enjoy hassle-free fun on the water.

Cruise with up to 13 friends on a spacious pontoon equipped for sandbar hopping