things to do in Osprey, FL

Cruise scenic waterways with a captain and look for local dolphins

Explore Lido Key’s mangrove tunnels with included gear, map, and a brief lesson

Parasail with an 800 ft line and 14 minutes of flight time

Ride new Yamaha jet skis across Florida's largest riding area at your own pace

Rent a street-legal 6-passenger golf cart and explore Siesta Key

Ride Yamaha jet skis with fuel included on Anna Maria Island

Kayak Sarasota’s mangrove islands with an experienced guide on a 2-hour afternoon tour

An easy paddle outing for families and friends

Private coastal cruise with dolphin and wildlife viewing

Test your trivia skills from the skies over Sarasota

Cruise sandbars and island stops on your own schedule

Paddle Robinson Preserve's mangrove estuary in a clear tandem kayak

Music, dancing and a tiki bar stop as the sun sets

Paddle between Anna Maria Island and Longboat Key with a guided wildlife-focused route

Fly parasailing on a private trip for up to 12, with observer spots if space allows

Cruise Sarasota’s Gulf waters on a spacious pontoon with flexible 4- or 8-hour options.

Rent a 23-foot pontoon for up to 10 people

Electric island transport with delivery and pickup on Siesta Key

Paddle the Lido Key Mangrove Tunnels with a 4-hour single or tandem kayak rental

Private island boating with swim, snorkel, and paddleboard time

Make Egmont Key your private beach day

Paddle Lido Key’s mangrove tunnels with a guide in 2 hours

Cruise, swim, and island hop on a fully loaded pontoon

Cruise, swim, and beach-hop around Anna Maria Island aboard a spacious deck boat