Best 469 things to do in Osprey, FL

Fly a private helicopter tour from Sarasota for up to 3 passengers

Test your trivia skills from the skies over Sarasota

Paddle to sandbars and a secluded beach for Gulf sunset views

Paddle Sarasota Bay’s mangrove tunnels and look for seasonal birdlife

Paddle mangrove tunnels and explore sandbars in Terra Ceia Bay

Cast for snapper, grouper, sharks and more on a private fishing trip

Cruise sandbars and island stops on your own schedule

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

Speed, sightseeing, and flexible time on the water

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

Fly solo, double, or triple on a parasail flight

Cruise, fish, shell, or picnic aboard a 90HP pontoon

Cruise Lemon Bay and stop at Stump Pass on a family-friendly pontoon

Fish and cruise Lemon Bay’s backwaters aboard a 50HP skiff

A fishing-ready center console for bridges and beaches around Manasota Key

Cruise Manasota Key with shade, storage and Bluetooth sound

Rent a kayak or paddleboard for 4 hours with gear, route map, and lesson

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

Paddle Longboat Pass for 4 hours with a map and basic lesson

Paddle Lido Key’s mangrove tunnels with a local naturalist guide

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

Paddle the waters between Anna Maria Island and Longboat Key with your own private guide

Toast the sunset on a guided Gulf Coast kayak paddle

Paddle with a dedicated guide as the Florida Gulf Coast sun sets