Best 463 things to do in Osprey, FL

Cruise Siesta Key with easy pedal-assist power

Ride side by side on two jet skis in Sarasota Bay

Ride Sarasota Bay together on three jet skis

Bring your crew together on four jet skis in Sarasota Bay

Take the controls on a high-performance jet ski built for one rider

Private Gulf Coast cruising tailored to your sandbar, beach, and snorkeling plans

Customize a Sarasota cruise with an experienced captain

Cruise Sarasota’s waterways between waterfront restaurants and tiki bars

Relax on Sarasota Bay as sunset colors fill the water

Private fishing trips with gear, bait, licenses and catch filleting included

Explore Florida waters on a private charter with space for your snacks and drinks

Slide, snorkel, and swim on a private double-decker charter

Private evening cruise on Florida waters with room for your snacks and drinks

Cruise by boat to Rumbay Restaurant on Private Palm Island

Search nearby beaches for shark teeth and seashells from a shaded tritoon boat

Cruise to a sandbar with a jet ski, paddleboard, and snorkel gear

Cruise Siesta Key by e-bike with a rental timed for sunset

Cruise open water for sightseeing, swimming, parties, and sunset views

Learn shoreline fishing techniques with a captain along Sarasota's Gulf Coast

Target snook from Sarasota's shoreline with a guide

Stretch, unwind, and rejuvenate—right in the comfort of your vacation rental.

Paddle Jim Neville Marine Preserve to water-only Midnight Pass Beach

Launch from Turtle Beach and paddle to Midnight Pass

Paddle the mangrove tunnels of Ted Sperling Park with a local guide