Best 463 things to do in Osprey, FL

Paddle Midnight Pass on your own schedule

Explore Midnight Pass at Your Own Pace

Explore Midnight Pass on a self-guided, all-ages paddle

Ride a Jet Ski through Phillippi Creek and toward Siesta Key

Sunset jet ski ride with fast Gulf access from Siesta Key

Ride professionally maintained jet skis with Gulf access in Sarasota

Ride farther with a 30-mile-range hybrid and dual suspension

Ride a rustproof, belt-drive cruiser built for salt, sand, and coastal conditions

Ride Sarasota at your own pace on a 50cc scooter built for two

Get kayaks or paddleboards delivered straight to your Siesta Key resort

Cruise Siesta Key with a Class 1 or Class 2 electric bike

Explore Sarasota at your own pace on a fully equipped Aventon Pace 500.3 e-bike

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

Cruise Siesta Key’s waterways on a 2024 tiki boat with music, drinks and coastal wildlife views.

Soar over Siesta Key’s coastline with an optional Gulf dip

Enjoy a relaxed evening cruise along Siesta Key with music, LED lights and possible dolphin sightings.

Rent a 26-foot tritoon with seating and shade for up to 12

Rent a 26' tritoon for a full day with seating for up to 12

Cruise Sarasota Bay with a 17-foot deck boat rental

Rent a 25-foot pontoon for up to 12 people for a full day on the water

Rent a 23-foot pontoon for up to 10 people

Cruise and anchor around Sarasota Bay by deck boat

Rent a 21' deck boat for up to 8 people on Siesta Key

Rent a 23-foot pontoon for up to 10 people