Best 463 things to do in Osprey, FL

Soar above Siesta Key and spot dolphins on a safe, family-friendly 2.5-hour parasailing cruise

Spot playful dolphins and relax at a scenic sandbar while enjoying complimentary drinks

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

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

Cruise Siesta Key’s shoreline from a beachfront pickup point

Soar up to 1,200 feet and enjoy panoramic views on an exhilarating parasail ride.

Rent a 20' deck boat with Bluetooth stereo for up to 10 passengers

Rent a 21' deck boat for up to 10 and cruise the Intracoastal Waterway or Gulf

Cruise the Intracoastal Waterway on a 22' pontoon, up to 12 passengers

Rent a 26' Panga for fishing or diving, up to 6 passengers

Rent a single or double kayak for 4 or 8 hours

Rent a 20' deck boat for up to 10 passengers on the Intracoastal Waterway or Gulf

Rent a 22’ deckboat for up to 10 and cruise the Intracoastal Waterway or Gulf

Rent a 22’ pontoon for up to 12 on the Intracoastal Waterway

Rent a 22’ pontoon for up to 12 on the Intracoastal Waterway

Rent a 22’ pontoon for up to 12 on the Intracoastal Waterway

Chart your ideal day on Venice waterways with a licensed captain

Private 1 hr 45 min sunset cruise for up to 6 with a licensed captain

Explore Siesta Key with room for your belongings

Explore Siesta Key on a street-legal scooter built for two

Explore Siesta Key at your pace with flexible golf cart rental times

Choose a bike style and rental length for easy Siesta Key exploring

Get out on the water with free delivery on Siesta Key

Flexible golf cart rentals for exploring Siesta Key at your pace