things to do in Osprey, FL

Reach offshore reefs for a varied seasonal catch

Cruise Siesta Key’s western coast with time for dolphins, a sandbar stop, and a swim

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

Reflect with sound bowl meditation in a styled picnic setting

Set your own course for snorkeling, island stops, sandbars, and dolphin searches

Ride a swimming horse through Palma Sola Bay’s waters

Paddle Midnight Pass on a private Siesta Key kayak or paddleboard tour

Cruise Sarasota’s Gulf Coast as the sun sets from a tiki boat

Ride an e-bike around Anna Maria Island with pedal-assist ease

Set your own pace on a self-guided coastal paddle

Rent a 23.5 ft Mako center console for cruising or fishing in Sarasota

Private waterway cruise with time to swim, float and explore a sandbar

Private reef fishing for seasonal offshore catches

Spend 4.5 hours cruising, snorkeling stops, and sandbar time off Siesta Key

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

A styled picnic with a charcuterie board and complimentary champagne

Design a private day of snorkeling, sandbars and island cruising

Ride from the beach into the water with one-on-one horse guidance

Learn to surf in Sarasota with a coach-led lesson

Sip mimosas while cruising Sarasota Bay and watching for dolphins

Paddle a tandem kayak from the canals to Tampa Bay

Paddle Gulf Coast waters and explore nearby islands at your own pace

Book a private clear-kayak tour with a guide for groups up to 14

A private eco cruise to spot dolphins, manatees, and shorebirds