things to do in Osprey, FL

Private 2-hour cruise to look for dolphins, manatees, and more

Unwind on a private boat as the sky shifts into sunset colors

Dock-hop waterfront bars with a licensed captain at the helm

Get kayaks or paddleboards delivered straight to your Siesta Key resort

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

Choose a bike style that fits your plans for a full day on Siesta Key

Ride Siesta Key and reach the Legacy Trail with an e-bike rental

Ride paved trail miles from Sarasota toward Venice

Learn the ropes with hands-on help from hook baiting to fish cleaning

Savor Sarasota’s flavors and history in one unforgettable afternoon!

Taste your way through Downtown Sarasota with a guided history walk

Eat your way through historic downtown Sarasota with four restaurant stops

Stroll St. Armands Circle and enjoy a guided lunch tasting

Taste your way around St. Armands Circle on a 3-hour afternoon tour

Sip signature cocktails and learn the stories behind Sarasota’s spirits

Trace Anna Maria Island's haunted history along Bridge Street

Trace the women who shaped Anna Maria Island

Taste island food while uncovering Anna Maria Island's history

Taste creative tacos, sip margaritas, and discover Sarasota stories

Explore Sarasota's paranormal tales and historic murders after dark

Private inshore fishing charter with short runs and all gear included

Target Florida game fish with bait, gear, and fishing licenses included

Explore Anna Maria Island and Tampa Bay with stops tailored to your group

Target tarpon with Captain Rachel’s 10+ years of local experience