Best 191 things to do in Osprey, FL

Paddle Lido Key mangrove tunnels with a private guide

Paddle Lido Key’s mangrove tunnels from Ted Sperling Park

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

Learn to surf in Sarasota with a coach-led lesson

Paddle Sarasota’s mangrove tunnels on a 2-hour guided kayak tour

Kayak Little Sarasota Bay to South Lido’s shaded mangrove tunnels

Kayak Sarasota’s mangrove islands with an experienced guide on a 2-hour afternoon tour

Paddle the Lido Key Mangrove Tunnels with a 4-hour single or tandem kayak rental

Rent a single or tandem kayak and paddle the Lido Key mangrove tunnels

Pedal kayak Sarasota Bay to seagrass beds and mangrove tunnels

Pedal kayak 2 miles through mangrove tunnels at Emerson Point

Pedal through seagrass beds and mangrove tunnels on a 2-mile Neal Preserve tour

Fish 11–14 miles offshore with gear, bait, and license included

Explore Sarasota's historic neighborhoods and cultural landmarks on a 90-minute air-conditioned trolley ride.

See Sarasota’s Art Deco, Mediterranean Revival, and Mid-Century Modern architecture by van

Join an interactive circus-themed whodunnit on a rolling Sarasota trolley

Ride a Sarasota metaphysical trolley tour with sound healing and mini tarot readings

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

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

Cruise at sunset with a sandbar stop and a closing toast