Best 192 things to do in Osprey, FL

Set up a 3-hour sunset beach picnic for two

Ride a 13-mile historic railroad excursion in open-air or air-conditioned cars.

Visit the gift shop and model railroad display in Parrish

Take the controls of a locomotive for an hour

Rent a street-legal 6-passenger golf cart with delivery included

Paddle a tandem kayak from the canals to Tampa Bay

Rent cornhole for easy, all-ages beach-day fun

Play Slammo at the beach with a 1–7 day rental

Rent a street-legal 8-passenger golf cart with delivery included

Rent a beach cruiser with delivery, helmet, and lock included

Customize a 4-hour private cruise with snorkeling, paddleboarding, dolphin watching, and more.

Rent a kayak or paddleboard and explore Turtle Beach waterways with a provided map

Rent a pedal kayak and explore Sarasota Bay with all gear and safety equipment included.

Tour Sarasota’s Pinecraft community to learn Amish and Mennonite culture

Ride an air-conditioned trolley at night for musical ghost stories and Sarasota history in October.

Rent a kayak or paddleboard for 4 hours with gear, route map, and lesson

Paddle into a Florida Gulf Coast sunset with a guided kayak tour

Paddle a private sunset route with a dedicated guide in Sarasota Bay

Paddle Lido Key’s mangrove tunnels with a private guide from Ted Sperling Nature Park

Ride the latest 3-seater jet skis and enjoy hassle-free fun on the water.

Cruise with up to 13 friends on a spacious pontoon equipped for sandbar hopping

Customize a private 3–6 hour cruise to Egmont or Passage Key with snorkeling and sightseeing led by experienced captains

Practice yoga on a paddleboard and connect with nature in a tranquil setting.

Explore mangrove tunnels by kayak or paddleboard with experienced guides in Neal Preserve.