Best 468 things to do in Osprey, FL

Tailored private cruises for sunsets, wildlife, and celebrations

Fish Anna Maria waters with a fourth-generation local captain

Explore quietly with long-range lithium electric power

Cruise Anna Maria Island with a street-legal gas golf cart

Street-legal gas cart with modern onboard features for island travel

Ride a street-legal double-seat scooter around Anna Maria Island

Explore Anna Maria Island in a street-legal ScootCoupe with trunk storage

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

Take the controls of a locomotive for an hour

Ride an enclosed coach to a pumpkin patch with games, hay rides, and pumpkin picking

Ride an open-air train to the pumpkin patch for games, hay rides, and pumpkin picking

Assigned First-Class Seats for a Pumpkin Patch Rail Trip

Reserve a private caboose for your group’s pumpkin patch train outing

Watch a Civil War battle unfold from aboard a heritage train

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

Bring music and evening lighting to your group ride

Paddle Anna Maria canals or venture into Tampa Bay

Roll across sandy beaches with balloon tires

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