As they lead groups through the heart of Times Square, Manhattan Walking Tours' licensed guides tailor their narration to the interests of each of their up to eight participants. They follow an organic, ever-changing tour route as they answer questions one-on-one and strike up conversation with each urban adventurer, eschewing common tour-guide tactics such as screaming the names of U.S. presidents. As they navigate city history from 42nd Street to 47th Street, the guides use their experience as actors and city museum historians to entertain and educate their small groups. They're also undeterred by parades and seasonal events, taking alternate routes when necessary to cast a light on the history of often-unseen landmarks. At times, they venture right into the special-event happenings to grant visitors a glimpse into city culture.

Over the course of each tour, guides expound on some of the city's oldest architecture, pointing out buildings in the Paramount and Beaux-Arts styles among other stone and glass structures dating back to the late 1800s. Underneath vibrant billboards and twinkling theater marquees, they reveal secrets of the famed theater industry, such as why Sardi's Restaurant became the place for theater artists to wait for their reviews. They also let guests in on ancient questions such as why the city decided to drop a ball on New Year's Eve, how Times Square got its name, and which pizza chef the Tony Awards were named after.