“Free” is rarely a word spoken without some sort of strings attached. But in the case of the Kindness Cab, it means exactly that and more.

On Oct. 24, to promote his book of the same name and his National Geographic TV show, “Amazing Adventures of a Nobody,” Leon Logothetis began a journey that will take him up, down and all around the U.S. He will be stopping in 11 cities total, arriving in Chicago on Oct. 31, to give free rides to its people and give back to the local schools.

“One way that I came up with to give back is to get myself in an English taxi and to give free rides to people across the country, retracing my route from Times Square to the Hollywood sign,” Logothetis said. “Then I thought that I could have the meter running and, at the end of the trip, donate books to local schools in the cities that I pass through.”

He said he will be keeping track of the fare generated through the trips, even though he isn’t charging the passengers, and will use the proceeds he’s earned from his book to give back to each state’s schools through books and supplies provided by the nonprofit organization ClassWish.org.

Robert Tolmach, co-founder of ClassWish, said the recently founded charity allows teachers to make a wishlist of school supplies, and with the help of the community, provide the students with educational tools they need.

The partnership came about when Penny Sansevieri, who worked on the marketing of Logothetis’ book, told him about ClassWish.org, a project she was assisting pro bono. Logothetis said he thought the charity organization would be the perfect fit for what he was doing.

“We are thrilled to have been chosen, and all of those kids will be thrilled,” Tolmach said. “The shortage of classroom supplies and books in [kindergarten through 12th grade] schools is simply staggering. Books, computers, art supplies, sport gear, musical instruments and science supplies—it’s all gone, and the average teacher is now spending $1,200 [per] year of her own money for supplies for her classroom, which is both unfair and inadequate.”

Logothetis, a native of England and former brokerage firm employee, said he knew for a while he wanted to retrace the steps he took in his first journey in 2006. During that time, Logothetis sought inspiration and escape from his humdrum life and traveled across the country, relying on $5 per day to cover food, travel and accommodations.

But it wasn’t until being inspired by the travels of Che Guevara that he realized he also wanted to give back to the communities. So he purchased a 1985 London Sterling and began planning a trip that would give back to the country that gave so much kindness to him. He said his first day on the job in New York was very encouraging, and the positive reactions of the people, after hearing what he was doing, was the most rewarding aspect.

But how does one get a free ride from the Kindness Cab? People are able to request rides from Logothetis through Twitter, Facebook and a telephone hotline set up for the Kindness Cab’s trip.

Because the more cab rides he gives in each city means the more money generated for schools, he has been picking up as many people as he can, whether they RSVP’d or not. He said he was glad to see that although the passengers seemed shocked, their reaction to what he was doing—and the free cab ride—was positive. Followers of his trip are also able to track the amount of money he earns at KindnessCab.com.

The journey will also allow Logothetis to reconnect with some of the people who helped him in his initial trip, by staying at the houses of some of the people he met along the way.

“When I traveled across America, I was inspired to change my life because of the kindness I received and the opening of people’s hearts toward me,” Logothetis said. “I want to try to inspire someone else. I find that by doing something out of the ordinary, like the Kindness Cab, people [might] step out of their everyday lives and realize anything is possible, and if we can be civil and kind to ourselves and each other, slowly the world can change.”

Follow the Kindness Cab’s progress, including video content and a fare tracker, at KindnessCab.com. For more information on ClassWish visit the charity’s website at ClassWish.org.