My sister and two friends and I took the Lower East Side Tenements, Tales and Tastes walking tour in October and once again, had a ton of fun. Brian Hoffman was our guide for the speakeasy tour we'd taken prior and I highly recommend requesting him if possible. He is a food blogger always has great food and drink rec's.
Our tour started near City Hall, went through Chinatown, Little Italy, and the Lower East side. Along the way we sampled foods from the various immigrant cultures that have passed through those areas and learned a wealth of knowledge about the history of this part of Manhattan. A surprise stop was the African Burial Ground National Monument, which I had never heard of prior to the tour. It was a powerful experience. I highly recommend Urban Adventures as your "go to" choice for a unique, fun, interesting way to learn about NYC.