In the region I live, I've heard some people saying, "How is it to play golf wearing sneakers?" Although I believe that it should be 'What is it like to play golf wearing sneakers?' Am I right in this?
"What is it like" is usually followed by an infinitive (to play) or a present participle (playing). Grammatically and idiomatically, it almost always works.
"How is it" is usually followed by a present participle. Grammatically, it doesn't work as often as "what is it like", but people still use it even if it isn't grammatically correct.
In casual conversation, it's not a problem to break grammar rules. In more formal contexts, where you have to speak English perfectly, you would probably use "what is it like".