civil

Ideally in Florida, but that may not be possible. I'm not sure why you want to sue him, but, generally, if it's for something that occurred in Florida, you should be able to sue him in Florida, in the judicial venue where a substantial part of the events leading to the lawsuit occurred. Otherwise, you may have to sue him in New York, in the judicial venue where he resides.

But that begs the question, is it worth it to you to file a small claim in New York? A couple flights alone will cost you more than you'd recover. Think about the costs you'll incur filing your claim. Don't throw good money after bad.

I agree with the prior answer. Consider whether you have a right to recover attorney's fees or other costs.

Also, if you are able to proceed in Florida, you may have to domesticate your judgment in NY, unless the Defendant has assets in FL. You would probably want to hire a NY attorrney, but at least at that point it is just collection and depending on how much your judgment is for and how hard it is likely to be to collect, you have to decide if it makes sense economically to pursue it, and if not, whether it is worth pursuing for other reasons. (It's usually not.)