unless you absolutely have the EXACT vision for what your trailer is going to be – and you are 100% confident you can get the interview subjects to say what you've envisioned – i have to tell you that it's going to take a lot longer than 2 days to cut a trailer. (i once thought the same thing, but 2 days goes so fast...)
theoretically, it really doesn't seem like it should take that long, but it always does. sure, you could cut a quick 2-minute trailer in two days but i guarantee you won't be happy with it. 5 days sounds like a much better estimation. if you are entering this contest because you actually want to win it, it's probably better to bring all the footage home and find an editor in NY or NJ.
Start looking now for the editor so that you can begin editing as soon as you return from Italy. Honestly, you probably aren't going to attract a top-flight experienced editor with your budget and project. but you can actually attract a decent (though inexperienced) editor for $200/day. 4-5 days editing with him/her will be roughly equivalent to what you would have spend with your Italian DP. If your editor is technically proficient, and you are very clear about what you want, you'll have a good chance at success.