commute between Amsterdam - the Hague is like 40min so don't let that hold you back...
I lived in both Amsterdam and Rotterdam and although both cities def have their pros and cons, and Rotterdam is the better skate city (bombed in ww2), I'd suggest that for a short trip like yours, and witouth a guide/local connect, you still visit Amsterdam instead. I can point you in the right direction, avoiding the tourist traps.
if you still decide to go to Rotterdam I can provide tips aswell.
And for Ghent, my sister and some friends studied there, it is the perfect (sized) city for a short trip.
pm me anytime
[edit: as for your board, Thanksgiving is November right? chances are it will be raining anyway, so if you weren't planning to skate, or use it to commute, then maybe don't. If you did (, to commute) set up some big(ger)/soft(er) wheels.]