whatever you do, I would not check the lap top. It will likely be damaged. Are you trying to carry on a tote and a rollerboard? That may not work overseas. I have a Briggs and Riley "at work for her" case that slides over the handle of my rollerboard. I keep my laptop in it and have had no troubles in Europe.
I have had trouble with fruit before. It is supposed to be a big no, no bringing it in to the states. I saw some one get busted by the USDA dog once over a banana!
I recommend Briggs and Riley but it still needs to be 1 carry on and 1 personal item.