My Question to You

I need help. (That's not unusual!) But what I need help with is advice on a travel bag. I am going on an international trip (ie Caribbean) and I want to have a bag to take on the plane (carry on) that will also be great for shopping and sight seeing trips. I like it to be organized so I can quickly locate pens, paper, travel itinerary, and my inhaler (in case I need it quickly). In the past I have always used a backpack, but I am looking for something a little different. Oh and of course it should look terrific and stylish! What should I check into getting for toting things? Share your ideas!