What motorcycle is right for me?

I am five foot eight, eighteen years old. I weigh 160 pounds. I want to be able to ride up to 5 hours to visit friends at colleges far from mine. I have to pay for my own insurance, so minimizing costs on that would be great. I want to be able to safely/ comfortably go on the highway for long distances. Also important is it looking good. I like the Honda Rebel 250, but worry it wouldn't be able to handle the trips... and advice would be really helpful. Thanks a ton.