First of all, I openly take responsibility for my dog being spoiled, but he is almost 5 years old and has never been crate trained. He stays in my bedroom each day when I go to work and he does fine alone, he usually just sleeps all day. However, my boyfriend and I would like to start taking him on vacation with us rather than board him because he gets so depressed when we do and refuses to eat the entire time we're gone. He doesn't like being left alone is unfamiliar territory though and I know he will freak if we leave him alone in a hotel room for a period of time. I'd like to train him to be comfortable with the crate but I'm not sure where to start since he's older and not used to it. Can anybody offer any suggestions?