I would vote for flying. I have a highly anxious pup. I travel with him often, and he seemed to accept flying much better than a long car ride. Flights are more direct and are over with quicker. I took a red eye after exhausting him with his favorite activities all day. Everyone slept, including him. VS the car rides, he gets anxious after a few hours and there isn't much chance for him to stretch his legs. On top of that, there are not many hotels that are pet friendly. We've slept in the car with him before in a pinch, or, and I know some people would disagree with what I did, but I snuck him in to places. It pays that he's so quiet.
