It's not impossible to do. It just sounds silly that the best way to take a 5 day trip in Guam is to take a 2 day trip in Japan and a 3 day trip in Guam.
I wonder if there's a big list of places that take unintuitively long to get to? Friend of mine flew from California to South America a few years ago by way of Paris (which I think is a requirement for French Guiana?)