Just space them out out or even take a couple days to visit Japan. Some airports even have programs where they'll take you on a field trip during your layover
These suggestions are cognitive load on the person making the trip. Most people break out in sweats thinking about organizing a trip to begin with, booking something with any complexity or risk is unbearable to them. My parents are both like this.
I had a partner like that. Would freak out if I started driving without our destination already in the GPS.
I think at least half of travel should be an adventure. Adventures are uncomfortable - but they make the best stories. Nobody has ever said, "Man, remember that time we went on that perfectly planned trip where nothing out of the ordinary happened? How exciting!"
Sure I remember the adventure in Denver that one time, but we barely made it to the funeral the trip was about, and we missed a lot of time with family.
If you just want to travel randomly, then no plan is fine. However we laid out plans can ensure you get to the must sees that are farther from home. Also many close to home things have wierd hours They are open so if you don't plan you won't see them that trip.
When you have a kid and a stressful job and adventures shooting out your ears in day to day life, sometimes the idea of going to Guam and swimming in the beautiful waters and relaxing is what you want out of travel. Adventures don’t have to be exotic, I live adventures daily, and I spend a lot of my life uncomfortable. Many people do. The idea of the adhoc adventure trip i think resonated a lot more with me when I was single or newly married. Now, I love a trip to Bora Bora - my wife is very organized and loves travel planning, and we have perfectly executed trips where the excitement is snorkeling with sharks and mantarays rather than spending 48 hours laying on the floor in a foreign airport with a 9 year old.
Heck, I enjoy a good adventure. But I want the adventure at my destination. There is nothing relaxing or exotic about missing connections and spending the night on a dirty concrete floor.
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?)
