>>2837695
>>2837784
Koyasudori in Yokohama. It's one of the few oldschool ungentrified wharfs left. I'll go there in a couple weeks and post photos in this thread. If that's not enough, then Yamashita Pier in Yokohama or the ports near the International Cruise Ship Terminal in Tokyo I guess.
>>2837769
I'm also from Boston. Fly to LA first and take a ZIPAIR flight to Tokyo from there. The JR pass isn't worth it in 2025. Take a night bus from Tokyo to Osaka and then take a local train to Kyoto if money is a concern. I wouldn't really recommend hostels, capsule hotels, or Okinawa (for your first trip). Try to focus on a general golden route itinerary first and then combine Okinawa with Kyushu, Taiwan, or Guangdong/Hong Kong for a separate trip.