Anyone spend 3+ weeks in Japan without an itinerary?

I'm not good at planning trips and for the most part my preferred activity when traveling is just wandering around. I would like to spend around 3 weeks seeing various parts of Japan that I didn't get to on my first trip almost 10 years ago. My plan is to land in Tokyo and then use a JR rail pass to visit places like Nagano, Osaka, etc each for a few days, and ideally more off the beaten path spots on the way. From posts it seems like people don't generally recommend the rail pass but as someone who loves riding the trains in Japan and is hoping to take a lot of shorter trips it seems like not a bad idea. Just wondering if anyone here has done something similar.

by rosehipnovember

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