Second Guessing my itinerary

I have a flight booked and cancellable hotel reservations for 8 nights in Tokyo right outside a subway station near Asakusa. Plane lands afternoon of April 4 and departs in the evening on April 12. That gives 7.5 days in Japan. My plans are to spend 3.5 days seeing different districts of Tokyo, and take day trips to Hakone, Matsumoto, Kamakura. I have one day open that I can either relax in Tokyo, or be spontaneous and pick another day trip based on how things are going. Does this sound like a reasonable plan?

My problem is that now 2 months after planning this, is that I can't get out of my head that I should stay some of the trip out of Tokyo. Am I making a mistake sticking to just the Tokyo area? I probably won't get back to Japan any time soon.

Day trip to Matsumoto sounds like a bad idea.

I agree, Matsumoto is a bad idea. You'll waste too much time on public transport. Unfortunately 8 days is not a lot so it's inevitable for you to miss things. I've probably spent about 7-8 weeks in Tokyo alone over several trips and there's still places I haven't explored. Choose what interests you most and limit yourself to those 2 daytrips.

Depends on what you want to see, but if you want to see a bit more of Japan, I might drop one (or two) of the nights in Tokyo, and make an overnight (or 2-night) trip to Kyoto.

Kamakura is an easy day trip from Tokyo, Hakone can be done but you'd want to start early from Tokyo, and do not go on the weekend (more crowded).

You might want to look under Plan a Trip - Itinerary Suggestions (of this website).

I think given the shortness of your trip staying in Tokyo & day tripping is the best option. At most I might change hotels from one side of Tokyo to the other at some point for a change of scenery. I agree with others re: Matsumoto, I enjoyed Yokohama & Nikko is always worth a visit.

Thanks for the feedback.

I know Matsumoto is kind of far, but I just really wanted to see a nice original castle. If I catch a good transfer at Nagano and use the bullet train with a JR East Nagano pass, it looked like I could do it in 2.5 hrs each way from Ueno for a reasonable price.

I was also planning on leaving early and spending maybe an hour at Odawara on the way to Hakone. So I would see at least one castle either way.

if you still go to Matsumoto for the castle, I really recommend to take a volunteer English-speaking guide for tour. We had and got really nice excursion with retired post-office boss.
Btw - you need to take shoes off in this castle.
Allow then also some hours for Matsumoto other sights - Nakamachi, or even ukio-e museum.

Crazy idea. Turn the day trip to Matsumoto into an overnight. Stay the second half of your trip in another part of Tokyo.

If you are OK with long train rides (about 2.5 hr each way, as you noted), a day trip to Matsumoto is doable. I have done even longer day trips, and I enjoy riding trains. If you have never visited a Japanese castle before, you may want to visit Odawara Castle on your trip to Hakone first before going all the way to Matsumoto. I visited several castles, and I found out that I am not that much into castles. So, castles are no longer in my itineraries. It's one of those things you don't know if you enjoy until you try it.