Solo Spring Trip (Tokyo-Hakone-Osaka)

Hello! Now that restrictions have been lifted, I’ve decided to go to Japan from Late March – Mid April. I would love some advice on this itinerary:

3/29: Arrive in Tokyo

3/30: Sensoji + Getting unpacked/adjusted

3/31: Ghibli Museum + ??

4/1: Ikebukuro (sunshine city and ramen)

4/2: Yokohama (cup noodle museum and sankeien gardens)

4/3: Ueno park (or other good place for hanami, hopefully one that also has wisteria maybe?) + akihabara

4/4: Teamlab planets + Tsukiji fish market (the outer market, not the fish auctions but open to changing that! I just have a sensitive stomach)

4/5: Tokyo DisneySea (I thought it would be a fun, relaxing way to spend a day and take photos, but I’ve heard mixed reviews on whether it’s worth it)

4/6: Shinjuku (shopping) and Omoide Yokocho for food in the evening

4/7: Check out of Tokyo hotel, take train to Hakone, drop off luggage at the ryokan if it’s not check-in time yet, then possibly gora park or owakudani depending on how much time I have

4/8: Open air museum + Check out of ryokan then travel to Osaka and check in there

4/9: Osaka Castle + Getting adjusted (I’m very bad at using public transit/directions in general so I’m baking in this time so I don’t get lost)

4/10: USJ

4/11: Travel to Tottori (specifically to Conantown) for a daytrip

4/12: Travel to Nara (manyo gardens, nara park, and todaiji if I have time)

4/13: A free day for shopping/souvenirs

4/14: Check out + head back up to Tokyo (either by train or plane) to depart from HND

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A few things I’m wondering:

1) Is this too sparse or busy? Will I be able to get all this done? Will I be idle for long periods of time?

2) What are the best travel methods for these locations? I’m planning on getting a JR Pass, but should I get a 14-day one and supplement with the Suica card? Is there a better way to do it? I’m also really bad with directions so the simplest thing that works with google maps would be best for me.

3) Are there things I’m missing out on that would be great for me (especially with regard to events or matsuri?)

4) How should I prepare before going to japan (like should I get a sim card or pocket wifi there or reserve before I leave?) I know JR Pass has to be ahead of time, but is there anything else like that?

5) Do you recommend booking most restaurants ahead of time or waiting till I get there?

About me:

I am a tall (5’9″), plus size (1X US), brown girl, so I know I will stick out in Japan. I want to be able to have many of the same experiences though, so I don’t mind bringing my own yukata for the onsen experience, etc. Just need to be aware of whatever I need to do to prep!

Budget-wise I’m pretty flexible as I’ve already booked my hotels and flights and came in right on budget targets. For the rest of the trip I was hoping not to go over $8k for food, transit, tickets, souvenirs, etc., which I don’t think I will as it’s only 2ish weeks. Is this realistic? I can set aside more money if needed.

I speak a little Japanese (about N4 on JLPT scale) and I like anime, some video games (nintendo mostly), art, and gardens. Some of my favorite Japanese musicians are Eve, Kenshi Yonezu, Yoh Kamiyama, THE ORAL CIGARETTES, and Official Hige Dandism, but I haven’t been able to find concert information during that time. I’m also planning to get reservations for fancy restaurants like michelin star ones, but I’m not 100% sure the best way to go about that online.