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Help with Japan itinerary for second half of April

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My husband and I will be spending almost 2 weeks in Japan in the second half of April. For the first 4 nights, we will be staying with friends in Tokyo. I have a rough idea of what I think will work, but need help in fleshing it out, making sure distances are reasonable and getting any advice on hotels, restaurants, guides or anything that would help us. Having never been to Asia, I'm a little overwhelmed with planning this trip.

Please tell me what you think.
Nights 1-4 Tokyo
Nights 5 and maybe 6 Hakone
Nights 6/7 - 10 Kyoto with day trips to Nara and ??
Night 11 and maybe 12 Staying at Monjuso Inn in Amanohashidate (friends stayed there and highly recommended)
Night 12/13 Back to Tokyo to finish anything we missed
Day 14 Afternoon flight out of Narita

We are good travelers and enjoy walking, hiking, and biking. We'd like to see a combination of cultural sites as well as natural beauty.

Do you think it's better to stay in one place in Kyoto and take side trips or to stay in several places? Is it important to see Osaka, and if so can it be done in a day trip or is it better to stay overnight?

I realize that my questions are all over the place, but with a little help, I can refine this and get to more specific questions.

Thanks for any and all help!!!

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