3 Days in Osaka or Kamakura/Hakone in Nov

So my wife and I are spending most of our first trip to Japan in Tokyo. However, we still want to be able to see and experience some of the other parts of Japan so we booked 2 nights in Hakone and 1 in Kamakura. I am now wondering if I should've instead tried to do Osaka or possibly some other small town, mountain town, etc. that I hadn't heard of.

Is there anything that's an absolute must do over going to Hakone and Kamakura? Or is Kamakura not worth a night and I should either do another night in Tokyo or elsewhere? Sorry for the indecisiveness, I just can't get a firm opinion because there are so many options!!!

Firstly, your travel is next month so how will you just cancel/modify your bookings and expect to find alternatives in such a short time?

Secondly, how many days is your trip?

Thirdly, you can do Hakone and Kamakura as daytrips from Tokyo, and go to Kyoto or Osaka for 3 days.
If you decide to go to Osaka or Kyoto then on the daytrip to Hakone instead of returning to Tokyo, take the bullet train from Odawara to Osaka or Kyoto (whichever you find accommodation that suits your budget in).

In the end, if you don't get to Osaka or Kyoto this time, there is always another time to visit Japan and explore the Kansai region.

Personally with only three days, I'd stay in Tokyo, which is a great city and can easily keep you busy for this amount of time. If you feel bored you can easily (and for little money) get out of the city for a day visiting for instance Kamakura, Nikko, Hakone,.... This will save you plenty of yen compared to heading all the way to Kyoto/Osaka and back and in addition you won't lose time on transport, locating hotels, etc.

Osaka is nice, but it is too similar to Tokyo for first time visitors. Possibly keeping your current arrangements or booking some accommodation in Kyoto might be a good idea if money is not a problem. November can be expensive for accom in Kyoto due to fall colors. However, if your time is right it is one of the best experiences in Japan that are possible. Do note that crowds will be large in Kyoto on weekends in late November at this time.

How long is your whole trip? I am asking because if the whole trip is not very short, I might suggest traveling to and staying over in Kyoto for two or three nights instead (provided decent accommodation can be found).

If the whole trip is relatively short that that is a bit rushy to do the above, then two nights i Hakone, one night in Nikko might be good. (Kamakura is rather a commuting distance from Tokyo, IMHO, can be done as a day trip from Tokyo, and not really worth staying over.)

Thanks for the feedback everyone. Here are additional details:

Trip length 8 days with the first 3 and last 2 already booked to stay in Tokyo. So the middle three were where we were going to do Kamakura then Hakone.

So is it worth looking into Osaka or Kyoto? Or keep with Hakone and/or Kamakura (can always do something different if Kamakura isn't worth a day).

Thank you!!

Hi!

I guess the next real question is your budgeting. Going to Kyoto/Osaka is going to add on ~13,000 yen per person each way, not including sightseeing, accommodations, and food. (And yes I know you can take a slower Kodama for ~10,000 yen but why would you want to spend close to 4 hours sitting on a train to save 3000 yen, and if you really need to save 3000 yen that much going to Kyoto for 3 days might not make financial stress as is.) You can get a 7 day rail pass, but it would behoove you to make sure you get your money's worth of the ~29,100 price.

The plus of Kamakura, Hakone, Fuji Five Lakes and Nikko is they're all less built up from Tokyo and are quite pleasant and can be reached with cheaper passes/tickets like Tokyo Wide, or Odakyu Hakone.