Need Advice on Itinerary

I can only choose to fly in and out via the same city. The choice is between Osaka or Tokyo. 2 persons are travelling on this trip.

If I were to choose Osaka, my itinerary will be as follows:-

22 April - Arrive Osaka 8am plus - Visit Aquarium

23 Arpil - Osaka to Kyoto - Gion

24 April - Kyoto - Arashiyama

25 April - Kyoto

26 April - Kyoto to Tokyo - Shibuya/Shinjuku/Ginza

27 April - Tokyo - Fish Market/Odaiba/Ueno

28 April - Tokyo to Odawara on Hakone Free Pass

29 April - Explore Hakone + shopping at Gotemba Premium Outlets

30 April - Tokyo

1 May - Tokyo

2 May - Osaka - Universal Studios

3 May - Osaka - Departure via 7pm flight.

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If I were to choose Tokyo as the entry/exit point, the itinerary will be as follows:-

22 April - Arrive 7am plus - Tokyo to Kyoto

23 April - Kyoto

24 April - Kyoto

25 April - Kyoto to Osaka - Aquarium

26 April - Osaka - Universal Studios

27 April - Osaka

28 April - Osaka to Hakone

29 April - Hakone + Gotemba shopping - Gotemba to Tokyo

30 April - Tokyo

1 May - Tokyo

2 May - Tokyo

3 May - Tokyo / Departure via 9pm flight

I will appreciate guidance on:-

a. Whether the itineraries makes sense in terms of allocation of time and travel.

b. Whether I need a JR Pass.

c. Recommendation of a ryokan, either in Kyoto or Hakone area.

Excited about this trip and looking forward to receiving feedback and comments on the above. Thank you in advance.

A 7 day JR Pass does not cover all your long distance train travel, a 14 day JR Pass is about Yen 8 000 more expensive than single tickets. Itinerary makes sense. For ryokan recommendation what price range?

Dear Peter

Thank you for your input.

I am most likely to use Osaka as the entry/exit point for my trip because I am having some difficulty in securing tickets to Tokyo for that period.

With that in mind, is a 14-day JR pass necessarily cheaper than buying tickets separately.

I know that travel between Osaka, Kyoto and Tokyo are on JR. I have also read that the JR connection is not that extensive for exploring Kyoto. Further, the side trip from Tokyo to Hakone can be on the "Romance Car" operated by Odakyu.

As for the choice of ryokan, I was thinking of experiencing it either in Kyoto or Hakone area. The budget is preferrably kept at no more than 30000 Yen a night.

One more enquiry - is it worth the while to shop at the Gotemba Premium Outlet when visiting Hakone?

Thank you in advance for your further input.