10-day Feb. Itinerary - 1st Timer Need Input

Fiance (soon to be wife) and I are planning our trip to Japan from February 18th (19th arrival)- March 2nd (departure).

We've traveled to a few different places, but the train and bus situation as well as the sheer variety of destinations is quite different than what I am used to planning.

I'm juggling the below itinerary ... does it seem feasible / enjoyable? We're trying to find a good mix of old and new with enough time to wander around primarily in Tokyo and Kyoto.

19th - arrival 4:30 pm, check in to hotel, get dinner, go to sleep

20th - full day tokyo (various sites in/around Shinjuku)

21st - day trip to Nikko (full day), evening out in Tokyo / or sleep depending

22nd - full day Tokyo (likely in the Taito area)

23rd - depart for Kyoto early morning, check into hotel, wander / get dinner

24th - full day Kyoto

25th - day trip to Nara

26th - full day Kyoto or day trip to Osaka

27th - depart to Hakone, check in to Ryokan, evening meal / relaxing

28th - depart to Tokyo mid afternoon / dinner in Tokyo

1st - full day Tokyo? Day trip? Not sure

2nd - final breakfast / lunch / shopping - departure to airport at 3 PM

We will be getting the JR pass & the Nikko bus pass ... Not sure if we should get the 14-day on arrival or the 7 day when we leave Tokyo for Kyoto... We were planning to use the JR lines to visit Nikko without added cost, and would use it for the trip to Nara. Hakone I believe requires a couple of different trains for the side-trip.

Any major flaws / problems here anyone can see? Will any of this be a disaster or suck in February weather? Should we stay an extra day in Kyoto and push the trip to Hakone forward a day (eliminating the return full-day in Tokyo)?

Any input is greatly appreciated, I feel totally out of my league here !

Ah sorry, forgot to add we are flying into and out of Tokyo (HND)

I think you're trying to pack too much into what really isn't very many days. Kyoto should have at least 2 or 3 full days for a first time visit, and Tokyo around 4 or 5 (and you still won't be able to see/do everything!). Consider staying in just one area only (Tokyo and surrounds, or Kansai) and see it properly, or rearrange your flights to arrive in Tokyo and depart from Kansai (or vice-versa).

If you do stick with your current itinerary, a 14-day JR Pass is highly unlikely to pay off. Get a 7-day JR Pass to cover the round-trip between Tokyo and Kyoto, as well as the trip to Nara. Perhaps consider rearranging your itinerary so your Nikko day is the day before you leave for Kyoto, and then the JR Pass can cover Nikko, Kyoto, Nara and Hakone, getting you more value.

The JR Pass will get you most of the way to Hakone on the shinkansen; you'll just need separate tickets from Owakudani.

Ah that makes a lot of sense!

I can rearrange to visit Nikko on the 22nd, then I can make it back to Tokyo for the 1st on the 7 day pass.

You think it's too much stuff for the time frame? I was worried about not having enough to do.

We're looking to stop off at a ryokan with a private onsen and Hakone seems to stand out. Is it a good place en route to fit this in?

That looks pretty good to me as long as you are travelling light. Remember in Japan it is freezing outside that time of year but like the surface of the sun inside and in public transport, so dont layer or else you will melt. Just invest in a good longish heavy jacket.

On the 28th (from Hakone) I'd go to Kamakura and spend the night there and most of the next day. Kamakura/Enoshima is full of stuff to do and during winter it is relatively quiet. We usually stay at Iwamotoro Honkan at Enoshima which has views of Fuji in the mornings.

I am a slow traveler and for the time you have at hand and being a first trip to Japan I would not say that your itinerary looks too busy.
I personally would skip Osaka and use the day for Kyoto but not changing accommodation means that you can decide each day, so that is good.

A 14 day pass won�ft pay off.

For Nikko if you want there is also a standalone pass with a private railway company. Nikko as a daytrip would be challenging for me ( not a morning person). But it is a nice destination. It can be quite cold though. Alternatively you could go to Kamakura/Enoshima that day. Or do it on your return from Hakone and spend the last night before your flight in Kamakura. (Personal favorite:Kitakamakura).

For your Ryokan experience remember that you need to checkin around 17:00 so that you are in time for dinner and bathing. This unfortunately means that you only have the early morning in Kyoto that day.

Enjoy your trip to Japan!

Unless you're going to USJ, a lot of the day time sights in Osaka are not that compelling. If it were me, I would combine by Nara/Osaka days and just get back to Kyoto late. A lot of Nara sights are going to be closed come 17:00 and Nara will start to get dark. You can take JR from JR Nara Station to Tennoji and then go to where ever you want in Osaka or just even pay out of pocket and use Kintetsu. Most people want to see Dotonbori and Namba. You can shop or eat and then head back to Kyoto.