14 day trip to Japan

Hi, I am planning my first 14 days trip to Japan in end November, would like to know if my below itinerary look ok if all by trains:

1. Arrive Osaka - 2 nights
2. Kyoto - 3 nights
3. Takayama - 1 night
4. Mt Fuji - 1 night
5. Hokkaido - 2 nights
6. Tokyo - 4 nights

Our concern is if the above itinerary are too pack and if there is any train from Mt Fuji to Hokaido.

Looking forward your advice.

Thanks,
Kelly

Your journey is not that packed. It depend are you good at public transport and not get disorientated. Luggages? Between Kyoto-Takayama, Takayam-Fuji, Fuji-Hokkaido, I think there will be several changes on train (keep that in your mind).

You need to check on Hyperdia for exact time and duration. I guess
Kyoto-Takayama 3H?
Takayama-Fuji 5H?
Fuji-Hokkaido 8-12H?

For Hokkaido, where you going? Hakodate is closer by 4H then Sapporo.

I recommend your hotel to be close to station was swifter journey.

As for Fuji to Hokkaido, You need to get to shinkansen station or Tokyo Station to connect a train to Shin-Aomori.

I been Shin Aomori last year, just get off the train follow the crowds or sign to catch the train to Hakodate. Most shinkansen (at least the fast one) arrive to catch a train to Hakodate, so don't stop and take photos.

Kyoto - Takayama = about 200min
Takayama - Fuji (where exactly? Fujinomiya, Hakone, Fuji Five lakes?) = If I assume you will stop at Fujisan station, about 400++ minutes
Mount Fuji - Hokkaido (where? Hokkaido is huge) = I assume Hakodate as first stop, about 700-900 minutes depending on connection , Hakodate to Sapporo another 200minutes but be aware of the last train departing to Sapporo if you plan to Mount Fuji - Sapporo
Hokkaido (where?) - Tokyo = Assuming Sapporo, about 800 minutes.

With not much details on your daily itinerary,your main concern is the amount of time on train when traveling between places, unless you have planned to use planes for some area (Hokkaido).

To go from Mt. Fuji to Hokaido you'll need at least one train change at Tokyo, or one at Tokyo and another at Aomori.
Anyway, having that in mind, I would skip Hokaido entirely with that kind of itinerary. Don't think is worth the trip.

Take overnight trains to stay time
Leave luggage at train station lockers
Travel hard core
Shower at hotel
Sleep hotel
Travel hard core
Return train station
Take luggage
Overnight train again
Overnight train, Hokkaido; Osaka; tokyo

I would also recommend dropping Hokkaido. It won't be worth the effort for such a short stay, and will free up more quality time to spend in Takayama or around Mount Fuji.