Shibuya station to Nakatsugawa station

I am going to Japan on December 2nd and will be staying two nights near Shibuya station. My trip is to go to Nakatsugawa station on December 5th and I will probably leave around 10AM so I can get there before the evening. Also I don't know much Japanese. I'm just seeing if anyone has personal experience about travelling that far alone in Japan? It is about a 5 hour trip with trains and such.

Thanks.

Essentially, you need to get a Shinkansen from Shinagawa to Nagoya, then a train from Nagoya to Nakatsugawa.
From Hyperdia, if you are prepared to leave a little earlier, the easiest would be
SHINAGAWA 09:17
SHINKANSEN NOZOMI 19
[94 Min]
10:51 transfer NAGOYA
11:00
Arrival track No.16 / Departure track No.10
\7,020
[49 Min]
LTD. EXP (WIDE VIEW) SHINANO 9
11:49 NAKATSUGAWA

So you would need to leave Shibuya in the Yamanote line around 8.45am, and have everything booked in advance.
Good luck!

http://www.hyperdia.com/en/
if by Shinkansen via Shinagawa and Kanayama
if No Shinkansen(click SearchDetails) via Yokohama and Kanayama
Also Tokyo(not Shibuya) to Nagoya by Exp(high)way bus cheap
if no by Japan Rail Pass or Puratto Kodama plan.

BTW,why Nakatsugawa that date? something special?
If no and after 10 Dec possible by Seishun 18(juhachi) kippu cheapest 2370Y.
But 18 kippu price is not 2370Y. Open bellow link.
http://www.jreast.co.jp/e/pass/seishun18.html
And where to go after Nakatsugawa? stay Nakatsugawa? No back to Tokyo?

I will be going to there for my host family for a month then I will be going to Wakayama Prefecture for the last two months :)