There are 2 adults and we will be in Japan for 2 weeks.
Arrival in Japan May 26th
Tokyo May 27th
Tokyo May 28th
Tokyo May 29th
We then plan to take the train towards Osaka and visit various locations along the way.
Shizuoka May 30th
Nagoya May 31th
Osaka June 1st
Kyoto June 2nd.
June 3rd Return to Tokyo.
We are kind of just winging it and don't have anything that is FOR SURE.
I am worried about purchasing a ticket that doesn't pay off for the trip but at the same time I don't want to be stuck where I wish I had the pass extended.
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Comments
If you can get all your travel within seven days, I would purchase the 7 day pass. For example if you active your pass on your first train journey to Shizuoka then you could get a seven day JR Pass.
However if you want more flexibility and be free to travel to more places than listed above such as Hiroshima etc, then the 14 day pass would be best. It really depends on what you would like visit.
You can find fares and schedules for the trains in Japan using this website, www.hyperdia.com.
Hope that helps.
Best regards
Japan Experience
It is all up to how much you want to spend, and how much time you want to spend in each place.
First off, I advise you strongly not to just "wing it". The more research you do ahead of time before your trip, the less wasted time and fewer blown opportunities to see good place there will be.
As said, your itinerary as is would not pay off for a 14 day JR Pass. If you're willing to add more side trips like Hiroshima, you would see more places and not be as rushed. Naturally it does cost more for the 14 day pass, however. Alternatively with half your time near Tokyo and half near Kansai, you would get even better savings if you squeezed in Hiroshima/Miyajima into a 7 day pass. You only listed about 5 days of travel for going south. Kyoto certainly deserves more attention than just one day - and Nara is worth at least half a day as well. Himeji Castle is not far either and has the best castle in all Japan.
Likewise if you are already seeing Tokyo, you could skip Osaka during the day since it's pretty much a clone of Tokyo. You could see it at night after the Kyoto temples and shrines close down around 5 PM. In Osaka, Dotonbori at night is excellent, and the night views from atop the Umeda Sky Bldg and Abeno Harukas Bldg are stunning. For that saved daytime, you could see Kobe for an afternoon as well as see more in Kyoto.
If you choose to get the 7 day JR Pass, then you could also get a Tokyo Wide Pass for several day trips out of Tokyo. It is easy to reap huge savings from going to places like Izu, Kusatsu, Karuizawa, Nikko, Kamamura etc. If you want to see Mt Fuji, then a day trip to Hakone or the Fuji 5 Lakes area is worth it, and there is a day pass for that as well.
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