Hello! I plan on going to Hokkaido and travel all the way down to Okinawa, visiting as many prefectures as I can along the way in approximately 90 days. Should I buy three Japan rail passes then? By the time I activate the third one, wouldn't it already be invalid? Please enlighten me and tell me my best option. Thank you in advance.
In terms of timing, you could do so. A JR Pass needs to be activated within 3 months after issue date. At time of activation, you can select a starting date up to 30 days ahead of time. So effectively you could have up to 4 months to start your travel. Assuming you are in also finishing in Okinawa where there are no JR lines, I think you'll be fine using 3 passes with a bit of planning.
All the best,
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