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When is it better to activate the pass on the following itinerary?

Hi - Our trip is 25 days starting on day 1 from New Chitose airport to Sapporo - Asahikawa - than continuing by train on day 5 onward -Asahikawa - Hakodate - Tokyo- Matzumoto - Kanazawa - Kyoto - Naoshima - Hiroshima -Hakone -Tokyo and I don't know whether to activate my Pass on the 1 st day travelling Sapporo - Asahikwa or buying a one way ticket and activating the pass only on the 5 day from Asahikawa to Hakadote - Tokyo- so the pass will last till my return trip from Hiroshima to Tokyo ? could you help me with this ? many thanks Di

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    It's hard to say anything without more info. How many days are you staying in each place? What kind of JR Pass are you planning to use?
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    Hi again : our Itenerary of 21 goes as follows:
    7/10 New Chitose- Asahikawa- 3days car rental.
    On the 11/10 Asahikawa- Sapporo - Hakadote
    12/ 10 we thought to take the Shinkansen to Tokyo;
    12-17/ Tokyo
    17/ Tokyo -Matsumoto -train than car rental for 3 days from Matsumoto
    20/ 10 Kanazawa - Kyoto
    20-25 Kyoto
    25/10 Kyoto - Naoshima
    27/ Naoshima - Hiroshima
    28/ Hiroshima - Hakone or Hiroshima -Tokyo
    29-31 Tokyo
    Leaving from Haneda on the 31/10
    So my question is whether to take a 21 days pass and if so- where to activate it? On the 7/10- so it will end before my return trip to Tokyo or on the 11/ 10
    Many thanks for your help!
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    Hi,
    Well a 21 day pay would pay off handsomely for your plans. You can activate it either when you arrive at Chitose or in Asahikawa, but you should activate it to be able to start using it from Oct 11. You don't have to start using it immediately when you turn in your voucher for the actual pass - you can set a future date as your first day. And if you will rent a car during your first few days, it'd be a waste to have an active unused pass with the clock running.

    A few notes however. For the car rentals, if you don't return the car at the same place you rented it from, there can be some pretty stiff drop off charges.
    Also you are putting in way too much time for Tokyo. About 3-4 days is enough, and for the rest of the time, you can add even more value into your pass by taking some good day trips to places like Nikko, Kamakura, Izu, Kusatsu, the Hitachi Seaside Park, etc. Hakone and the Fuji Lakes are also good, but you should use a separate pass for there:
    http://www.odakyu.jp/english/deels/
    http://www.japan-guide.com/e/e5200.html
    http://www.japan-guide.com/e/e6900.html
    Also for Kyoto, you should put in at least half a day to see Nara as well. If you really want to cover the area, you could also take half a day to see Himeji, with Japan's finest castle, and see Kobe in the evening on the way back.
    Since you are already seeing Tokyo, you can largely skip Osaka during the day. After the temples of Kyoto close down around 5PM, you can zip over to Osaka for the evening. At night the city comes alive and has some great places to see, such as Dotonbori, plus the night views from the Umeda Sky Bldg and Abeno Harukas Bldg are wonderful.
    Also note that the Pass does not cover the ferry from Uno to Naoshima.
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    Thank you so much Tenjin for your help and excellent suggestions!! -
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