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Trip itinerary for Tokyo, Hokkaido, and Kyoto - suggestions needed!!

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Here'a our rough plan. We would REALLY like to check out the Izu Shoto islands off of Tokyo but are going to wait until we see the weather forecast (scared off by the tsuyu)

We need a stylish, well-located and comfy hotel in Tokyo, a nice hotel near the train station in Sapporo, and a CHEAP place to crash in Kyoto.

We are considering whether to take the train or fly from Sapporo to Kyoto. We are getting a rail pass so the night train supplement is only a little less cheaper than flying; however, it costs $$ to get from the city center to the airport, plus we need to spend $$ for a hotel

June 25: arrive in Tokyo, 2 PM. Stay in Tokyo
June 26: Tokyo or islands
June 27: Tokyo or islands
June 28: Tokyo or islands. Activate Japan Rail pass; leave at 8 PM on the "Akebono" night train to Aomori
June 29: Aomori to Lake Toya. Stay in Lake Toya (Kohantei)
June 30: Toya - Sapporo to Asahikawa- Asahidake Onsen (Hotel Bearmonte)
July 1: Asahidake and area (Daisetsuzan Shirakaso)
July 2: Leave Asahidake; head to Sapporo
July 3: Sapporo. Take Hamanasu night train (22:00) to Aomori OR Fly from Sapporo to Kyoto
July 4-Head from Aomori towards Kyoto, maybe stop somewhere along the way (depending on weather). Lake Tawazako????
July 4-8 Kyoto (with friends)

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