If our itineraries starts from Tokyo to Hakkaido/Sapporo, then we plan to go Osaka and Kyoto, may I know what rail pass you suggest us to buy? The trip is about 15 days.
If you want to take the bullet train from Tokyo to Sapporo, then back and through to Kansai, you could certainly make a 14 day JR Pass pay off handsomely. But from Tokyo to Sapporo is nearly 8 full hours, and back down to Kansai about 11 hours - completely murdering the day. If I were you, I'd fly using a low cost carrier like Jet Star, Vanilla Air, or Peach. A one way ticket can be as low as ¥5000 one way, and you get there in about 2 hours. Or ANA's Experience Japan Fare is ¥10,800 each way. You can use some other rail passes around the Tokyo area or Kansai area if you will be going around to see the sights.
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