Travelling around Japan by yourself (ie without a package tour) is really not as difficult as people seem to think it is. If you're sticking to the key tourist areas such as Tokyo, Kyoto and Osaka, there's tons of information online, its pretty easy to manage all the hotel bookings and even transportation. Quite a lot of the train station names are marked in Ryomanji, and even if you do get lost, the Japanese are very friendly people who would go out of their way to get you back on the right track.
Getting to Hokkaido from Singapore is slightly more difficult because there are no direct flights. SQ was supposed to start one last year, but due to the economic situation, they decided not to after all. So getting to Hokkaido means either taking a domestic flight or the Shinkansen.
Internal flights are extremely expensive if you try to book them independently, and a one-way 1h flight may cost you as much as S$400! If your international flight is JAL or ANA, prices drop about 50% if you do the booking together. Alternatively, you can fly one of the "budget" airlines such as Skymark from Haneda. This is a little of a hassle because you would need to have a 45min bus transfer from Narita to Haneda, but at least the fare is about 25-50% cheaper. The Shinkansen is a cheaper option, but it take a full day and the departure time doesn't match with the morning arrival for the international flight. So its not really time efficient unless you want to spend a day in Tokyo before heading up north.
The first time we went to Hokkaido, we stayed 1 day in Tokyo before taking a full day train trip up the next day. The second time however, efficiency in use of time was preferred, so we ended up flying over on a low cost airline via Haneda. For the return legs, usually we want to do intensive last minute shopping of seafood (cooked and nicely packed in a styrofoam box with ice packs to help it last the trip back to Singapore) at the New Chitose Airport, so we fly direct from there to Narita on the more expensive JAL or ANA.
To be continued...
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