Having seen several of the castles Japan has to offer, I can say Matsumoto Castle is one of the more picturesque of the bunch. It is shrouded in lots of interesting history which you can learn about when taking a tour inside. Tours are free and English guides are on hand which is a great service but you can pick up much of the history from information boards in each area of the castle which almost doubles as a museum in some areas. The only advice I can give is to avoid the weekends if possible. I visited on a Sunday and half way into the castle there was bottleneck of tourists, turning a 20-30 minute tour into a 1 hour tour. Also, like many other temples and castles in Japan, the course is linear and can't be backtracked, so if you do go on a weekend or public holiday, expect to deal with large crowds. On the whole though, Matsumoto Castle is a beautiful landmark that should not be missed if you are heading to or from the highlands!
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