If I want to visit Japan for two weeks with wife and toddler…

1) Best month to visit to balance good weather and cost?

2) Best 2 cities to stay that are family friendly?

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for a first timer I’d say Tokyo and Osaka (you can make day trips to Kyoto and Kobe easily). Avoid cherry blossoms and go to see autumn leaves instead, equally beautiful and def less tourists. What kind of activities are you into when traveling? That could also influence the itinerary.