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You'll need at least a week to experience Hokkaido, with a day or two in Sapporo and then a stay in one or two of the places recommended. Distances are large, and a train or road trip across the island takes most of a day. Flying to a regional airport cuts down on unnecessary travel time. Make cars and hotel reservations in advance; outside Sapporo and Hakodate, finding people who speak enough English to do bookings can be difficult. Check on access and weather for each destination when planning a winter trip, when road conditions can be unpredictable and treacherous.