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Paris, London, Edinburgh and Dublin in September. Book hotels or wing it?

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I am a Type A planner who would like to book my hotels now for my trip in September. My travel partner and bf of three years has spent more time there and would rather just figure it out once we're there. Should I push him to book now for my peace of mind? I know these are big cities with tons of lodging options so maybe I should just trust him and roll with it. I did read that Edinburgh is packed for festivals in August, but as far as I can tell we should be in a relatively off season (at least compared to summer) if we wait till September. Any words of wisdom would be much appreciated.

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