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I’d suggest a drive from Marblehead ma(absolutely beautiful) to Salem witch city to Beverly Gloucester Manchester Rockport and up the coastal road to Newburyport(MA version of Portsmouth) up to Portsmouth and meander your way to Portland Maine….took my wife’s Irish brother on that trip and he was amazed…. Thought everywhere in USA looked like NYC…. I’d recommend a similar trip up the Hudson valley of NY to lake placid and Saranac…. Also the beauty of a trip from Bennington Vermont to Burlington…..cool towns all along the way… ditto Amherst MA to The Berkshires