From Boston to New York

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Personally, I would take a fairly leisurely broad loop through northern New England and then down the Hudson Valley (very roughly). That would give me the most variety - coast, mountains, history, scenery, etc. - while minimizing the amount of time I'd have to spend in urban congestion, traffic, and heavy beach crowds such as at the Cape. There is certainly plenty to do in northern New England and just some of the sites on the Lake Champlain/Hudson River leg would include a ferry ride on the lake, Fort Ticonderoga, Lake George, Saratoga Springs, and West Point. But of course, this is your trip and your interests may be different.

AZBuck