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When the question is how to vacation like a Rockefeller, the quick answer is to rewind history to about 1870 and found the largest oil refinery in the world. Short of that impossible task, however, it’s possible to take some hints from these photographs of Nelson Rockefeller and his family on vacation in Seal Harbor, Maine, in 1958.
The images by Alfred Eisenstaedt accompanied a story about that year’s New York state gubernatorial election, in which voters faced a “Choice of Millionaires.” Rockefeller, who would go on to unseat W. Averell Harriman, was on vacation at his family’s estate near Acadia National Park—a park that, thanks to the family’s commitment to philanthropy and conservation, exists largely due to Nelson’s father, John.
When planning your own Rockefeller-inspired vacation, be sure to dress your family in collars and cardigans, polish the 1931 convertible Model A Ford, check that everything’s shipshape on the sailboat and lay down new clay on your private oceanside tennis courts. Oh, and bring along one of LIFE Magazine’s most famous photographers to document it for posterity.
Liz Ronk, who edited this gallery, is the Photo Editor for LIFE.com. Follow her on Twitter @lizabethronk.