Written By: Eliza Berman

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 captions in the story read as a cheeky how-to manual.

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 edited this gallery for LIFE.com. Follow her on Twitter @lizabethronk.

Nelson Rockefeller family on vacation in 1958

Polish the 1931 Model A Ford.

Alfred Eisenstaedt The LIFE Picture Collection/Shutterstock

Nelson Rockefeller family on vacation in 1958

Check the convertible cover in case of rain.

Alfred Eisenstaedt The LIFE Picture Collection/Shutterstock

Nelson Rockefeller family on vacation in 1958

Ensure that even the youngest family members adhere to the unofficial dress code of collared shirts.

Alfred Eisenstaedt The LIFE Picture Collection/Shutterstock

Nelson Rockefeller family on vacation in 1958

Build a pool with ocean views.

Alfred Eisenstaedt The LIFE Picture Collection/Shutterstock

Nelson Rockefeller family on vacation in 1958

Pose for treasured family photos.

Alfred Eisenstaedt The LIFE Picture Collection/Shutterstock

Nelson Rockefeller family on vacation in 1958

Get the sails ready for the open waters.

Alfred Eisenstaedt The LIFE Picture Collection/Shutterstock

Nelson Rockefeller family on vacation in 1958

Wait for a nice and windy day to take out the boats.

Alfred Eisenstaedt The LIFE Picture Collection/Shutterstock

Nelson Rockefeller family on vacation in 1958

Ensure that at least one person on the sailboat knows how to sail.

Alfred Eisenstaedt The LIFE Picture Collection/Shutterstock

Nelson Rockefeller family on vacation in 1958

Get tennis rackets restrung for games on the private courts.

Alfred Eisenstaedt The LIFE Picture Collection/Shutterstock

Nelson Rockefeller family on vacation in 1958

Ensure clay courts are swept and ready for a game.

Alfred Eisenstaedt The LIFE Picture Collection/Shutterstock

Nelson Rockefeller family on vacation in 1958

Engage in family pastimes that bring generations together.

Alfred Eisenstaedt The LIFE Picture Collection/Shutterstock

Nelson Rockefeller family on vacation in 1958

Ensure that grounds are well-manicured and decorated.

Alfred Eisenstaedt The LIFE Picture Collection/Shutterstock

Nelson Rockefeller family on vacation in 1958

Bring along a famous LIFE photographer to document lazy summer days.

Alfred Eisenstaedt The LIFE Picture Collection/Shutterstock

Nelson Rockefeller family on vacation in 1958

Make time for oceanside chats in the salty, fresh air.

Alfred Eisenstaedt The LIFE Picture Collection/Shutterstock

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