Sail Away with the Iconic Covers of the New Yorker

Over the past nine decades, the New Yorker has featured dozens of covers inspired by sailing and the sailing lifestyle.

The New Yorker is known for their fantastic, iconic, and often controversial illustrated covers, from the first issue on February 21, 1925 depicting dandy Eustace Tilley created by Rea Irvin, which would become the magazine’s logo for the 90 years since, to the October 17, 2011 cover showing Steve Jobs facing the pearly gates.

The magazine’s cover has showcased political foes and sports heroes, racial tensions and fast food restaurants, New York taxicabs and Putin on ice skates. The cover is not meant to reflect a particular story in the magazine but rather represent the culture as a whole.

“What I’m really looking for are ideas that come from the artists on topics that will give us a sign of the era that we live in and, as a collection of images, will collect a picture of our time,” Françoise Mouly, the New Yorker’s art editor since 1993, told

Over the years, the New Yorker has had several covers featuring sailboats and sailing, most recently, the May 9, 2016 “Regatta on the Hudson” by artist Bruce McCall inspired America’s Cup.

New Yorker sailing Bruce McCall

“Regatta on the Hudson” by Bruce McCall.

“Those new racing boats are hard to paint. I had the idea originally when I thought boats were just boats. But I like to paint skylines all the time, whether there are boats or not,” he said of the image.

Here we showcase some of our favorite New Yorker covers featuring sailing and sailboats over the past nine decades.

Istvan Banyai Aug 29 2011

“On the Horizon” by Istvan Banyai.

“On the Horizon,” August 29, 2011, by Istvan Banyai. Banyai says that seeing a big expanse or water is “soothing, calming, relaxing. It brings you positive feelings, even if you’re stressed out. Even if you live in New York.”

Drawing While Waiting Jacques de Loustal

“Drawing While Waiting” by Jacques de Loustal.

“Drawing While Waiting,” April 18, 2011, by Jacques de Loustal. The Parisian artist was inspired by Italy’s Amalfi Coast to capture what he calls a moment of “pure contemplation while you are sitting somewhere beautiful.”

garrett price new yorker covers

New Yorker covers by Garrett Price.

Artist Garrett Price is one of the New Yorker’s most prolific creators of covers featuring sailing. On the August 7, 1954, cover (left) Price shows people on a small sailboat with a tall sail try to alert the bridge operator to raise it before it’s too late.

New Yorker Cover Jacques de Loustal

“Back in the New World” by Jacques de Loustal.

“Back in the New World,” October 11, 1993, by Jacques de Loustal. The drawing shows a sailboat with patched sails making its way into the New York harbor against the backdrop of the World Trade Center.

on the move jacques de loustal

“On the Move” by Jacques de Loustal.

“On the Move,” April 21, 2008, by Jacques de Loustal. Created for the “Journey’s issue, this is the middle frame of a three-part cover showing an adventurous couple inappropriately dressed for the environment.

New Yorker Covers Arthur Getz sailing

New Yorker covers by Arthur Getz.

Arthur Getz was the most prolific of New Yorker illustrators having created more than 200 covers during his career, many of which had a sailing theme.

new yorker sailing covers

Covers by Gretchen Dow (left), Arnie Levin (center), Garrett Price (right).

new yorker covers sailing charles martin

New Yorker covers by Charles Martin.

Garrett Price Charles martin sailing

Covers by Garrett Price (left and center) and Charles Martin.

There are dozens more of New Yorker covers with sailing and sailboats. Which are your favorite? Tell us in the comments!

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