Wheeler 38 Playmate

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Illustration by Jim Ewing

Illustration by Jim Ewing

If you wanted to buy a rugged, seaworthy motor cruiser in the mid-1930s, a Wheeler was a good choice. Howard E. Wheeler’s shipyard in Brooklyn, New York, had been in business since 1910, turning out everything from skiffs to larger power yachts.

The 38-foot Wheeler Playmate was popular as a sport boat and family-friendly cabin cruiser. Built with mahogany planking on oak frames, it had an easily powered hull with a modest 12-foot beam. The cockpit was open, and the helm station was to starboard inside a protected wheelhouse with room for gear and charts. The trunk cabin’s design added headroom below, where the layout might include a stateroom forward, an enclosed head and a galley.

In 1934, the American novelist Ernest Hemingway, fresh from an African safari, picked up his brand-new Wheeler 38 in Miami. He named it Pilar, after his wife, and drove it south to his Key West home—and into history.

Pilar was modified to go after big game such as marlin and tuna in the Caribbean. He had the Wheeler yard install a livewell and outriggers, cut down the transom to accommodate a roller for hauling aboard fish, and ordered a four-cylinder trolling engine with an offset prop shaft. (A flybridge came later.) Power came from a six-cylinder, 75-hp Chrysler Crown Marine inboard gas engine, giving the boat a 15- to 16-knot cruising speed. (Other 38s had twin engines.)

Hemingway won tournaments in the Florida Keys, Cuba and the Bimini area of the Bahamas, catching seven marlin in one day in 1938. His exploits often found their way into his books and stories, and he still owned the boat at the time of his death.

The original Pilar is now on display in Cuba. After building more than 3,500 boats, the Wheeler Shipyard Corporation laid its final keel in 1966. Today, a Wheeler descendant is bringing the 38 Playmate back to life with modern technology. Some say Hemingway would be pleased. 

This article originally appeared in the October 2019 issue.