Wheeler Launches an Inspired Head-Turner in Brooklin

Photos by Billy Black

Syntax takes full advantage of the latest systems, including twin 1,000-hp MAN diesel engines, giving it a cruising speed of 25 knots.

Ernest Hemingway is long gone, and his famous sportfishing boat, Pilar, was laid to rest decades ago at his former home in Cuba. But the spirit of the American author and his beloved boat lives on in the form of Wheeler Yacht’s new vessel, the Wheeler 55. The boat was launched in July, 2024, at Brooklin Boat Yard and captures the look and nostalgia of Pilar, as well as of a bygone era of distinctive wooden yachts that turned heads wherever they cruised.

The Wheeler 55, named Syntax, is all about style, performance, and luxury. It was built with the panache of Pilar, with a mahogany plywood hull using cold-molded construction techniques, laminated Douglas fir structural elements, a sipo mahogany cabin and interior, and all-teak decks.

The latest Wheeler launch oozes luxury throughout, from its plush cushions and the sipo mahogany cabin down to the captain’s chair and wheel in the wheelhouse.

For Wheeler Yachts, Syntax represents the latest chapter in the company’s storied history. The original yard was founded in Brooklyn, New York, in 1910 by Howard Wheeler, who turned it over to his five sons when he retired in 1957. Known for its high-quality, hand-crafted boats, Wheeler Yachts built nearly 4,000 vessels until it went out of business in 1965.

Its best-known boat style was called the Playmate, and its best-known customer was Ernest Hemingway; a Wheeler Playmate also served as the S.S. Minnow in the opening credits of the 1960s TV show “Gilligan’s Island.” When Hemingway bought his 38-foot boat in 1934, he had it customized to include a flybridge, a live fish well, a lowered sheer line, a fighting chair from which he fished, and a wooden roller across the transom to help haul fish aboard. The boat had extra-large fuel tanks so he could stay at sea longer and two motors, a 75-hp for traveling and a 40-hp for trolling. He named it Pilar, the nickname for his then-wife Pauline and later the name of the heroine in his 1940 book For Whom the Bell Tolls.

The Wheeler 55, pictured here in this night shot, was inspired by the company’s 56-foot Playmate model of 1931. That vessel solidified the legacy of the original Wheeler Shipyard Corp., which built more than 4,000 vessels from 1910 to 1965.

Syntax is hull No. 1 of the 55-foot model, said Wes Wheeler, the great-grandson of Howard Wheeler, who has reincorporated the company. While standing inside the cabin of the vessel, Wheeler said he hopes the boat is just the first of many Wheeler 55s to come.

When Wheeler relaunched the company, he had Brooklin Boat Yard build him a 38-foot model with the same dimensions and look as Hemingway’s boat, but with modern technology and luxurious accommodations. That boat, Legend, was launched in 2020 and calls Hilton Head, South Carolina, its home. Wheeler, who is retired from a long career as an executive in the pharmaceutical industry, regularly cruises the Maine coast on Legend.

Wheeler said Hemingway would have been proud of Legend, carrying on the tradition of Pilar.

As for the Wheeler 55? “I think he’d be blown away,” Wheeler said.

Syntax is filled with top-of-the-line appliances, including a Breville espresso maker, a Kenyon cooktop, and a Vitifrigo wine cooler. The guest suite is located in the aft section of the vessel. The boat also has sleeping quarters for crew members. The master stateroom is in the bow section of the boat. Both the master and guest staterooms have their own heads and showers.

The tender is kept on top of Syntax’s cabin. Beyond having the style of the traditional Wheeler boats, the Wheeler 55 is powered by twin 1,000-hp V8 MAN engines, giving it a cruising speed of 25 knots and a range of 300 miles. It also has synchronized joystick controls, with bow and stern thrusters, and Seakeeper and Zipwake stabilizer systems for smooth and stable rides.

Under the deck, it has two luxurious sleeping staterooms with heads and showers, as well as a cabin for the boat’s crew members. Its galley has a refrigerator and freezer, a wine cooler, a microwave, and an espresso machine. For added comfort, it has central air conditioning, a top-of-the-line stereo, and a washer and dryer. As a finishing touch, its wheel is an exact copy of the wheels that were used by Wheeler Yachts back in its heyday nearly a century ago.

“We didn’t skimp on anything,” Wheeler said. “Everything is top of the line, from the hardware to the silverware.”

The buyer and the sales price aren’t being disclosed, but the hailing port, as painted on the transom, is Oak Island, off Boothbay.

Wheeler said he hopes Syntax is just the first Wheeler 55. Parts for the next one—hull No. 2—have already been ordered and he plans to have it built and find a buyer in the next couple of years. He expects the sales price to be in the $5.5 million to $6 million range.

Syntax was was built and launched at Brooklin Boat Yard. It took 19 months and 65,000 man-hours to build it to completion.

Wheeler’s decision to bring Wheeler Yachts back to life is tied directly to Hemingway. Wheeler, 67, never worked in his family’s yacht business, but was drawn in when filmmakers who were working on a script about Hemingway’s life in Cuba approached him looking for a replica of Pilar for a movie they were making. The movie was never made, but Wheeler was so inspired by the replica he found that he decided to bring the company back to life. 

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Clarke Canfield is a longtime journalist and author, and lives in South Portland.

Wheeler 55 Specifications

LOA:  55' 5"
LWL:  54' 7"
Beam:  16' 9"
Draft:  4' 6"
Displacement:  60,000 lbs.
Cruising speed:  25 knots
Range at cruising speed:  300 miles
Power:  2 x MAN V8-1000

BUILDERS
Wheeler Yacht Company
Chapel Hill, NC
www.wheeleryachts.com

Brooklin Boat Yard
Brooklin, ME
www.brooklinboatyard.com

REVERSE ENGINEERING
Bill Prince Yacht Design
Port Washington, WI
www.billprinceyachtdesign.com