Cars and sailing don’t really mix—with a few notable exceptions. One is if you’re talking about something like the Amphicar. And another is the luxury cars that float and waft down the road, aka the land yachts. But while some automakers may dabble in aquatic activities, their cars usually only have a hint of nautical references. However, that’s not exactly the case with the antique car starring in Jay Leno’s latest video: a 1916 Crane-Simplex Model 5 Holbrook Skiff.

Crane-Simplex: Rockefeller’s choice for an American luxury antique car

If you haven’t heard of Crane-Simplex, that’s unsurprising. Like Duesenberg and Wills Sainte Claire, the American automaker has long since shut its doors. However, like those other two brands, when Crane-Simplex was in business, its cars, now antiques, were luxurious, expensive, and highly desirable.

Crane-Simplex formed when two existing automakers, Simplex and Crane, merged in 1915, Hemmings reports. The former was originally an importer of European luxury cars, the National Park Service explains, and started making their own to avoid import duties. And indeed, Simplex’s antique cars offered noticeably higher build quality than other contemporary American cars, RM Sotheby’s reports.

However, by the mid-1910s, Simplex was lagging behind some of its competitors. Mainly because, while its four-cylinder engines offered decent performance, the company didn’t have a six-cylinder engine, Classic Driver reports. But there was another high-end American automaker that did: the Crane Motor Car Company.

Henry M. Crane, a former marine engineer, founded the Crane Motor Car Company. And before he made cars, Crane designed championship-winning speedboats, Bonhams reports. Unfortunately, while Crane’s cars offered luxury and performance, they didn’t sell well, Bonhams reports. However, Simplex, wanting his expertise, bought Crane’s company and his service. Thus, Crane-Simplex was born.

Like most antique car companies, Crane-Simplex didn’t make cars with bodies. Instead, the automaker sold its customers, which included the Vanderbilt and Rockefeller families, a bare chassis with a powertrain, ClassicCars.com explains. Then, like Bentley’s and Rolls-Royce’s clients back then, the customer went to a coachbuilder to make a custom body and interior.

And in the case of the 1916 Crane-Simplex Jay Leno owns, that custom body was inspired by boats.

Jay Leno feels like “the captain of a ship” behind the wheel of his 1916 Crane-Simplex Model 5 Holbrook Skiff

The antique car featured in Jay Leno’s video is ‘1916 Crane-Simplex Model 5 Holbrook Skiff.’ Holbrook is the coachbuilder who designed and made the body for this particular car. And the ‘Skiff’ part is from its inspiration source.

It has a propeller mounted on the rear spare wheel and air intakes shaped like ship ventilation pipes. To get inside you enter in from the side like on a speedboat. And like a high-end boat, the interior features leather, mahogany, and teak.

While the 1916 Crane-Simplex Model 5 is an antique car today, for its time it offered decent performance. Under the hood is a 9.2-liter inline-six engine that Jay Leno claims makes 110 hp, linked to a four-speed manual. And incredibly, Jay Leno still runs the original spark plugs from 1916.

This antique car has been restored twice, though it’s 100% original. The only modern-day part is the battery. It lacks front brakes, you operate the throttle by hand, and the interior clock is hand-wound.

Interestingly, this 1916 Model 5 has a built-in air compressor to reinflate the tires in case of a puncture. But apparently, that isn’t an uncommon sight on antique cars of this vintage. And given that most roads back then weren’t paved, it makes some sense. Plus, the engine block was cast as two separate inline-three blocks. This technique was likely a way to avoid wasting time having to re-cast an entire six-cylinder block, Hagerty explains.

‘Land yacht’ is a good appellation for this antique car. Jay Leno describes it as “an actual yacht that I’m driving on land.” Considering it only has rear brakes, it stops reasonably well. The engine, while not terribly powerful, is “a torque monster,” Leno says. And the interior is “just beautifully done,” he says. Little wonder some called Crane-Simplex the American Rolls-Royce.

Be prepared to pay if you want to sail the road

Getting behind the tiller—sorry, wheel of a Crane-Simplex wasn’t easy. When Jay Leno’s car was new it cost $10,000. That’s as much as 16 Ford Model Ts, Hagerty reports, and the modern equivalent of $241,300.

Antique Crane-Simplex cars rarely come up for sale due to their relative rarity. And when they do, they typically command prices in the $100,000-$200,000 range. Though that’s still cheaper than a Riva Aquarama.

Follow more updates from MotorBiscuit on our Facebook page.