The Jolly was the brainchild of Fiat chairman Gianni Agnelli, who desired a small car that could be carried aboard his 82-foot ketch, Agneta, and be easily lowered over the side for local transportation at various Mediterranean ports of call.

Agnelli’s yacht tender, an open-air 500 with wicker seats, cut-out doors, and a fringed surrey top, proved so popular that it was put into limited production by Italian coachbuilder Ghia.

Through the Jet Age, it was the vehicle of choice for the well-heeled at the world’s most fashionable resorts.

It retained the Fiat 500’s hard-working city-car mechanicals—a 479-cubic-centimeter two-cylinder engine mated to a four-speed manual transmission—but its whimsical bodywork (and name)—gave it undeniable charm.

While any Jolly is special, U.S.-spec versions—denoted by their larger “frog eye” headlights—such as the example offered here, are even more so, because they were produced in limited numbers.

This Jolly is said to have been purchased by its fi...