Introduced in 1958, the Fiat 500 Jolly retained its hard-working city-car mechanicals—a 479-cubic-centimeter two-cylinder engine mated to a four-speed manual transmission—but whimsical bodywork by Carrozzeria Ghia gave it undeniable charm.

While any Jolly is irresistible, this 1959 United States-market example boasts a remarkable six-plus decades of single-family ownership, during which this special car was used, enjoyed, and restored by members of three subsequent generations.

The initial buyer of this car is said to have purchased it for use as a yacht tender (perhaps taking inspiration from Fiat head Gianni Agnelli, who employed one for that purpose).

Unfortunately, following delivery, he discovered it was too large for his boat.

The Jolly, practically new, was purchased from the frustrated yachtsman by the grandfather of the current consignor.

It soon found a home at the family’s cottage in Virginia Beach, Virginia, becoming an eager companion for their warm-weather activities...