The Enterprise was designed by Jack Holt in 1956 for The News Chronicle during the post-war sailing boom, becoming the first UK sailing dinghy to be sponsored by a national newspaper (followed in due course by the Mirror Dinghy, also designed by Jack Holt).

Adopted by many sailing schools, the Enterprise's combination of size, weight, and power has widespread appeal.

They are also relatively unstable in comparison with other dinghies of similar performance, they have handling characteristics which would generally be associated with much faster designs.

The first two Enterprises built were sailed from Dover to Calais both as a test and for advertising purposes.

This feat was repeated on the Enterprise's 50th anniversary, but this time the two boats not only sailed to France, but also returned to England.