The work functions of the pilot go back to Ancient Greece and Roman times

The work functions of the pilot go back to Ancient Greece and Roman times, when locally experienced harbour captains, mainly local fishermen, were employed by incoming ships' captains to bring their trading vessels into port safely. Eventually, in light of the need to regulate the act of pilotage and to ensure pilots had adequate insurance, the harbours themselves licensed pilots.

Although licensed by the harbour to operate within their jurisdiction, pilots were generally self-employed, meaning that they had to have quick transport to get from the port to the incoming ships. As pilots were often still dual-employed, they used their own fishing boats to reach the incoming vessels. But fishing boats were heavy working boats, and filled with fishing equipment, hence a new type of boat was required.

Early boats were developed from single-masted cutters and twin-masted yawls, and later into the specialist pilot cutter. These were effectively light-weight and over-powered single masted boats with large steeply angled keels, making them deep draft under power and shallow draft in lighter sail.

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