Navigating large ships past the sandbars and shallows of the Delaware was always a difficult task. After Philadelphia was founded in the 17th century, deep water captains began to hire Lewes pilots, whose knowledge of the local waters enabled them to guide vessels to the City of Brotherly Love.
In the 19th century, pilots were organized into small groups who purchased schooners that normally carried six pilots. These picturesque sailing vessels cruised the waters off Cape Henlopen for a week at a time in search of ships needing a pilot.
When a vessel was sighted, the pilot schooner sailed to within a short distance of the ship, and a skiff carrying the pilot rowed over to the ship.