Captain John Smith and his 14 companions left Jamestown on June 2, 1608 to begin their first exploration of the Chesapeake Bay. They were under orders from the Virginia Company to conduct explorations to evaluate the economic potential of the region and look for sutiable areas for further settlement. The great hope was that the expedition would discover a short, sea-level passage to the Pacific Ocean, a passage that would give English ships easier access to the trade routes in the East and bring great wealth and glory to its discoverers.

The voyage was made in a shallop, a shallow-draft boat roughly 40 ft long that could be sailed or rowed. Although the shallop was probably rather small and uncomfortable for a journey of this magnitude, it was well suited for the task. Captain Smith knew extensive contact with the native people would be necessary so he needed a craft that could be easily landed as well as one in which he could quickly escape if the natives proved to be unfriendly.