Various types of watercraft used in Colonial Virginia have been mentioned in the records. The dugout canoe of the Indians was found by the settlers upon arrival, and was one of the chief means of transportation until the colony was firmly established. It is of great importance in the history of transportation from its use in pre-history to its use in the world today. From the dugout have come the piragua, Rose's tobacco boat, and the Chesapeake Bay canoe and bugeye as we see them today.

The first boats in use by the colony in addition to the Indian canoe were ships' boats—barges, long-boats, and others. A shallop brought over in sections was fitted together and used in the first explorations. As the years went by, however, "almost every planter, great and small, had a boat of one kind or another. Canoes, bateaux, punts, piraguas, shallops, flats, pinnaces, sloops, appear with monotonous regularity in the seventeenth and eighteenth century records of Virginia and Maryland."

Little is known about the construction of boats in the colony except the log canoe. A long and thick tree was chosen according to the size of the boat desired, and a fire made on the ground around its base. The fire was kept burning until the tree had fallen. Then burning off the top and boughs, the trunk was raised upon poles laid over crosswise on forked posts so as to work at a comfortable height. The bark was removed with shells; gum and rosin spread on the upper side to the length desired and set on fire. By alternately burning and scraping, the log was hollowed out to the desired depth and width. The ends were scraped off and rounded for smooth navigating.

Captain John Smith, who had a number of occasions to use the canoe, wrote that some were an elne deep (forty-five inches), and forty or fifty feet in length; some would bear forty men, but the most ordinary were smaller and carried ten, twenty, or thirty men. "Instead of oars, they use paddles or sticks with which they will row faster than our barges." Additional space and graceful lines in the canoes were secured by spreading the sides. To do this, the hollowed log was filled with water and heated by dropping in hot stones until the wood became soft enough to bend into the desired shape by forcing the sides apart with sticks of different lengths and allowed to harden.

The tools with which the Indians built their boats and used for other purposes, were tomahawks of stone sharpened at one end or both, or one end was rounded off for use as a hammer. A circular indentation was made in the center to secure the tomahawk to the handle. Another method of fitting the stone tomahawk to a handle was to cut off the head of a young tree, and as if to graft it, a notch was made into which the head of the hatchet was inserted. After some time, the tree by growing together kept the hatchet so fixed that it could not come out. Then the tree was cut to such a length as to make a good handle. Another method in use was that of binding the stones to the ends of sticks and gluing them there with rosin.

Some colonists did not hesitate to take the canoes from the Indians, which they may or may not have returned. On one occasion the King of Rappahanna demanded the return of a canoe, which was restored. Among the first laws of the General Assembly was that for the protection of the Indians, enacted in August, 1619: "He that shall take away by violence or stealth any canoe or other things from the Indians, shall make valuable restitution to the said Indians, and shall forfeit, if he be a freeholder, five pounds; if a servant, forty shillings or endure a whipping."

A story of an Indian and his canoe was told by John Pory, Secretary of Virginia, after he had visited the Eastern Shore. "Wamanato, a friendly Indian, presented me with twelve bever skins and a canow which I requited with such things to his content, that he promised to keep them whilst he lived, and berie them with him being dead."

Several writers of boatbuilding have expressed the thought that the evolution of the Chesapeake Bay canoe and the Chesapeake Bay bugeye from the Indian dugout canoe was one of the most interesting developments in the history of shipbuilding. M. V. Brewington, in his Chesapeake Bay: A Pictorial Maritime History, says of this development: "The white man's superior knowledge of small craft soon indicated changes which would improve the canoe: sharp ends would make her easier to propel and more seaworthy; broader beam and a keel would increase stability; sail would lessen the work of getting from place to place. Sharpening the bow and stern was a simple matter; the increased beam was difficult because no single tree could provide the needed width. In time, the settler learned to join two or more trees together to give the beam desired. He learned how to add topsides, first of hewn logs, later of sawed plank. A keel was added and a sailing rig. After the centerboard was invented, it took the place of a keel…."

"But the culmination of the simple, single log, trough-shaped Indian dugout was the bugeye, a complex vessel as much as eighty-five feet in length. There was an intermediate step between the canoe and the bugeye, the brogan, a large canoe, partially decked, with a cuddy forward in which a couple of men could sleep and cook…. The earliest known use of the name "bugeye" was in 1868, but doubtless the word was not coined upon the first appearance of the vessel itself…. In essence the bugeye was a large canoe, fully decked, with a fixed rig following that of the brogan. There were full accommodations for the crew which, because the vessel was built for oyster dredging, needed to be comparatively large…. Throughout the course of development from canoe to bugeye, the original dugout log bottom was always apparent in this most truly American craft."