Sharpies are a type of hard chined sailboat with a flat bottom, extremely shallow draft, centreboards and straight, flaring sides. They are believed to have originated in the New Haven, Connecticut region of Long Island Sound, United States. They were traditional fishing boats used for oystering, and later appeared in other areas. With centerboards and shallow balanced rudders they are well suited to sailing in shallow tidal waters.

Sharpies first became popular in New Haven, Connecticut, towards the end of the 19th century. They came into use as a successor to the dugout log canoe and most likely were derived from the flatiron skiff. In an 1879 edition of Forest and Stream, a man named James Goodsell of the Fair Haven neighborhood claimed to have built the first sharpie with his brother in 1848. His claim was never contested. The Goodsell & Rowe Oyster Barn is shown on Front Street in an 1850 Map of Fair Haven which is now in Yale's Beinecke Rare Book and Manuscript Library. That map shows the homes of E.P. Goodsell, J. D. Goodsell, and J. J. Goodsell also on Front Street.

Building Sharpies was a spin-off business from oystering and continued to grow, meeting not only local needs but were sold to other oystermen along the Eastern seaboard. The names of Rowe, Graves and Thatcher became well known as sharpie builders by the 1880s.

Sharpies were typically used for oyster tonging and evolved to suit that work. They grew in popularity because they were easy to row, cheap to build, and fast under sail. They were used for racing. The sailing speed was eleven nautical miles in thirty-four minutes ^{[citation needed]}. By the 1880s nearly 200 sharpies were to be found along the wharves of Fair Haven alone.

Varying in length, the 24–28 ft one-man boats usually had one sail, while the larger two-man boats which were around 35 ft were rigged with two sails, as cat-ketches. They had leg-o-mutton sails with sprit booms on un-stayed masts. The larger boats had three mast-steps; one at the bow, one amidships and one in between. Typically, in the summer, two masts would be stepped: one at the bow and amidships. In the winter, when heavier winds were expected, a single mast would be stepped in between. Their hulls were narrow with a large sheer and low freeboard. At the ends you will find a plumb bow with the heel of the stem sitting just out of the water and a round stern. The centerboard was long and shallow as was the balanced rudder.

The sharpie type migrated south and west to other regions where shallow water prevented deep-draft vessels from operating, including Chesapeake Bay, the Carolinas, the Great Lakes (Ohio) and Florida.

Although most sharpies were rigged as a leg-o-mutton cat-ketch with free standing masts and sprit booms, larger versions – especially those found in the Carolinas and Florida – used stayed gaff schooner rigs which included a jib.

Sharpies were introduced to Florida in 1881, when Commodore Ralph Munroe brought the 33-foot New Haven style sharpie, of his own design, Kingfish to the Miami area of Florida. Perhaps the most famous of sharpies was the Commodore's Egret design, now immortalized in plans available from WoodenBoat magazine. Commodore Monroe designed Egret in 1886 and had her built on Staten Island and delivered to Key West.