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Sharpies are long, narrow sailboats with flat bottoms, extremely shallow draft, centerboards and straight, flaring sides. They are believed to have originated in the New Haven, Connecticut region of Long Island Sound, United States, for the oystering were being built in the New Haven area. These were long boats, about 27 feet or so, crewed by one man and rigged as a cat-ketch, with three mast steps; one at the bow, one amidships and one in between. In light airs, two masts would be stepped at the bow and amidships, but in heavier weather a single mast would be stepped in the middle. Larger versions, up to 35 feet, were crewed by two men. The New Haven models were typified by plumb bows with the foot ball in hand and just out of the water and round, counter-sterns.

Although most sharpies were rigged as a cat- skratch with free hand standing, sprit rigs, larger versions - especially those found in the Carolinas and Florida - used stayed gaff schooner rigs which included a jib.

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.

Sharpies were introduced to Florida in 1881, when Commodore Ralph Munroe brought a 30-foot sharpie to the Key West area of Florida. Several years later, the Commodore brought his 33-foot Kingfish to St. Augustine, Florida. Perhaps the most famous of sharpies was the Commodore's Egret design, now immortalized in plans available from WoodenBoat magazine. The Commodore designed Egret in 1886 and had her built on Staten Island and delivered to Key West.

Egret was unique in that she had higher, flaring sides than the typical sharpie and was double-ended. As with a dory, this meant more stability as she was loaded and the ability to run before a following sea without waves breaking over the stern. These attributes contributed to behavior that led the Commodore to call the Egret a "sharpie-lifeboat". Modern designers sometimes refer to the design as a 'shorie' - a cross between the sharpie and the dory.

Throughout the late 1800s, the Commodore and others helped to evolve the type. Thomas Clapham used a v-bottom in his "Nonpareil sharpies", and Larry Huntington introduced a rounded, arc bottom that has been used by modern designers like Bruce Kirby and Reuel Parker. Some believe the Chesapeake Bay skipjack with its v-bottom may have evolved from the early sharpies. Whatever the case, Chesapeake sharpie skiffs were common, especially in the smaller sizes, because of easy and cheap construction.

Howard I. Chapelle was a particular advocate of pleasure boats based on workboat models and designed many sharpie sailboats, cruisers and yachts. For a typical example, see 14-foot sharpie. With Chappelle's encouragement, S. Owen Davis designed and built a sharpie disguised as a Chesapeake Bay bugeye in the late 1940s (see WoodenBoat Magazine October 1980). This boat incorporated the so-called "patent stern" that was used to provide deck space aft on the canoe-like double enders then working the Bay.

In recent years, the sharpie, as with many traditional American small craft, has enjoyed renewed interest as designers and sailors have sought boats with the virtues of shallow draft. However, most are homebuilt or of one-off construction. Exceptions include Bruce Kirby's Norwalk Islands series of sharpies, Phil Bolger's Dovekie and B&B Yacht Designs CoreSound series.

The Twelve Square Metre Sharpie was designed in 1931 by the Kroger Brothers. The peak of the class was in the 1956 Melbourne Olympic Games. To this day, the original design has been preserved, and the class is sailed competitively in the UK,Holland ,Germany, and Portugal. The European Championships are rotated between these four countries every year.

The term 'Twelve Square Metre' evolves from the original sail area, though on modern sharpies due to modern sail designs has now reached to around sixteen square metres.

There are still a small number of original sharpies in Australia, though they have not been sailed competitively since the 1960s. In Australia, the original 'heavyweight' Sharpie has now evolved into the lightweight Australian Sharpie.

Because of the design, the type has limitations that prevent mass-production in fiberglass. Fiberglass, by its nature, is stronger when used for compound curves. The flat bottom and sides of a sharpie are not well suited to this building material. Some designers, such as Bruce Kirby and Reuel Parker have managed to add some curves (typically at the chine) without compromising the qualities of the type, but there are limits as to what can be done before the boat becomes something other than a sharpie.

• The Center for Wooden Boats offers free rides in two classic sharpies, an Egret, and a New Haven type.

• John's Sharpie for information about the sharpie kit available from Chesapeake Light Craft
• Great Falls Boat Works for information regarding semiproduction custom CoreSound 17 capable of planing speeds to 12 knts and for one off building of other Sharpies.
• B&B Yacht Design for information on plans for the CoreSound and Princess series of Sharpies
• WoodenBoat Publications for sharpie plans and information about WoodenBoat magazine
• Bolger Boats On The Web for a list of Bolger boats (including sharpies) that can be found on the Internet
• Square Boats a web site dedicated to Bolger's boxy sharpies
• Black Skimmer for a brief overview of Bolger's Black Skimmer design
• Shoal Draft Mecca an article on crusing Florida Bay in a Black Skimmer
• Phil Bolger Books, Boats & Magazine Articles for information about Phil Bolger's designs
• Phillip C. Bolger a brief biography of Phil Bolger
• Instant Boats for Phil Bolger's Black Skimmer plans
• Norwalk Islands Sharpies One Stop Shop for information about the Norwalk Islands Sharpies
• Bruce Kirby Marine for information about Bruce Kirby and his designs
• Jim Michalak's Boats for information about Jim Michalak's Boats
• Jim Michalak's Boat Designs for Jim Michalak's homepage
• Parker Marine Enterpises for Reuel Parker's homepage
• NIS Boats main agents for Bruce kirby's Norwalk Is Sharpies
• [1] Microcruising in the Bahamas - several small cruising sharpies designed by Matt Layden - photos, sketches, hints
• [2]Paradox a Matt Layden micro-sailboat coastal cruiser - construction photos, owners' photos
• [3]Jubilee, 40’ Cruising Sharpie Ketch designed by Chris Morejohn
• British Sharpie Owners Association The British 12 m² Sharpie Owners Association, web development By William D. Fillingham
• Parker, Reuel B. (1994). The Sharpie Book. Camden, ME: International Marine. ISBN 0-07-158013-1. 
• Chapelle, Howard I. (1951). American Small Sailing Craft. W. W. Norton & Co.. ISBN 0-393-03143-8.