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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 oystering, but later appeared in other areas.
New Haven sharpies
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. Typically, in the summer, two masts would be stepped: one at the bow and amidships. In the winter, when heavier weather was expected, a single mast would be stepped in between. Larger versions, up to 35 feet, were crewed by two men. The New Haven models were typified by plumb bows with the heel of the stem sitting just out of the water, and rounded counter-sterns.
Although most sharpies were rigged as a cat-ketch with free standing, sprit rigs, 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 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.
A special place in history is for the former 1956 Olympic Class: 12m2 Sharpie.
- Boat building
- Catboat - a wider, gaff-rigged variation of the design concept
- Center for Wooden Boats - offers free rides in two classic sharpies, an Egret, and a New Haven type.
- Skiff - the general boat type upon which the Sharpie is based
- 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 knots 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 cruising 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 Boat Designs for Jim Michalak's homepage
- Parker Marine Enterpises for Reuel Parker's homepage
- NIS Boats main agents for Bruce Kirby's Norwalk Island Sharpies
-  Microcruising in the Bahamas - several small cruising sharpies designed by Matt Layden - photos, sketches, hints
-  Paradox a Matt Layden micro-sailboat coastal cruiser - construction photos, owners' photos
-  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.
- British Sharpies in Rio de Janeiro, Brazil Sailing out of the Caicaras Country Club on the Logoa in Rio back in the 1940s through the 1970s; reportedly, the fleet moved across the Guanabara Bay to the City of Niteroi.