The Contessa 26 is a 7.77 meter (25.6 ft) fiberglass monohull sailboat, brought about when Jeremy Rogers, with a background in traditional wooden boatbuilding along with one of his Folkboat customers, David Sadler, created a modified version of the same boat in glass reinforced plastic (GRP).

[1] Rigged as a masthead sloop, with a long keel and a hull-mounted rudder, the Contessa 26 was launched in 1966 and early boats proved to be very successful racers, including long-distance events.

The Rogers boat works built approximately 350 Contessa 26s from 1966 to 1977, after which the moulds were sold to Chris Carrington of Maclan Marine, Lymington, who produced a few more during 1977/8.

[7] 1974 Round Britain Richard Clifford with David Barrie as crew sailed Shamaal ll to 24th Overall, 4th on Handicap, out of 61 starters and 39 finishers, after 25 days and 20 hours of racing.

[8] 1976 Observer Single-handed Trans-Atlantic Race (OSTAR) David Sutcliffe sailed Lady Anne of St Donats to a 61st place Overall, 43rd in the Jester Class (yachts under 38 feet LOA) in a time of 44 days and 3 hours.

Evidence of this boat's abilities as a bluewater cruiser can be found in the fact that it was chosen by both Tania Aebi and Brian Caldwell in their separate attempts to set the record as the youngest person to complete a single-handed circumnavigation.

[16] Canadian Stéphane Tremblay, sailed singlehanded and engineless from Sandy Hook, New Jersey to Spain via the Azores and back against the trade wind, aboard his J.J. Taylor Contessa 26 Joshua III on 15 May 2008.