The Pearson 365 was built from 1976 until 1982 and became one of Pearson's most successful cruising boats along with the Pearson 424. The Pearson 365 was available in the form of a Ketch, Sloop, Cutter (Sea Dragon) and Pilot House.

In addition to a highly modified interior the Pilot House is equipped with addition fuel capacity and a larger engine is located mid-ship eliminating the need for V-drive. The mast on the Pilot House and the Sloop are the same, 2.5 feet taller than the Ketch and with a boom that is 1.25 foot longer than the Ketch. The cockpit is slightly smaller to accommodate the larger saloon.

All in all about 30 Pilothouse Pearson 365 were built between 1979 and 1981.