The Bermuda sloop is a type of fore-and-aft rigged sailing vessel developed on the islands of Bermuda in the 17th century. In its purest form, it is single-masted, though some ships with such rigging can be built with as many as three masts, which are also known as Schooners. Its original form had gaff rigging, but evolved to use what is now known as Bermuda rig, which had been used on smaller Bermudian boats since the early 17th century, making it the basis of nearly all modern sailing yachts. Although the Bermuda sloop is often described as a development of the narrower-beamed Jamaica sloop, which dates from the 1670s, the high, raked masts and triangular sails of the Bermuda rig are rooted in a tradition of Bermudian boat design dating from the earliest decades of the 17th century.
The development of the rig is thought to have begun with fore-and-aft rigged boats built by a Dutch-born man who relocated to Bermuda in the 17th century. Captain John Smith reported that Captain Nathaniel Butler, who was the governor of Bermuda from 1619 to 1622, employed a Dutch shipbuilder, Jacob Jacobson, from the crew of a Dutch frigate which had been wrecked on Bermuda. Due to the success of the sloop, the shipbuilder quickly established a leading position among Bermuda's boat makers. In fact, King Charles II, seen in a painting arriving aboard a vessel in Rotterdam in 1660, was so enamored with the ship that his successor, The Prince of Orange, would later gift him one, which Charles named Bezaan.
Initially influenced by the Mediterranean lateen rigs introduced during Spain's rule of their country, the Dutch had modified the design by omitting the masts, with the yards of the lateens being stepped in thwarts. By this process, the yards became raked masts. Lateen sails mounted this way were known as leg-of-mutton sails. The Dutch called a vessel rigged in this manner a bezaanjacht (). The Bermuda sloop differed from other sloops partly in the form of its hull, which was very stiff. This stiffness was a result partially of the shipbuilding skills on the islanders, but also thanks to the availability of large quantities of Bermuda cedar, which has superior qualities of rot-resistance, low density (making the ships lighter and faster) and high strength (making the ships more durable). The vessels carried little fixed ballast, which allowed them to transport large cargoes. Designed to sail primarily on the open ocean, their relatively deep hulls gave them superior seaworthiness by comparison to similar vessels, such as the Baltimore Clipper, which were intended to operate in coastal waters. The fore-and-aft rig was particularly useful in maneuvering upwind. Moreover, single-masted Bermudian sloops were optimized for speed. This made them a very demanding craft to sail. In rough weather, they were easily swamped.