Sail plan in the context of Iceboat

A sailing ship is a sea-going vessel that uses sails mounted on masts to harness the power of wind and propel the vessel. There is a variety of sail plans that propel sailing ships, employing square-rigged or fore-and-aft sails. Some ships carry square sails on each mast—the brig and full-rigged ship, said to be "ship-rigged" when there are three or more masts. Others carry only fore-and-aft sails on each mast, for instance some schooners. Still others employ a combination of square and fore-and-aft sails, including the barque, barquentine, and brigantine.

Early sailing ships were used for river and coastal waters in ancient Egypt and the Mediterranean. The Austronesian peoples developed maritime technologies that included the fore-and-aft crab-claw sail and with catamaran and outrigger hull configurations, which enabled the Austronesian expansion into the islands of the Indo-Pacific. This expansion originated in Taiwan c. 3000 BC and propagated through Island Southeast Asia, reaching Near Oceania c. 1500 BC, Hawaii c. 900 AD, and New Zealand c. 1200 AD. The maritime trading network in the Indo-Pacific dates from at least 1500 BC. Later developments in Asia produced the junk and dhow—vessels that incorporated features unknown in Europe at the time.

Galleons were large, multi-decked sailing ships developed in Spain and Portugal. They were first used as armed cargo carriers by Europeans from the 16th to 18th centuries during the Age of Sail, and they were the principal vessels drafted for use as warships until the Anglo-Dutch Wars of the mid-17th century. Galleons generally carried three or more masts with a lateen fore-and-aft rig on the rear masts, were carvel built with a prominent squared off raised stern, and used square-rigged sail plans on their fore-mast and main-masts.

Such ships played a major role in commerce in the sixteenth and seventeenth centuries and were often drafted into use as auxiliary naval war vessels—indeed, they were the mainstay of contending fleets through most of the 150 years of the Age of Exploration—before the Anglo-Dutch wars made purpose-built warships dominant at sea during the remainder of the Age of Sail.

A barque, barc, or bark is a type of sailing vessel with three or more masts of which the fore mast, mainmast, and any additional masts are rigged square, and only the aftmost mast (mizzen in three-masted barques) is rigged fore and aft. Sometimes, the mizzen is only partly fore-and-aft rigged, bearing a square-rigged sail above.

In "Jackspeak" (Royal Navy slang), it also refers to the dress uniform of Junior Ratings.

A full-rigged ship or fully rigged ship is a sailing vessel with a sail plan of three or more masts, all of them square-rigged. Such a vessel is said to have a ship rig or be ship-rigged, with each mast stepped in three segments: lower, top, and topgallant.

The J Class of racing yachts were built to the specifications of Nathanael Herreshoff's Universal Rule. The J Class is considered the apex of the era when the Universal Rule determined eligibility in the America's Cup.

With boats costing $10-20 million to build and yearly upkeep around $3 million, J Class racing has been described as the "most expensive hobby on Earth".

A sailing vessel's rig is its arrangement of masts, sails and rigging. Examples include a schooner rig, cutter rig, junk rig, etc. A rig may be broadly categorized as "fore-and-aft", "square", or a combination of both. Within the fore-and-aft category there is a variety of triangular and quadrilateral sail shapes. Spars or battens may be used to help shape a given kind of sail. Each rig may be described with a sail plan—formally, a drawing of a vessel, viewed from the side.

Modern examples of single-person sailing craft, such as windsurfers, iceboats, and land-sailing craft, typically have uncomplicated rigs with a single sail on a mast with a boom.

A cutter is any of various types of watercraft. The term can refer to the rig (sail plan) of a sailing vessel (but with regional differences in definition), to a governmental enforcement agency vessel (such as a coast guard or border force cutter), to a type of ship's boat which can be used under sail or oars, or, historically, to a type of fast-sailing vessel introduced in the 18th century, some of which were used as small warships.

As a sailing rig, a cutter is a single-masted boat, with two or more headsails. On the eastern side of the Atlantic, the two headsails on a single mast is the fullest extent of the modern definition. In U.S. waters, a greater level of complexity applies, with the placement of the mast and the rigging details of the bowsprit taken into account – so a boat with two headsails may be classed as a sloop.