Sloop designs are the most common variety of sailboat, The term sloop originates from the Dutch word slope. This design utilizes a mainsail and foresail with one mast. Sloops usually bend only one headsail, though this distinction is not definitive. Unlike cutters, sloops usually have only one headsail, though some sloops such as the Friendship Sloop have more than one sail. Sloops are popular with sport sailors, yachtsmen and as racing craft. Cutters are very similar to a sloop with a single mast and a mainsail. The cutter generally carries the mast further aft to allow for the use of two headsails attached towing forestays, the head stay and the inner stay carry the jib and staysail respectively. This is rarely considered a racing configuration; however, it gives much versatility to cruising boats, especially when there are high wind conditions.

Catboats today are used as a pleasure craft for day sailing. 19th century catboats were also used for racing. Ketch designs are sailing craft with two masts: a main mast, and a shorter mizzen. Both masts are rigged mainly fore-and-aft. Ketch boats are very popular among long distance cruisers. The additional sail allows for a better balance. Another popular sailboat configuration is the schooner. A schooner can have two or more masts. The second mast is at least as tall as the first mast. Sailboats are also classified by hull type. Most sailboats are built with a mono or a single hull. However, some boats are built as multi hull boats. These include catamaran and tri-maran vessels. When comparing a mono hull boat to multi-hull boat acceleration is much different. In a multi-hull boat acceleration to a top speed is very quick and almost instantaneous.

Sailing requires a high level of experience and skill. Crew must be able to quickly change rigs, rudder and dagger to change the speed and direction of the boat in a variety of sea conditions. In addition to steering the boat and managing the sails, crew must also have at least basic knowledge of some of the skills that are normally the responsibility of the captain. These can include weather forecasting, navigation, emergency repairs, marine electronics, first aid and others.