The British Sail Training Association schooner Sir Winston Churchill is a 150.3 foot three-masted topsail schooner built in 1966 in Hessel, Yorkshire, England for the British STA to serve as a youth training vessel which could represent Britain in the Tall Ships Races. It's complement is 5 permanent crew, 11 volunteers or "afterguard" and 39 trainees or cadets (male or female) age 16-24. These cadets go on two week cruises nine months out of the year and are trained by the crew and afterguard. The Sir Winston Churchill caused quite a sensation when she showed up with an all girl crew of trainees in the 1972 Tall Ships Race.

The British STA raised about half the money required to build the schooner, named after Sir Winston Churchill who had died the previous year, when it signed the building contract. The rest of the money needed was raised through donations paid by public subscriptions. It was commissioned on March 3, 1966.

The schooner's rig was deliberately designed to incorporate all the main types of sail: square sails, gaff sails, staysails and a Bermudan mizzen. The masts are made of anodized aluminum to save weight aloft, but all the other spars are wood.

In 1967 a sister ship, the Malcolm Miller, was built. They are nearly identical. Externally they can only be told apart by their sail numbers, the shape of their deckhouse doors (arched on the Sir Winston Churchill, square on Malcolm Miller) and their figureheads. The 'Churchills' figurehead is a red English lion holding the STA's crest with a cross of St. George, the figurehead of the 'Miller' is a red Scottish lion holding the coat of arms of Sir James Miller, then Lord Mayor of London and former Provost of Edinburgh. The schooner was named in memory of his son Malcolm who had died in a car accident in 1966.

The schooners seldom sail together outside the Tall Ships Races: they tend to work their way around Britain on opposite coasts. They both take part in the European Tall Ships Races but only the 'Churchill' has taken part in a trans-Atlantic Race held in 1976 to celebrate the American Bicentennial.