The Cutty Sark was built in 1869 as a merchant vessel, and was later used as a training ship and finally put on public display. Its name translates from Scottish and means "little shirt". The phrase "Cutty Sark" was popularised by Robert Burns in his poem Tam o'Shanter, as the nickname of the character Nannie.

The ship was badly damaged in a fire in 2007, and is undergoing extensive renovation work.

Clipper ships were very fast sailing ships popular in the 19th century. They were named clippers due to the now-archaic 17th century meaning of the word clip, meaning to go at speed; the clippers were built for seasonal trades such as tea, where an early cargo was more valuable than massive loads. They were designed for low-volume, high-profit goods, such as spices, tea, passengers, and mail.

The Cutty Sark was designed by Hercules Linton and built in 1869 at Dumbarton, Scotland. Its captain was John (or Jock) "White Hat" Willis. At the time of the ship's inception, the tea route from China to London was a highly-competitive sprint. Great profits could be had for whichever ship made it into dock with the first tea of the year.

As sailing entered the steam era, the clipper ships eventually lost out. Steam ships could deliver cargo more reliably, if slightly less quickly, and in the end, this proved better business. In the late 19th century, the Cutty Sark diversified into the Australian wool trade, ferrying wool from Australia-to-Britain in as little as 67 days. Her best run was 360 nautical miles (414 normal miles) in 24 hours, an average of 17 normal miles an hour. At the time, it was said to have been the fastest run of any ship of her size.

From 1895 to 1954 the Cutty Sark changed hands (and roles) numerous times. She was first sold to the Portuguese firm Ferreira, then dismasted off the Cape of Good Hope, re-rigged and resold and then restored to her original status and used as a training ship. Finally, in 1954 she was moved to a custom-built dry dock in Greenwich where she became a popular tourist attraction.

On 21 May 2007 the Cutty Sark caught fire and burned for several hours. However, damage was not so bad as had been feared as much of the original "fabric" of the ship (including original timbers etc) had been removed during a major preservation project that was underway at the time. In fact, less than 5% of the original fabric was lost in the fire.

Although there was suspicion that the fire had been started deliberately, the London Fire Brigade announced in 2008 that their investigation had concluded that the most likely cause was the failure of an industrial vacuum cleaner that had inadvertently been left switched on for 48 hours before the fire started.

Oscar-winning producer Jerry Bruckheimer aided in the restoration of the Cutty Sark by donating a collection of around thirty photographs taken on set during the filming of Pirates of the Caribbean: At World's End. The photographs were shown in the Cutty Sark exhibtion centre to raise funds for the damaged ship.