Until 1967, the only flag flown in Anguilla was the Union Jack of Great Britain. The 1967 revolution prompted the introduction of another flag, featuring two mermaids with a shell between them. This flag was sent by a group of Anguillians living in San Francisco and was hoisted when the Statehood flag was torn down. It was never really accepted and was soon replaced by the Three Dolphins flag, which immediately became popular and is still used by many People today, although unofficially. The three dolphins are coloured orange, to represent endurance unity and strength, and are in a circle for continuity. The flag has a white background, for peace and tranquility, with a turquoise-blue base representing the surrounding sea and also faith, youth and hope.

The 'Union Jack and the Three Dolphins flags were used for many years but there was a strong feeling that Anguilla should have its own official flag. A previous Governor of Anguilla, Mr. Brian Canty, suggested a new flag and drew sketches which were sent to London for approval by Her Majesty the Queen. The new flag, which was first hoisted on 30 May 1990, is a blue ensign with a Union Jack in the top left corner and a shield on the right side which shows three orange dolphins on a white background with a turquoise-blue base. The design thus incorporates affiliation to Britain and the Anguilla Three Dolphins flag.

The governor's official flag comprises the Union Jack and the Anguilla coat of arms surrounded by a laurel wreath. It is flown at Government House when the Governor is in residence and on any motor car or boat in which he is making an official visit. The coat of arms uses the same dolphin design that appears on the flag and is edged with gold. The official seal is the shield with a double circle around it containing the words Anguilla: Strength and Endurance.