Anguilla is a British overseas territory. With a population of approximately 13,600 it's certainly one of the tinier trade mark jurisdictions in the world.
As a non-sovereign nation it is unable to sign up to International organisations and treaties; that remains the responsibility of the United Kingdom. Despite this, priority is available following amendments to local legislation and protection is accorded to famous marks.
The Registrar of Commercial Activities appears to be responsible for intellectual property on the island. They have a website dedicated to company incorporation; Anguilla being a popular tax haven. This allows for state-of-the-art electronic incorporation of Anguillian companies. Interestingly, this was developed in partnership with Companies House in the UK and the UK Government. This shows a willingness for Anguilla to cooperate although we can maybe conclude that the development of systems relating to IP may not have the same priority level.
Anguilla introduced design legislation in 2002 which provides for independent registration and, contrary to the UK IPO's page, UK registered designs no longer have effect. As for patents, UK and EP (UK) registrations can be extended although independent registration is now also available.
Trade mark registration does not take too long to obtain in Anguilla. In fact, it is particularly rapid if based on a UK registration; Anguilla having a dual system whereby applications can be purely local (substantive applications) or based on a UK registration. The 'based-on' option is also available for Community and International Trade Marks which is useful for global brand owners who prefer not to register in the UK individually.
With little prospect of Madrid Protocol accession, Anguilla should be praised for its efficient trade mark operations, which reflect international aspects as much as it can, to make it straightforward for foreigners yet, through it's substantive applications, remains accessible to locals from the region.