The Editor-at-Large of American Vogue would be the first to know that the Caribbean is very much back in fashion. Gone is much of the chintzy hotel décor of old, to be replaced by a new clutch of seriously slick hotels offering service to rival that in other luxury destinations, while those picture perfect beaches are as alluring as ever.
An Englishwoman in New York, Miss Wintour should - in the interests of patriotism - settle on an island with a distinctly British background, so we propose Anguilla, a British protectorate and pretty much our favourite island in the Caribbean.
The Viceroy Hotel
There, she should stay at the appropriately named Viceroy Hotel. She'll feel right at home surrounded by the thrillingly chic people that pass for the other guests. Her fashion eye can still be caught even on holiday; the hotel has its own extremely glamorous boutique curating the best of the collections and designer accessories.
Ms Wintour should know that Anguilla is a famously foodie island; the charming islet restaurant of Scilly Cay with its famous curried lobster and the Viceroy's very own Coba the best two places to eat. Get there before its in Vogue with your own bespoke package to the Caribbean this January.