England have been back to the Caribbean twice since 2004 - but with little success on either occasion.
A poor performance at the 2007 World Cup hastened the departure of coach Duncan Fletcher, while the $20m winner-takes-all Twenty20 game in Antigua in 2008 - bankrolled by Sir Allen Stanford - finished in a humilating 10-wicket defeat.
BBC Sport report: Dismal England knocked out of Cup
BBC Sport report: England thrashed in $20m showdown
Since returning from India in December, both coach Peter Moores and captain Kevin Pietersen have departed - leaving Andrew Strauss as the new skipper.
Although both are left-handed openers, Strauss and new West Indies captain Chris Gayle are contrasting cricketers.
Strauss, the "safe pair of hands", is often dubbed "posh" by his team-mates, and these days is more of a careful accumulator of runs than a thrilling risk-taker.
Gayle, from Jamaica, is one of the most explosive hitters in the game - but is often described as a "laid back" character, even by his own official website.
But who will prevail this time?
Gallery compiled by Mark Mitchener
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