The opening Test will begin on Tuesday in Antigua, with plenty to ponder for the tourists.
Here, Planet Sport takes a look at the five key talking points ahead of the first day in the Caribbean.
1 - All eyes on Root's leadership
Joe Root's captaincy came under questioning as England returned from Australia having suffered an embarrassing 4-0 defeat in the Ashes. Head coach Chris Silverwood, assistant Graham Thorpe and director of cricket Ashley Giles all lost their jobs, while Root was offered the chance to lead the revival.
Having led the side 61 times, he is already England's most experienced skipper, but he must now prove he has the desire, drive and nous to lead the rebuild. His move to number three in the order shows he is not shirking the challenge.
2 - Was omitting Anderson and Broad the right call?
The decision to axe James Anderson and Stuart Broad from the England squad drew a reaction not seen since the departure of Kevin Pietersen.
Neither man could've been accused of underperforming in Australia, but at 39 and 35 respectively, the decision was made to leave them at home. With Ollie Robinson now injured, the seam attack has already lost one key pillar, leaving much on the shoulders of all-rounder Chris Woakes and speed specialist Mark Wood.
Craig Overton, who was an unused squad member throughout the Ashes series, is also set to take a heavy load. With two interested observers taking notes several thousand miles away, it is a gamble that needs to go well.
3 - Can Lees solve England's opening problems?
Rory Burns and Haseeb Hameed both endured a disastrous Ashes series Down Under, paying with their places in a revamped squad.
Opening the batting has been a precarious position for England since the heady days of Sir Alastair Cook and Sir Andrew Strauss. In fact, county cricket's brightest and best have queued up to try their luck, however none has to yet to make a lasting impression.
One man hoping to change that is Alex Lees. The Durham batsman deals in consistency and has a more orthodox technique than some who have come before. England's selectors will hope that those two qualities will allow to transition smoothly. On Tuesday, he will become the country's 701st men's Test cricketer.
4 - The time has come for Ben Foakes
It's fair to say that Ben Foakes has had his patience tested in recent years. The Surrey wicketkeeper routinely wins plaudits as one of the game's most accomplished glovemen, yet he regularly failed to catch the eye of the England selectors.
Just eight Tests in three-and-a-half years isn't exactly a large body of work, particularly after Foakes scored a century on debut in Galle and was later named player of the series.
Nevertheless, now that he has the confidence of knowing he has been backed as number one, he will be looking to prove just why he is regarded as a world-class operator.
5 - Never easy in the Caribbean
Whenever England are in town - no matter what form they're in - the West Indies turn up. Whether that's something to do with the big travelling crowds, well-founded historic grievances or the desire to upset a member of the modern 'big three' does not entirely matter.
What does matter though, is that things tend to get tough for the English on these islands. In fact, they have triumphed in a Test series just once since 1968 - with the class of 2004 holding the honour - and were on the end of a 2-1 upset last time out.
When it comes to Antigua, things are even worse considering England have never won a single Test here in 10 attempts.