Cayman’s Guy Manning, Chris Smith, Jon Roney and Andy Childe will cycle nearly 900 miles over seven days from Land’s End at the southern tip of England to John o’ Groats in Scotland this month.

The latest challenge of Guy Manning’s life begins at Land’s End.

Mr. Manning, who has already scaled Mount Everest and been part of a relay team cycling across the United States, will bike the length of the United Kingdom with a group of friends later this month.

Three of his six peers – Chris Smith, Jon Roney and Andy Childe – hail from the U.K. but live in Cayman, and they have been preparing for the trip by cycling around the East End loop for the last few months.

“We’ve all been doing the training,” Mr. Smith said. “We’re all very stubborn as well.”

Their journey – from Land’s End at the southern tip of England to John o’ Groats in the northern end of Scotland – will take seven days and nearly 900 miles up and down hilly terrain. The group will pull into their final destination on July 29, the same day as the climax of the Tour de France.

The group’s race up the western edge of Great Britain will be self-funded, and they will raise money for the Cayman Islands Cancer Society and the St. Baldrick’s Foundation. Most of the group has never done a journey like this, and they will be leaning on Mr. Manning, who has scaled the tallest peaks on all seven continents.

“It’s a good bunch of friends looking forward to the challenge,” Mr. Manning said. “I’m excited about it. The goal really is to raise as much money as we can. That’s the objective, and if it tempts people to get out on their bikes, that’s a great thing too. But it’s really about the charity and fundraising.”

Mr. Smith said the group has been preparing by cycling about 100 miles a day on weekends here in Cayman, but new tests will be the elevation of the terrain and England’s fickle weather. The journey will require the group to traverse about 125 miles a day for seven straight days, piling on the difficulty over a week.

“I think it’s important that we stick together as a group. We can take it easy,” said Mr. Smith of the 875-mile journey of a lifetime. “Guy Manning has done a lot of things. The rest of us, we’ve done a few Ironman races. We have marathons and all those kind of things under our belt.”

Mr. Manning compared this journey to his Race Across America, in which he and three pals took turns cycling nearly 3,100 miles nonstop across the United States. That ride took him over the Rockies and the Appalachian mountain chains, priming him for a jaunt around the perimeter of his homeland.

But is one race harder than the other? Mr. Manning said they both present their own challenges.

“It sounds, on paper, a lot easier, but we all ride the whole race, whereas in America, we all rotated,” he said. “It’s actually a pretty similar distance ridden each day. But the advantage here is we get to sleep in a bed each night. In Race Across America, there was basically no sleep. We were constantly in the van bouncing along the road …. I’m hoping to get a bit more rest this time.”

The group’s tired legs will begin to weigh heavier and heavier as the trip progresses, and Mr. Manning said the toughest day could come on the fourth day. That day will take him near the town his parents live in – Hutton Roof – and will bring the group over the border separating England from Scotland.

“We’re riding from Wigan to a place called Gretna Green,” he said. “That’s about 125 miles, but it will take us right through the English Lake District, which is the most mountainous part of the U.K. There will be a lot of climbing that day. But that’s where I grew up, so I’m looking forward to that day.”

Mr. Manning said his family might actually be reassured that he’s only cycling hundreds of miles and not trudging his way up a mountain.

“They’re pretty used to me coming up with things,” he said. “I think Mom and Dad are happy we’re riding the U.K. instead of telling them I’m climbing Everest or something of that sort. It’s a bit safer. This is a nice challenge, and next year I’ll be looking to do something more exotic again out in the wilderness.”

People who want to contribute to their cause can visit the group’s GoFundMe page www.GoFundMe.com/chnjrf-bike-for-cancer.

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