Over 12 gruelling days, the former Mariners' winger will cycling from the most south-westerly point of England, along the Welsh border, the Lake District and the Highlands to reach John O’Groats in the Scottish Highlands.
Day one consists of a total of 70.45 miles with 4,803 feet of climbing, taking him from Land's End to Liskeard.
All the money raised from the bike ride will go towards supporting the club's youth system.
You can make donations at any time by clicking here
Follow his daily progress on our official Twitter.