The business tycoon, 66, confessed that despite experiencing treacherous weather conditions on some of the days, completing the first half was very rewarding.
"Everyone is getting stronger and stronger," he said. "There are some people literally licking their wounds. As long as we don't have a repeat of that hopefully we'll be ready for the gruesome ending."
Watch the video below to find out exactly how the team are feeling:
Virgin STRIVE Challenge is raising money to support Big Change, a charity founded by Sam Branson, Holly Branson and Princess Beatrice among others, to support youth projects in the UK which help young people thrive in life.
Reaching the end of the first half, Richard said: "This particular leg ended on such a high note, going through beautiful mountains and the sun was out.
"It was quite as long as usual and as you can see everybody is on a real high. And I'm strong, I'm really looking forward to a rest day tomorrow but more importantly I'm looking forward to moving down to the south of Italy."
Sir Richard Branson has revealed his joy at reaching the half-way mark of the 2000km Strive challenge
The gruelling sees Richard, Holly and Sam, along with hundreds of sports enthusiasts cycle to the southern tip of Italy, swim to Sicily, mountain bike to the foothills of Mount Etna before finishing with a run to the summit of the infamous volcano.
"We have done ten days of cycling now," said Holly. "The first five days were super tough, it was mentally challenging as I've never done that length of cycling before.
"It was utterly monotonous, I was like 'I can't do this 15 days straight'. But your body and mind gets used to it. Today the sun is out which is an added luxury, everybody is really happy. Yesterday was a miserable day, it rained nonstop, and there was thunder and lightning. There were moments where I was cold to the bone."
Virgin STRIVE Challenge is raising money to support Big Change
This year's challenge is double the distance of the last challenge undertaken in 2014, which raised over £750,000 for Big Change.
They have raised just under £800,000 so far for Big Change which supports UK youth projects.