The former president reportedly spent two days learning the basics of how to fly a kite on dry land before he was finally allowed to graduate to the water.
After handing over the Presidential reins to Donald Trump, Obama, 55, and his family flew to Palm Springs for a long weekend before heading to the British Virgin Islands.
Speaking on his blog about holidaying with the Obamas, Richard Branson wrote: "It was a huge honour to be able to invite President Barack and Michelle Obama down to the British Virgin Islands for a complete break after Barack finished his second term as President and the family left the White House.
"So it was tremendous to offer him the chance to learn to kitesurf.
"The sport has really taken off in the past decade and we have the perfect conditions and team to help anyone learn.
"I have also wanted to learn foilboard surfing. So we decided to set up a friendly challenge: could Barack learn to kitesurf before I learned to foilboard?
"We agreed to have a final day battle to see who could stay up the longest."
Turns out, Obama was victorious in the challenge, despite falling off his board a fair few times in the lead up to the race.
Branson added: "After all he has done for the world, I couldn’t begrudge him his well-deserved win."