The Virgin Group founder and Mr Obama spent time kitesurfing on Mosquito Island in the British Virgin Islands – an island which Sir Richard purchased for £10m in 2007.
Writing on Virgin’s website, the billionaire entrepreneur said it was an honour to invite Mr Obama and Michelle Obama to the island.
“So we decided to set up a friendly challenge: could Barack learn to kitesurf before I learned to foil board?” Sir Richard wrote. “We agreed to have a final day battle to see who could stay up the longest.”
Sir Richard posted a video of their challenge, with footage showing both men taking a dive in the water but the outgoing President coming out on top.
“Barack and I both fell many times, but we kept trying again and again and made progress over the days,” Sir Richard wrote.
“We were neck and neck until the last run on the last day, when I got up on the foil board and screamed along for over 50 metres, three feet above the water.
"I was feeling very pleased with myself, only to look over and see Barack go 100 metres on his kiteboard! I had to doff my cap to him and celebrate his victory.”
Since Mr Obama and his family boarded a Marine helicopter and left the White House after Mr Trump’s inauguration, they have enjoyed time off before returning to Washington so their 18-year-old daughter, Malia Obama, can finish school.
Sporting a backwards baseball cap and flip flops, Mr Obama could be seen pictured alongside Sir Richard.
While enjoying some R&R, Mr Obama found time to condemn President Trump’s hardline immigration order, which bans immigrants from seven Muslim-majority nations.
“The President fundamentally disagrees with the notion of discriminating against individuals because of their faith or religion,” Mr Obama's spokesman said in a statement.
“Citizens exercising their Constitutional rights to assemble, organise and have their voices heard by their elected officials is exactly what we expect to see when American values are at stake.”
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