This time however, when Branson lifts his anchor, he is hoping to break the sailing transatlantic record.
With "Virgin Money" written across his sleek sailing boat, which serves both for the voyage and advertising, Branson proves that as a business man, he is always on target, even off of land.
Early Show co-anchor Harry Smith had a chance to talk with Branson before he embarks on his journey.
"We hope it's the fastest sailing boat in the world. We want to try to break the record for the fastest crossing of the Atlantic, which is held in about six and a half days," Branson said.
Branson's sail boat can really pick up speed, which is essential for a sailor that holds about five world records.
"It will go up to about 45 knots. It goes fast. It has an incredibly deep keel which weighs many, many, many tons. And as long as nothing breaks and as long as we've got a nice big hurricane behind us pushing us, we have a shot at the record," he said.
Branson's successful track record speaks for itself.
"We were the first to cross the Atlantic, the fastest on the Pave, the first to cross the Atlantic in a balloon and the Pacific in a balloon," he said.
Records and adventures aside, Branson still has a genuine excitement of testing his own limits.
"I would much rather be participating in an adventure like this than sitting in front of a television watching somebody else do it. It's a technological achievement, and it's just a personal achievement, to see what one's capable of. And on this particular record, I'm actually bringing Holly and Sam, my children, as well," Branson added.
Branson's daughter happens to be a physician, so Branson has all of his bases covered as far as his health is concerned.
"I have my own doctor on board, and we've got a fantastically experienced crew. And hopefully we'll set off in a week or so," he said.
Although Branson wants to break a world record, he admits that everything he does in life has more than one reason for doing it, which includes promoting his new Virgin endeavors.
"It's a more fun way than taking out full-page ads in the newspaper. And Virgin America has been... we've been trying to sort of shake up the American industry with an airline and launch it in New York and Las Vegas and trying to offer a better quality of service. So indirectly, you know, you try to get a message across as well."
On the flip side, Branson also experiences a sense of nostalgia when it comes to setting sail near the one-year anniversary of when is friend and fellow sailor Steve Fossett went missing.
"We're very much doing this sailing race in his memory. He was the greatest adventurer in the history of adventurers. A great friend. I was lucky enough to go on one or two of his great sailing events, his big catamaran," Branson said. "Incredibly sad that he disappeared, but he's left a great legacy. And that's something that Americans should be proud of."