But Pearson has experience in beating the odds.
At 18, a doctor told him he would be paralyzed from the waist down by the time he turned 35 as a result of polio he contracted in his right leg as an infant in the African nation of Kenya.
After a series of reconstructive surgeries, including bone and muscle transplants, bone removal, and leg straightening, Pearson learned to walk unaided at the age of 11. He eventually played in his high school's first soccer and volleyball teams and as a reserve in basketball and cricket.
At age 40, five years after he was supposed to be paralyzed, Pearson bicycled 530 miles in eight days through the foothills of the Drakensburg Mountains in Africa in November 1994 to raise money and publicity for the Meals on Wheels program.
He finished the last 370 miles of that trip with the cartilage in his left knee torn in two places.
Though he's no stranger to pain, Pearson expects his trip across the Atlantic will not only test him physically, but mentally.
"You have to switch it off. You have to focus so much on what you're doing. You can't dream about anything. You just have to look at the wave in front of you which, after 10 minutes, becomes very boring," he said.
With Pearson will be a team of about 15 Highland View Academy students and a crew aboard a 110-foot yacht and two, 24-foot inflatable boats to provide support.
"When I first heard about it, I thought it was crazy," said Melissa Bowen, 16, of Hagerstown.
But Bowen and her brother, Stephen, 18, are both accompanying Pearson on the unprecedented trip.
Each student will be assigned to and receive instruction in a specific job and all of them will undergo intense physical training with Pearson months before the trip.
"I'm excited. I'm kind of anxious to do this. It'll be a good experience physically, mentally and spiritually," said Aaron Miller, 16, of Hagerstown.
Miller will be a so-called handler on the trip, helping with refueling Pearson's Jet Ski twice a day at sea, assisting in docking and landing, and hoisting Pearson from the craft to the yacht where he'll sleep after riding for 16 hours straight in the water.
"You definitely can't have a reckless attitude towards the sea. You need to respect it - know its moods. You have to know when your body has had enough and when to call it quits for the day," said Pearson, who comes from a long line of seamen.
Three years in the planning, Pearson and his students worked out a route, factoring in water and air temperatures of the ocean, the roughness of the sea, and shark populations.
The group plans to fly to Scotland where they'll embark from Glasgow, travel down to the British Isles, past France, Spain and Portugal, to the Azores, across to Bermuda, and up the East Coast, ending in Baltimore.
Pearson hopes to raise enough money through sponsorships to pay for the trip and to help Highland View Academy build a new gymnasium, tennis courts and a dormitory.
He also plans to donate some of the proceeds to the American Neurological Disorders Council.