With a cheeky grin, Dean Bragonier nimbly hopped down the rocks on the Sengekontacket Pond side of State Beach in the morning sunlight. He couldn’t wait to get into the water.

Starting July 11, the 42-year-old resident of Vineyard Haven and Cambridge will hardly have time to get out of the water as he embarks on a 27-leg swim around Martha’s Vineyard. Mr. Bragonier, who recently founded NoticeAbility, a nonprofit that creates dyslexic-friendly learning tools for middle school-aged children, will be completing the 50-mile swim to raise awareness about the learning disorder he’s grappled with since his youth. Dyslexia affects the ability to read, despite normal intelligence.

Mr. Bragonier said the swim is a metaphor for the struggles experienced by people with dyslexia.

“We have a very daunting task and it’s very substantial in nature, but we are exceptional creative problem solvers,” Mr. Bragonier said. “That is exactly what I’m going to be experiencing in the next 38 days: changing tides, currents, weather, summer traffic, boat traffic and big marine life that wants to gobble me up, and how I will persevere is through persistence, creative problem solving and reaching out to those who can help me.”

He has received help from both Islanders and friends from off Island. To physically prepare for his dunk, Mr. Bragonier began training in January and employed what he called a trifecta: a long-term training schedule from the head swim coach of his alma mater, Bates College, Peter Casaras; the smart phone application Lift Sessions (developed by an old high school friend); and grueling training sessions with the Cambridge Masters Swim Club. For the actual event, a wealth of local involvement has ramped up his excitement.

“On last count, three police chiefs want to do a leg with me,” Mr. Bragonier grinned. “I always encourage big, built guys with massive handguns to join me on any swim.” County sheriff Michael McCormack will also assist by trailing Mr. Bragonier in a boat as he swims.

This sort of camaraderie is exactly what Mr. Bragonier wanted the event to engender. “Being able to swim with people that care and want to see our collective success as a population is so fulfilling,” he said. “We do this fascinating physical endeavour in a hostile environment and you emerge with a level of camaraderie that you can’t get sitting around a coffee table or in an office space.”

While training in the open water, Mr. Bragonier said he got to see a part of the Island where not everyone thinks to look. “There’s so much cool life out there,” he said. “I was swimming at Lambert’s Cove last week, and these massive striped bass kept coming up and just peeling out underneath me and all these rock crabs and spider crabs perpetuating their species and feeling very encumbered by my surprising presence. There’s like this whole life under these waters.”

But he is not excited about all the wildlife he may encounter in the waves. After talking with Greg Skomal, a senior biologist with the state Division of Marine Fisheries and a shark expert, Mr. Bragonier admits to feeling fear. “I am most worried about the south shore,” he said. “Basically what I’ve determined is I’ve got to swim in the break; according to Greg’s calculation that’s the best way to ensure my safety. The south shore has got some really gnarly surf — at one point I’ve got a three-mile leg out there and that’s a serious physical exertion. The 40th anniversary of Jaws this summer and having that theme track in my mind doesn’t help either. That’s what’s keeping me up at night: the south shore.”

Despite nightmares about sharks, Mr. Bragonier is confident about his ability to complete the swim.

With the help of Charlie Morano, a recent Martha’s Vineyard Regional High School graduate and aspiring documentarian, Mr. Bragonier is documenting his swim with one short video blog per leg, in which he hopes to bring out voices from the dyslexic community.

“It’s to create an accessible narrative to families and to kids who are dealing with the negative ramifications of dyslexia,” he said. “To provide a real life example and the voices of people from all walks of life who have come to recognize dyslexia as the ingredient to their success as opposed to the albatross around their neck.”

Mr. Bragonier, who grew up coming to the Island and once owned an Oak Bluffs restaurant, said he chose the Island to swim around because of the community, the beauty and the diverse summer population. “It’s an accelerator that really is offered in very few places in the world,” he said.

The swim will begin July 11 from the small bridge at State Beach, and move counter clockwise around the Island in legs of two to three miles. The schedule is three days of swimming, one day of rest. The final leg, a community swim with incremental starting points, will be on August 16.

Mr. Bragonier's video blogs about his swim are available on YouTube.