Dylan Farrell ’11: Education Happens Everywhere

Whenever you’ve been asked, “What did you do this summer?” it’s unlikely that your response comes close to what Dylan Farrell ’11 would say about his summer of 2023.

Dylan’s adventure started in March. Well, really, it started 22 years ago, in 2001 when his grandfather, Roger Peel, sailed his 45-foot Island Packet 420, named Island Magic, from Florida to Barbados, where he would live for the next 20 years. When the time came for Roger to move back to the Northeast, a decision had to be made about the boat. Who would take it and how would they get it up north? Dylan decided to step up. 

“I've been sailing most of my life, so I told him, ‘I'd be interested in keeping the boat in the family and sailing it up from Barbados to Connecticut.’ I've been planning the trip for the past year,” Dylan told The Foote School from a marina in Norfolk, VA, this August.

A competitive sailor since age 5, Dylan went to Choate Rosemary Hall after he left Foote in 8th grade. At Choate he captained the sailing team, leading them to victory in the Connecticut State Fleet Racing Championships in 2014. Dylan then moved on to Harvard, where, while earning a joint degree in math and statistics, he also captained its sailing team. Yet he knew that a strong background in competitive racing didn’t necessarily mean that he could safely helm the much larger, much heavier Island Magic through the Caribbean Sea and up the east coast of the U.S. Plus, Dylan had a full-time job as a machine learning engineer. In San Francisco.

His company let him transition to part-time so he would have this opportunity, and Dylan enrolled in a number of safety and certification classes, prepping for off-shore passages and celestial navigation. He also spent a week sailing around the Caribbean to gain experience.

“That was really helpful in giving me some actual experience in doing those types of passages in the area where I was going to be sailing,” he said. “And then having the certifications was a nice bonus as well.”

There were boat repairs to be made, and hundreds of tiny logistics that had to be lined up, but ultimately Dylan realized he needed to follow the wise words of one of his instructors: “Just leave the dock.” He left the dock in March — waiting until after the dreaded “Christmas winds,” an emboldened and often dangerous version of the Caribbean’s consistent trade winds. He also needed to leave early enough to hopefully avoid hurricane season.

Dylan was joined during the journey by his friends and family — including his mother and all of his siblings (Garret ’09, Caitlin ’12, and Tagan ’17) — picking up different people at different stops along the way. At one point, he even offered to transport a stranger from one island to another. The stranger not only recognized the boat, but had sailed with Dylan’s grandparents 19 years before. The ability to strengthen these connections with his family, his friends, and the outside community is part of what attracted Dylan to the trip in the first place.

There were trials, of course. Yet Dylan’s experience allowed him to captain his crew safely, turning 8-foot waves near Turks and Caicos into an enjoyable ride — and an opportunity to move a little faster. It also became a standout moment in his journey. To hear him reflect on his sail across the banks in the Bahamas, atop just 15 feet of clear, blue water, but with no land in sight for miles, makes even the most land-locked-lubber ache for a chance to glide across the sapphire sea for a moment.

“It's been a great experience being out on the open ocean for many miles, doing something that very few people do nowadays. Just that feeling of experiencing nature — both the beauty of it and then all the challenges with weather — having that kind of learning experience has been really cool,” he beamed.

He has also enjoyed the time to bond with his grandfather over this shared experience, though his grandfather had done the journey in the other direction. The two kept in close contact throughout the trip.

“I think there were some of the things he was talking to me about going into the trip that I didn't fully appreciate until doing them myself,” he acknowledged. “He has been very excited about this, and he is definitely happy that the boat will stay in the family, and that we will be able to have great experiences sailing on her for years to come.”

Dylan plans to dock in Connecticut in late August, after stopping in New Jersey to compete in the International Lightning Class Association North American Championship. Then he’ll return to San Francisco, but that’s not the end of his adventures.

Alongside his father Stephen (retired Dean of Faculty/English Teacher at Choate) and sister Caitlin, Dylan is opening an online international high school, called High Aspirations. Founded on the principle of “Elite Education for Everyone,” the school believes that “education is the best tool for unlocking human potential. We are building an online community that connects highly motivated students all over the world with elite teachers to help them turn their dreams into realities,” according to its website. 

“We want to provide some of the elements that we know and love from our own education — going to schools like Foote and Choate — and bring those to areas of the world that don’t have access to it,” he explained.

The school is in its beginning stages, and the Farrells are building up their course offerings and faculty, but they hope to be fully underway by next year. To learn more, visit highaspirationsschool.com.

“I definitely feel inspired to do some more adventurous things in the future, with that mentality of — you just need to ‘get off the dock’ instead of waiting for everything to be perfect,” Dylan said.