Looking Back: 10+ Years of Youth Sailing with Coach Pat DiLalla
As we patiently await the return of summer, the change of season brings a new chapter here at the ‘Shop. After more than a decade, our long-time High School Sailing Coach, Pat DiLalla, is setting off for Maine Maritime Academy to lead their varsity sailing program. We recently sat down with Pat, reflected on his time with us, and celebrated some important milestones through the years.
Pat grew up outside of Cleveland, visiting family in Maine over the summers of his youth. His mom signed him up for sailing lessons at a club near South Bristol—which he reluctantly attended. Though he’d had a keen interest in the water and gravitated towards books like Treasure Island and Carry on Mr. Bowditch, he approached sailing with great trepidation. The “what if” factor was ever-present in the back of his mind. “What if I accidentally jibe? What if I capsize? What if I can’t right my boat?”
He recalls a pivotal breakthrough at age 14, when he and an instructor were sailing one of the club's dinghies. A mighty breeze picked up and had the boat healing hard over and panic began to set in. The instructor noticed and reminded him “it’s only water” as she methodically eased the main sheet and allowed the boat to right itself. “In that moment I was astonished at how calm she was. Kids pick up on things more than adults often realize, and seeing her keep her cool is something that’s stuck with me through all my years of coaching.”
In 2003, Pat joined the ‘Shop as Head Instructor during an early iteration of our community sailing program, beginning his own journey as a coach. Two years later, he acquired Plumbelly - a 26’ wooden sloop—from a former Apprentice. Drawing inspiration from the youth he’d worked with, he set off on his own big adventure: sailing the vessel to the Caribbean, Azores, Morocco and beyond. Some voyages with a friend in tow, but many by himself—including the final Atlantic crossing which brought Pat and Plumbelly back to Rockland Harbor in 2009.
Upon arriving, he hailed KC Heyneger (Waterfront Director at the time) and casually announced his homecoming. That fall marked the official start of the High School Sailing program, with Pat taking the helm. His unique experiences - both as a reluctant young sailor and having many opportunities to “learn by doing” while voyaging informed his coaching style. Over the years, more than 300 local youth have participated under his leadership - many of whom were brand new to sailing, just as he was years before.
“Seeing these kids show up, willing to try something completely foreign — willing to step outside of their comfort zones — is truly remarkable. It’s inspiring to be a part of.”
He remarked on the transformative nature of the program, and how it truly allows its participants to discover their power. “I’ve watched kids go from being terrified to set foot on a boat to navigating incredibly challenging conditions with grace and ease—situations that would make most adults panic.” Racing often means close-quarters sailing that requires quick thinking, and countless times the students showed their skills with poise. He shared a fond memory of a student who entered the program with no experience. She’d spent a few seasons crewing and learning sail handling; during her Junior year she challenged herself to take the helm. In the spring of her senior year at the Down East Championships, she skippered a 420 in the B Division - and won a first place in an extremely competitive fleet of 20 boats. "The look on her face when she landed on the dock was absolutely priceless"
The impact of these experiences reaches beyond the waterfront. He recalls one timid student who went on to attend Maine Maritime Academy and become a leader in the Regiment; another who sailed from 7th - 12th grade is pursuing a career as an aircraft pilot.
"It's been a privilege to work with so many wonderful students over the years; they have shaped who I am as much as I have them, and they've taught me that everyone has the capacity for greatness in some way."
Pat’s legacy of leadership has paved a bright path for generations of young sailors to come, and we’re truly grateful for his dedication over the years—a pivotal piece of Apprenticeshop history.