Nicholas Alley BrilliantAs master of Mystic Seaport’s schooner Brilliant, Captain Nicholas Alley leads a very successful sail training program aboard one the loveliest boats on the water.

“I grew up in Boston, Massachusetts,” says Nicholas, who lives in Mystic, Connecticut. “My father, Brian Alley, taught me how to sail when I was about nine years old. My first boat was a Dyer Dhow that was the tender to a boat that my father and I were rebuilding. He bought an old, 25-foot wooden Navy launch hull, and we converted it into a sailing vessel. It was a neat boat! When I was 11, I started sailing at Community Boating on the Charles River. The folks there taught me a lot…it’s just a great organization.”


“I went to Boston Technical High and Madison Park High in Boston. I was washing and maintaining boats at a sailing club in Boston, and got on a delivery going south and ended up teaching sailing for the Annapolis Sailing School in St. Croix, USVI. They sent me to Sea School, where I got my first license, and I worked winters in St. Croix and summers in Annapolis when I was in my early twenties. The first ship I sailed on was called Rambler. She was a biological education vessel out of Gloucester, doing whale watch studies throughout the Caribbean and the East Coast. That was a very early sail training program.”

“After that, I sailed with the Lady Maryland Foundation on the Chesapeake Bay. I sailed as chief mate on Lady Maryland and made the connection between wooden boats and working with kids, which continues to this day. I sailed as chief mate on Pride of Baltimore II, and as captain of a motor vessel called Mildred Belle. In 1992, I started sailing with the organization that became Ocean Classroom as third mate engineer aboard Spirit of Massachusetts. I’ve been captain of all three of Ocean Classroom’s vessels: Spirit of Massachusetts, Harvey Gamage, and Westward. I’ve also sailed as captain of Bill of Rights in a liveaboard program for at-risk youth called VisionQuest. I co-captained the Lettie G. Howard for a year, and was the first captain of schooner Virginia when she was built in 2005. I lived on the Chesapeake for about 30 years before moving back to New England to take the job on Brilliant, and this is my fourth season as captain.”

Brilliant is an amazing boat with a great pedigree, and I love sharing her with others,” Nicholas enthuses. “She was designed by Olin Stephens in 1931 and built in 1932 at the Nevins yard on City Island, and she crossed the Atlantic that year. She was built as a private yacht for world cruising, although she has a very good turn of speed. She served as a patrol craft in the Second World War, primarily for submarine spotting. Briggs Cunningham bought her after the war and had her rerigged to make her more competitive. In addition to a number of Bermuda Races, he used her as a platform for teaching and was taking kids out sailing on the western Sound in the late forties. Briggs envisioned that Brilliant would do what she continues to do to this day, and he donated her to Mystic Seaport in 1954 for sail training. She’s an iconic vessel – I regularly have people come up two or three times a week when we’re in port and say, ‘I sailed on her!’ It could be last year or it could be 50 years ago.”

Nicholas leads Mystic Seaport’s Teen Sailing Programs aboard Brilliant. “We have 5- and 10-day programs during the summertime for kids 15 to 18 years old,” he says. “We regularly visit Greenport, Block Island, Newport, Jamestown, Bristol and Fishers Island, and on the 10-day trips we get to Nantucket and Martha’s Vineyard. We have participants with a wide variety of experience levels, and we teach what you need to do to sail the boat and live aboard comfortably. Our program emphasizes seamanship and teamwork, and everybody who sails on Brilliant becomes part of the crew and shares the duties.”

“I’m a firm believer that the structure of each day is important, so each morning we clean the boat and get her ready to sail before breakfast. We sail for about 12 hours, then either anchor or go dockside each night. What we’re really teaching is life skills. It takes a lot of patience to live with 11 other people on a 61-foot boat, and things like communication and responsibility happen naturally because that’s what running a boat properly and safely demands.”

“We break each group into watches. I lead one watch and the mate, Chris Jander, leads the other. When we’re sailing we have a bow watch, a navigator, a log keeper and a helmsman. We rotate those jobs every half-hour, and build on the skills that we teach as the week goes on. The navigator might start with circling buoys on the chart as we go by and recording a time, and by week’s end he or she is charting course lines and three-bearing fixes, plotting GPS positions, and calculating our ETA. The log keeper writes down everything that’s happening, including weather observations, speeds, courses and location, and I encourage them to do a narrative: ‘What do you see, hear and think while we’re sailing along?’”

“We figure that 10,000 kids have sailed on Brilliant in the last 62 years. She’s a wonderful teaching tool, and I love watching them getting into sailing the boat, especially towards the end of the week when they’re sailing her well, working as a team, and taking care of each other. The kids typically don’t know each other at the beginning of the week and they’re usually uncomfortable, and the bonding that takes place is amazing. Finding people who take care of each other as well as we do on a boat is sometimes rare in today’s world, and it’s really nice to see. There’s no denying that sailing changes people!”