After 27 years of building the wooden boats of other men’s dreams, Nathaniel Benjamin, 60, built a boat for himself.

They christened her Charlotte under parted skies on Saturday afternoon. Hundreds of onlookers spilled onto the beach, down to the end of the dock and up to a rooftop of the boat yard. The potluck was plentiful and the beer flowed from a rowboat packed with ice. Boat launchings mean big parties at Gannon & Benjamin and this was no exception.

A wooden schooner, she measures 50 feet on deck and 43 at the waterline. She has a 14-foot beam and a six-foot, eight-inch draft. Her hull is planked in silver balli and angelique — South American hardwoods from Suriname. She is framed in sawn black locust and angelique, with an angelique backbone. The spars are Sitka spruce and Douglas fir and the deck is teak.

Charlotte is a new boat, but pieces of her come with history. Her compass, her brass winches, her 8,000-pound lead keel and — not least — her name.

After speeches by Matthew Stackpole of the Martha’s Vineyard Museum, Mr. Benjamin and his wife Pamela Benjamin, a poem by John Maloney of Chilmark and songs by Kate Taylor and Devan Donaldson, a past member of Vineyard Sound, the 56,000-pound vessel eased down the railway and floated — somewhat reluctantly — off her cradle into Vineyard Haven Harbor. Not yet rigged for sailing, she took her maiden spin around the harbor with an 80-horsepower Cummins diesel.

rowing to the sailboat
Charlotte sets out, still unrigged, in Vineyard Haven Harbor. — M.C. Wallo

The schooner took three and a half years to build, but her design had been gestating in Mr. Benjamin’s mind for 20 years before he sat down to make the first sketches in the late Nineties.

“When Ross [Gannon] and I started the boatyard [in 1980], one of the things we discussed was that we would be able to build our own boats,” Mr. Benjamin said. “Well, it took a little longer than we thought. Mine’s going in the water today, and his is well along.”

Sitting on the side porch of his Vineyard Haven house on the morning of the launch, watching the rain pour down and the schooners race on the distant harbor, Nat Benjamin reflected on the journey that brought Charlotte into the world.

“I’ve always liked the schooner rig and I thought someday wouldn’t it be fun to build one for us,” he said. He had sailed on an old, wooden Alden-designed schooner called Madrigal in the late Sixties and in 1969, he sailed a Block Island schooner across the Atlantic. He also sailed on a friend’s 40-foot Tancook schooner. But in 1974 or 1975, a 50-foot schooner named Voyager sailed into Vineyard Haven harbor.

“I thought, boy, this is just about the right size. It’s big enough to go anywhere but small enough to maintain,” he said. Voyager weaved its way into the plans growing in his mind.

crowd on dock
Hundreds of spectators line pier for launch. — M.C. Wallo

The next ingredient arrived in 1995 when a man by the name of Dan Adams bought a 52-foot wooden ketch in Florida without a surveyor’s report. He hired Ross Gannon to bring it up to Gannon & Benjamin for restoration. The boat leaked like a wicker basket and further inspection revealed it was so rotten, it would have to be completely rebuilt.

Faced with that expense, Mr. Adams opted to commission Gannon & Benjamin instead to build the true boat of his dreams — a 65-foot schooner. (Mr. Adams went bankrupt mid-way through the project, a story documented in Michael Ruhlman’s 2001 book Wooden Boats.)

Mr. Benjamin was able to salvage a key piece of the rotted ketch — its 16,000-pound lead keel.

“I looked at that keel and thought, that would look just about right on the bottom of our schooner,” Mr. Benjamin recalled. He added it to the design in his mind.

Then about 10 years ago, he received a phone call. Someone had found a boat in a field in New York, rotting after years of neglect. The name was almost entirely worn away, but there was no mistaking it. It was the Sorcerer of Asker — the old racing sloop that he and Pam bought in Gibralter in 1970.

“It was a 1921 Johan Anker. It was 38 feet along the waterline and 60 feet on deck. It had a narrow beam of 10 feet and drew almost 8 feet. It was originally built as a 10-meter class,” Mr. Benjamin said. “Very fast, very wet, but a blast to sail.”

After a year in the Mediterranean, a year in the Caribbean and myriad adventures, they sold the boat after settling on the Vineyard in 1972. About 25 years later, he paid $100 for what was left of it.

Mr. Benjamin traveled to New York with a friend and salvaged the two brass Lewmar winches, some hardware and the beautiful Sestrel compass that was put on the boat when it was rebuilt in England in the 1950s.

“I did two transatlantic crossings on Sorcerer, so I spent a lot of time looking at that compass. So I am just thrilled to have it on Charlotte,” he said. “It’s nice that there’s a continuum, that’s very meaningful,” he added.

The two friends then cut up the boat and gave it a proper Viking funeral, lighting it afire in the field.

“By that time, I really did have this in my head. When I sat down to draw the boat, it really didn’t take that long,” he said.

But beginning to build a 50-foot wooden schooner is not something done on a whim.

“I certainly consulted Pam and our kids to some extent. They were very encouraging and said ‘go for it,’ which was pretty incredible in and of itself,” he said. “A lot of families don’t have that kind of support.”

They might have said, “What about college tuition?” or “What about the house?” But they didn’t.

“It’s different when you’re building it for yourself. There’s a major financial issue of course — I actually have to pay for this stuff, rather than being paid for it,” he said. But that was the dream.

“You only go around once. You may as well make the most of it,” he said. “It’s the process of building it that’s fun — the journey, not the destination. And not just the process of building it, but the people who are involved with it. That’s what makes it so enjoyable.”

There was a short window of time after the launch of Juno in 2003 to use the floor space to loft Charlotte, meaning draw the boat out full-size and make patterns.

“Then we had to be out, because we had another boat building contract,” Mr. Benjamin said. “I didn’t know if I’d be building it right away.”

He did have the lumber and hardware on-hand, purchased and collected over the years. Then, in January 2004, he got a call from friend and fellow sailor Geoff Gibson.

“He said, ‘My son Tyler’s not doing well in high school,’” he recalled. He asked if Mr. Benjamin could give Tyler a job.

“My first reaction was no, but then I called back and said maybe he’d be interested in this project for our family,” he said. “Tyler really caught fire and got into it and started chopping out these big timbers. Then we got into cutting frames. He has this unusual talent to be able to look at a drawing and comprehend bevels and irregular shapes that you have in a boat. He was a very quick study. I was helping him when I could, but I was busy with other boats in the yard.”

Tyler worked for over a year, building all of the backbone timbers and sawn frames. From then on, Charlotte always had one or two people working on her — people like Chris Rockwell, Bill Benns, Thomas Stackpole and dozens of others, as well as Mr. Benjamin himself.

The name came about six months ago.

“Charlotte was my grandmother on my father’s side. She was an adventurer for sure. She and her husband used to go on these epic canoe trips in the Twenties, hunting and fishing in the Canadian wilderness with Indian guides,” Mr. Benjamin said. “She was matriarch, not only of our family, but our whole town, which was a Hudson River town. She was very dignified and at the same time very compassionate. She was very supportive to me. I had, I guess you could say, a checkered career growing up and she was always very helpful to me.”

Mrs. Benjamin suggested the name Charlotte.

“As soon as she mentioned it, I said of course,” he said. “Not only is it a beautiful name, it has such a powerful meaning. Pam knew her. She knew what a strong person she was.”

Charlotte will stay on a mooring in the inner harbor through the winter. Myles Thurlow will do all the rigging this fall, before it snows. There are still shelves to build and some plumbing and wiring to do before she is ready to travel. But travel she will, with 250 gallons of fresh water, 100 gallons of fuel and sails with infinite range.