There is a certain serendipity to Venture’s long voyage. For most of her 106 years the wooden gaff-rigged sloop was simply a part of Vineyard Haven Harbor, fitting into the seascape as much as Shenandoah or the town dock or the ferry terminal.

Through the many generations of sailors Venture has owned, she has seen good times and bad times, left home for a while and ran into a bit of trouble, changed some, and then changed back. But the most serendipitous development of all is that she is back in Vineyard Haven Harbor. How she got back here is quite a tale.

“They have their own lives, their own destiny,” said Nat Benjamin, who owned Venture for many years. “The owners come and go and the boats go on and on and on. All they need is good caretakers.”

Steve Myrick

Venture’s current owner, commercial real estate entrepreneur Karl Frey, will sail her for the final time in the annual Moffett Race this weekend. During the following week, he will sign the papers to sell the boat to Danny Braunstein, director of a storied engineering lab at the Massachusetts Institute of Technology.

Mr. Braunstein will sail her the following weekend in the Pat West Gaff Rig Race. The namesake of the race is a legendary sailor in these parts. He got his start on the water on the very same boat, working aboard Venture as a teenager. He bought the gaff rigged sloop in 1933, and sailed her for 50 years.

“Wouldn’t it be neat,” Mr. Braunstein said recalling the genesis of the well timed sale, “if Karl finished his tenure with the Moffett, and we launched ours in the race named after her owner. It just felt right.”

How’s that for serendipity?

From the start, Venture seemed to draw affection from everyone who happened upon her course.

“Charters paid for my education,” Mr. West wrote in a book about his boat. “I loved that boat. She was my moveable apartment, my source of income, my source of fun and my refuge in troubled times.”

When Mr. West got on in years, he could no longer give the wooden vessel the care she needed, so he gave the boat to someone who could, on the condition that he restore Venture to all her glory. Mr. Benjamin was just starting his wooden boat business on the waterfront. He spent a few years getting her back into shape, and adding, with care, his distinctive design touch. Then he sailed her for the next 30 years with his growing family.

The latest chapter, however, doesn’t begin with Venture. It begins with Valora.

Valora was designed by David Stimson and his son, and built in the Boothbay Harbor Shipyard in Maine. She was built for Mr. Frey, and the boat was in Vineyard Haven for several years. As Mr. Frey described it, Valora attracted a community of admirers who sailed her and cared for her, while becoming fast friends.

During a vicious northeast storm in August 2010, Valora broke loose from her mooring in the outer harbor, and in a heartbeat she was up on the breakwater, with the relentless swells smashing her to unrecognizable bits of splintered wood. The community was devastated. As Mr. Frey walked the beach about a week later, he spotted one of those splintered pieces of Valora. It brought him to his knees. A month later, at a gathering of Valora’s crew, Mr. Stimson approached Mr. Frey.

“He told me we’re going to build a bigger boat for half the price,” Mr. Frey said, recalling the conversation. “Then he rolled out the plans, he had already drawn it.”

So they embarked on a five-year plan. The design was sturdy, but spartan. Mr. Stimson would build the boat at his shop in Boothbay Harbor when he could fit in time around his other projects. But five years is a long time to be out of the water if you’re a sailor. So about a year later, Mr. Stimson approached Mr. Frey again. He had kept track of Venture, and she needed help.

Venture is a 106-year-old gaff-rigged sloop. — Steve Myrick

“She was languishing in Portland [Maine] at the dock,” Mr. Stimson said. “She was structurally in fine shape, but the paint was peeling, the varnish work was gone. I talked him into buying Venture to have a boat while we finished this schooner.”

So Venture acquired new owners. Mr. Frey’s name is on the paperwork, but Mr. Stimson and professional skipper Lu Yoder are part of the family.

“Like all 100-year-old boats, it needs a lot of work,” Mr. Yoder said. “We’ve done some things to bring it part way to a condition that will allow it to last another 100 years. It’s smart to have a boat in the water. Then you don’t rush, you do the new boat right. Having a boat in the water keeps it fresh in your mind how brutal and punishing the sea can be, so you build the new boat really strong.”

Mr. Braunstein, who spends much of the year at his home in Vineyard Haven, was infected with the wooden boat bug while building a skiff. He intended his next project to be a much larger boat, and had sketched out a plan that would involve eight years of work on nights and weekends. But he changed course when an advertisement in the Vineyard Gazette caught his eye. With the new boat nearing completion, Mr. Frey was ready to sell Venture. Mr. Braunstein rowed out to Venture one day to take a look. Mr. Yoder happened to be aboard. They talked about the boat all afternoon.

Some time later, he went out for a sail, on a day that started with very little breeze.

“I love the sound of a diesel engine,” Mr. Braunstein said. “When we killed the diesel, you could hear the water lapping against the hull. The sails were luffing, then you heard them pop, because the wind came up. The change from the sound of the engine to the sound of the sails, I just thought, it doesn’t get any better than this. Lu turned to me and said, grab the wheel. I know it’s the easiest job on the boat, but it was just terrific, just the feeling that it may become part of my family, I was delighted.”

Parting with Venture won’t be as sad a day for Mr. Frey as it will be for Mr. Stimson and Mr. Yoder.

“If I loved the boat, then it would be really tough,” Mr. Frey said while sitting in the ample cockpit of Venture on a glorious sunny day last week. “Is it awful for me to say I don’t love the boat? I loved Valora. I’m going to love the new schooner. This boat was a wonderful placeholder to keep the community around Valora together. Lu loves the boat, David loves the boat.”

The three men have formed an extraordinary friendship, held together over the years as tight as the planks in the wooden hulls they have shared. It’s as strong and reliable as the swift current that ebbs and flows in Vineyard Sound.

“I work in an office in Manhattan,” Mr. Frey said. “When David sends me a picture of the new schooner under construction, or I get an email from Lu, it changes my whole day.”

“It became clear to me after working for Karl for six or seven years,” said Mr. Yoder, “that he’s very interested in the tradition of sailing wooden boats, and getting the sailing part right, and the technical part right. But that takes second place to what kind of relationships you build. A hundred and fifty years ago, when people worked in the sea in boats, they looked after each other and they survived by teamwork.”

For more than a century Venture has been owned by people who love her. — Steve Myrick

“A well built wooden boat,” Mr. Stimson said, “if it is taken care of, will last longer than any other construction method. As long as it’s built well to start with, one plank, one frame, the keel, pieces can be replaced individually. The older wooden boats have a beauty and an appeal that other boats don’t have, so it makes people take care of them more.” All along, the plan was to sell Venture when the new schooner is ready to sail. There is still much to do, but launch of the new boat is scheduled for next spring.

Mr. Frey has an altruistic streak. He will sell Venture for much less than the purchase cost and the subsequent cost of restoration. The value for him, is that Venture stays in Vineyard Haven.

“I’m not a wealthy guy, but I love to do the right things,” Mr. Frey said. “Selling this boat to someone like Danny Braunstein is exactly the right thing. Everything happens for a reason. He’s just the right owner for this boat.”

So it looks like a win, win, win, win situation for four men who love their wooden boats. There is an old idea among old sailors, that a wooden boat is made from a living thing, and when the tree is cut down to make the boat, it dies but its soul goes into the boat.

Venture has been fortunate now for more than a century to be owned by people who understand her soul.

Or maybe, it’s the other way around.

“You never really own a boat,” Mr. Braunstein said. “We’re going to be owned by the boat. And that’s fine.”

The 39th annual George Moffett Race takes place on Saturday, Sept. 10. For more information visit