Don Sullivan Sails Through Retirement

After retirement, some men drive around looking for things to do. Some drink beer. Some clean out their garage.

Don Sullivan drove for Uber. He brews craft beer. And he’s built 2 boats in his garage — the latest a 20-foot yawl.

All in the past 3 years.

He and his wife Dawn have lived in Westport for 41 years. They raised 3 children here. She was very active in Christ & Holy Trinity Episcopal Church, He says he was “somewhat” involved.

Don and Dawn Sullivan, in 2005.

After a career spent selling large technology systems to the publishing industry, Sullivan retired at 63. A gregarious “people person,” he began driving for Uber. It was fun, and he made nearly 2,700 trips. But he gave it up a year ago, when the novelty wore off and it became “a commodity.”

He and his friend Steve Knapp created a great-tasting beer. They named it Valley Forge Brewery. They just finished their 12th batch. Each is only 48 bottles. “We don’t sell it. We drink it,” Sullivan says.

But all of that pales next to his boats. His interest was piqued when he saw photos of Henk Hoets’ flat-bottom lumberyard skiff.

Don Sullivan

Though he’d sailed all his life, Sullivan had never given a thought to building a boat. In fact, he’d never built anything.

Suddenly though, he was motivated.

He bought plans and lumber, and went to work. Two months later, it was done. It’s now moored at Longshore.

That project done, Sullivan gave his tools away.

But at a 2018 boat show in Mystic, he saw a beautiful Caledonia yawl. It was there last year too.

So Sullivan decided to build it.

Constructing a 2-masted, double-ended sailboat is a lot more difficult than a skiff.

But Sullivan bought plans from a man in Scotland. He gathered all the tools he needed. He headed to a specialty lumber yard in White Plains.

Then he got to work.

An early stage …

“I just followed the plans,” Sullivan says, as if describing how Waze helped him get home.

“The plans” included putting planks over a mold — upside down. Then he flipped it over, and worked on the interior.

… a work in progress …

It took 500 hours, over 5 months. Much of that time he was on his knees, or in awkward, uncomfortable positions.

He worked alone. It was physically demanding — the planks are 24 feet long — and mentally exhausting too. “There’s a constant, anxious challenge of getting it done,” he explains.

But, Sullivan notes, “This was a calling. Driving home from Mystic, I knew I had to build this boat. And convince my wife of it.”

… nearing completion….

This project became the most enjoyable thing he’s ever done. “I’ve never been happier, prouder or more enthusiastic about anything,” he says.

The yawl launches in April. He’ll sail in local waters, then head to Cape Cod.

His wife will be on board — physically, and emotionally.

“We’ve been married 42 years,” he says. “It gets better every day.

“But this was not my finest moment. For 5 months I was constantly focused on this. Dawn was 100% supportive.

“Now I’m looking forward to doing things together again. She’s a great first mate!”

… and finally shipshape.

Sullivan does not know what his next project will be. He will not, however, build another boat.

Although, he admits, “I said that after the first one too.”

(Hat tip: Jeff Wieser)

8 responses to “Don Sullivan Sails Through Retirement

  1. Debbie Hoult

    Typo alert!

    Dong in there should be doing……I forget now where it is.

  2. Rindy Higgins

    Gorgeous boat! Fair winds, Don and Dawn!

  3. Kathryn Sirico

    Congrats! What an inspiring life and just a great story to wake up to.

  4. Anne Rutherford

    It takes a high quality guy to construct such a high quality vessel. Congratulations to you, Donald, and to your ever supportive First Mate.
    I’m so pleased to see you both celebrated for your dedication and perseverance, neither of which have ever been in short supply in the Sullivan household. Let’s toast you both with a beer!

  5. Quite an accomplishment. Retirement is the Renaissance of life.

  6. Fantastic story. As a fellow retiree, I have to say I’m a little jealous!

  7. Wally Woods

    This is not retirement……in fact it is living life to the fullest. Bravo, bravo. Keep on keeping on!

  8. Meg Freeman

    Contrats to you Don! Not only in your achievement but embracing your retirement too! May I wish you and Dawn many happy “sails” in this coming year and beyond. Meg Freeman