On a hot and sunny July afternoon, with the sun glinting off Lake Champlain, Cory Dalsimer ’21 stands next to his two timeless sailing sloops, the Friend Ship and the Wild Rose. A few minutes later, both boats are slicing through the water, filled with passengers smiling into the wind. 

It feels timeless. But this moment - like the business behind it - is something Cory is learning to steward and grow. One sail, partnership, and problem at a time.

Cory, a 2021 graduate of the University of Vermont’s mechanical engineering program, is the sixth owner of the Whistling Man Schooner Company, a Burlington sailing charter that has become both a beloved summer fixture and a quiet engine of community connection. 

His story is as much about grit as it is about boats.

“Back in 2018, I sent an email out of the blue,” Cory remembers. “I said, 'My name's Cory. I love sailing. I'd love to become part of your crew.' They wrote back and said they weren't hiring. But I asked if they'd meet me for lunch anyway.”

The owner of the company said yes. That conversation turned into a job. That job turned into an education.

From Shore to Ship

Cory grew up in Vermont and started his college education at Vermont Technical College. He transferred to UVM to get his four-year degree and began working for Whistling Man in 2018 while still an undergrad. 

He started with maintenance and deckhand work, quickly gaining skills and sea time. “I was going to school full time and working on the boats in my spare time,” he says. “It was a good balance - working with my hands and challenging my brain.”

He stayed on after graduation, eventually earning his captain’s license and stepping into a leadership role. Over time, he entered into conversations with the then-owner, who had already modernized much of the business. 

When the chance came to take the helm himself, Cory said yes.

Getting there wasn’t easy. “I didn’t have any money to my name,” Cory says. “I remember filling out the loan application and asking if I should list my 1998 Honda Accord and my cat as assets.” 

With help from the previous owner, the Vermont Economic Development Authority, and a regional bank, he was able to pull together the financing needed to buy the business

Not Just a Boat Ride

Since taking over, Cory has expanded operations to the largest crew size ever with more offerings than ever before. Many of the crew are UVM alumni, and several have become captains through a mentorship program that helps new sailors earn their licenses - with course costs covered by the company.

“I see it as an investment in people,” Cory says. "We have folks who where I was eight years ago, diving into a maritime career with WMSC.” 

That sense of stewardship extends beyond the dock. Whistling Man partners with local musicians for tiny boat concerts, and has collaborated with UVM, state tourism groups, and local organizations on community events. 

One highlight: participating in Burlington’s Juneteenth celebration. “That day really filled my heart,” he says.

Legacy and Learning

While the name Whistling Man Schooner Company might raise eyebrows (there is no whistling allowed aboard - an old sailor superstition), its reputation is deeply rooted. “This business has been a part of Burlington for decades,” Cory says. “I’m just the sixth owner. I see myself as a caretaker more than anything else.”

He credits UVM for giving him the mindset to succeed. “The mechanical engineering program was the hardest thing I’ve ever done. It taught me how to think my way through complex problems. That shows up every day in this work.”

From designing efficient systems for boat maintenance to managing staff schedules, Cory sees the overlap clearly. “It’s all about building systems that work and knowing how to adapt when they don’t.”

Sailing Forward

Today, Whistling Man is on track for a record-breaking season. They've been featured in Yankee Magazine and Stuck in Vermont, among other publications and accolades.

But for Cory, the real reward is local.

“At the end of the season, when I go through bookkeeping, I think, this is our little slice of the Burlington Economy. From payroll to vendor costs, taking around 5,000 passengers for a sail on Lake Champlain is a big impact to Burlington. That feels really good."  

As for what’s next? Cory isn’t ready to share details, but he hints at big plans. “We’re working with UVM, the State of Vermont, Hello Burlington. There’s so much potential for growth.”

For now, he’s happy with where the wind is taking him. “Come out for a sail,” he says with a grin. “It’s a good place to be.”

Learn More

You can learn more about Cory and the Whistling Man Schooner Company at their website.Here are a few more alumni stories that showcase our incredible Catamount community:

• Olivia Weale '19 Makes Dam Good English Muffins

• Class Notes Expanded: Karin Tilberg '78 Loves the North Woods

• "It Feels Like Coming Home": Cathy Irish Tremblay ’85 on the Power of Staying Connected to UVM