In the fall of 2019, Vermont natives Hannah Miller and her partner Erick Tichonuk decided to buy the Greenport-based ketch sailboat “Surprise” — and the sailing charter company that came with it — from local captain Pat Mundus. The following spring, they were hit with a less welcome surprise when COVID-19 swept the globe.

“We started in 2020 and we had one of those crucial decisions to make: ‘Do we try to go into business at the beginning of a pandemic? How’s that going to work?’” Mr. Tichonuk said this week. “April and May [2020] were terrifying months. Nothing was happening.”

But by summertime, as restrictions began to loosen — on outdoor activities, at least — business started to take off and ultimately the couple ran 120 charters that first year. Last year, they bought a second boat to meet what they said is a growing demand for public and private sailing charter cruises on the North Fork.

“It ended up being a good business move, because all we did was private charters,” Mr. Tichonuk said of their pandemic gamble. “And so it was a great start for us.”

The couple had been working in New Zealand when the pandemic took hold.

“We had a choice,” he said.“We could have stayed in New Zealand, which arguably was one of the safest countries at the time for COVID, or return to COVID central [New York] and attempt to start a business. Let me tell you, there was some soulsearching.”

The pair purchased “Surprise,” a 1967 F. Spaulding Dunbar ketch sailboat, from Ms. Mundus, a beloved local captain and daughter of world-renowned shark hunter Frank Mundus. The restored 57-foot ketch features longleaf yellow pine bottom planking, mahogany topsides and white oak frames. Along with the boat came Ms. Mundus’ East End Charters, launched 15 years earlier.

The couple met while both were working for the Lake Champlain Maritime Museum in Ferrisburgh, Vt., on a five-month tour aboard a replica 19th century schooner. Mr. Tichonuk had worked for the museum for 30 years, while Ms. Miller got involved in sailing more recently.

She had led white water rafting and kayaking and canoeing trips in New England, “but I had always wanted to learn to sail,” she said this week aboard their newest boat, the “Bonnie Lynn,” a steel-hulled 72-foot schooner with a 32-person capacity.

She found a four-month training program on a 150-foot square rigger with 27 sails, and never looked back.

“I dove right in,” she said of her experience learning to crew, make sails and repair boats.

As soon as Ms. Miller felt she’d gained enough experience, she began crewing on a variety of vessels. “I would go on any boat that anyone would take me on,” she said.

Ms. Miller continued recreational sailing and crewing on boats before she was hired to crew for a five-month tour on the Vermont museum’s replica of an 1862 Lake Champlain Canal Schooner, a type of canal boat built after the canal was expanded that year to make room for larger vessels.

“When you spend five months on a boat with someone, you get to know them really well,” she said.

It was the longest sea voyage to date for both sailors, and it convinced them that they wanted to live on the water.

“We ultimately said, ‘This is the perfect way to get into living aboard [a boat] full-time, and being able to support that lifestyle with charters.’” It’s now been more than five years since the couple has lived on dry land. For the last four years, they’ve lived aboard “Surprise,” docked in Greenport every summer and in the Bahamas each winter.

Mr. Tichonuk said life on the sea is a perpetual adventure.

“You wake up in the morning and you step out on deck and you just feel good. You’re in the moment and you’re outside. We’re very in tune with what the weather’s doing,” he said. “It dictates our life, but that’s so fun. There’s a rhythm to that.”

Last year, the couple upped their charter game with the purchase of the “Bonnie Lynn,” which has three guest cabins and two guest heads (bathrooms) in addition to the captain’s cabin.

They had planned to sell “Surprise” and pour the proceeds back into the business, but ended up selling to Charlie Beyer and Sarah Bell, a couple they knew from Vermont who were also looking for a lifestyle change after the pandemic. The four of them are now partners in East End Charters.

“I could have been content on ‘Surprise’ for many more years,” Mr. Tichonuk said.“But we bought [the Bonnie Lynn] because people were calling and saying ‘We’ve got 12 people. We’ve got 18 people.’ And we would have to say, ‘Sorry, there’s no boat on the North Fork that can accommodate that many people. You will have to hire someone from the South Fork to sail up to the North Fork to pick you up.’ And that never felt right.”

Still, there are challenges. “Owning a boat like this is like having an infant that never grows old,” Ms. Miller said with a grin. “You always need to keep an eye on it and [be] on top of it — or if you’re not on the boat, you need somebody else checking in on it.”

The couple said the welcome they’ve received from Greenport’s maritime community has made all the difference — and for that, they said, a lot of the credit goes to Ms. Mundus and the care she put into restoring “Surprise.”

“When you buy a unique boat, you inherit an amazing community around that boat,” Ms. Miller said. “Wherever you are in the world, it’s just — interesting boats attract interesting people. So [in Greenport], it really helped that Pat had [captained] “Surprise” in this area for almost 20 years. So when we bought the boat, there was this whole community of people that welcomed us because we had this boat that they all cared about and that they had spent time working on or sailing on or just seeing in the water,” she said.

“You always have to forge new relationships with people, of course,” she added. “But having that common point already made it really easy for us to come here and be welcomed in the Greenport area.”