Everyone knows it’s hard to break into the music business, but Bob Tassi of Rockport, former director of studio operations for Warner Bros. Records in Nashville, knows something else again. After being part of the remarkable singer/songwriter surge that Music City went through in the 1990s, the captain and owner of the Timberwind is quick to say the schooner business “is the hardest thing I’ve ever done, by far.”

This summer, Tassi is combining his past and present careers with a series of Down South Meets Down East acoustic music cruises featuring notable singer/songwriter colleagues from his Nashville days. The first two cruises, with Kevin Welch and James Dean Hicks, are close to sold-out, and more will be added to the season’s schedule as the connections are made.

Given the way the Nashville scene changed shortly after Tassi left it behind, it seemed that life was gone forever. But he recently began writing songs again, and Facebook provided a way to reconnect with people he had worked with including Welch and Hicks. Both began as songwriters — their hit output includes “Till I’m too old to die young” (Welch) and “It takes a little rain” (Hicks) — and became successful as performers and recording artists. Welch has just released a new CD of original tunes, “A Patch of Blue Sky,” which is climbing the Americana charts. Hicks, a performer since age 10 whose songs have been covered by everyone from Conway Twitty to Jessica Simpson, also has a recent album, “Making My Own Way.” Both men tour regularly.

Tassi, who grew up around both boats and music in San Francisco, had been a songwriter/artist in his home city with his twin brother and originally came to Nashville as a performing duo. The San Francisco music scene had changed as California rock evolved into punk —”too loud and angular for me,” said Tassi — the recording industry vacated the Bay Area for other locations. Nashville was just moving out of its “Urban Cowboy” phase and change was in the air there, as well.

“I’d already lived in a big city, so wasn’t interested in New York and definitely not L.A. I wasn’t a big fan of country music, but I understood it and felt I could participate in it,” Tassi said.

Somewhat on a whim, he headed for Nashville. As it turned out, several hundred other songwriters from both the East and the West headed there too “and a window opened for us, for some reason,” said Tassi. He and the other arrivals ended up defining the next era of Nashville — the singer/songwriter era.

As he learned the ropes of the town, hanging out at the coffee shops and writing songs, Tassi said he fell into a position at a recording studio and ended up the assistant engineer at the renowned SoundShop, a great place to learn the recording trade and meet people. One of the people he met was the president of Warner Bros. Records. Tassi ended up being his personal recording engineer.

“I was the spoiled brat kid at Warner Bros.,” he said, but got away with it because he turned out to have a facility for helping turn some “talented kids” into big stars. Making demo recordings led to a lot of professional friendships, due to the nature of the work. Take Welch, for instance, who Tassi said even as a young staff songwriter had wisdom, insight and a little fire, as well as being a phenomenal talent.

“We didn’t have a personal relationship, but you make a strong connection working on music because recording is such a personal thing — James was the same way,” he said.

Both men became artists, because they respected and personified “the hub of what was going on then — three chords and the truth,” said Tassi.

It wasn’t going to go on forever, however, and when Tassi and his Maine-born wife Dawn spent a vacation week aboard the Stephen Taber in 1998, he started thinking about the Maine-coast schooner industry.

“Wow, I thought, this could be an incredible thing to do,” he said — which is why, the next summer, at age 44, he became a deckhand on the Stephen Taber. Taking summer breaks form Nashville, he worked his way up to First Mate, then became the acting Captain of the Timberwind and, in 2002, its owner.

“Thirty-three days after I signed the papers, she sunk,” he said, referring to the vessel’s taking on water due to ice damage in the winter of 2003.

Tassi had engineered two Grammy Award-winning albums during his time in Nashville and reaped the rewards, but he knew it was only a matter of time before the city’s expansive music industry began to contract. Then the corporate office in Burbank got wind of Tassi’s second career and it was time for him to make a choice.

“I always thought I could slip back in, but I’d have to start my way up all over again and I wasn’t going to do that. There was no going back,” Tassi said.

Running a seasonal schooner business has always been a risky proposition, and the decade Tassi has been at it has boasted some very tough economics. The Timberwind, built in 1931 in Portland, needed a lot of work and has had almost a complete rebuild under his hand. But Tassi said he doesn’t regret leaving Nashville behind; well, maybe he has one regret.

“I didn’t save my money like I should have,” he said.

The Down South Meets Down East Music cruises are one way to add a new wrinkle to the venerable seasonal cruise gig, something every Midcoast schooner has to be creative about.

“But you really can’t make a bad choice in this fleet. Everybody knows what they’re doing and they do it well,” he said.

Last September, Tassi unexpectedly returned to something he used to do very well. He was awakened in the middle of the night by a song, which he did his best to write down. It was his first song in 13 years.

“My music is alive in me again and it wants to come out,” he said.

One of the people he told about the song was Welch, whose informal playing during a cruise last season provoked the idea for the singer/songwriter cruises.

“I told him it came to me clear as day, and he said ‘Now you have to make it clear to the rest of us,'” Tassi said.

It has yet to be made clear if the Down South Meets Down East cruises are a smart idea for the Timberwind, but the response to the first two is encouraging. Tassi thinks word will get around, not only among prospective passengers but also among the musicians of his old haunts.

“Who doesn’t want to come to Maine in summer?,” he said.

The Hicks cruise is set for Friday through Sunday, July 22 through 24; and the Welch cruise is Monday through Thursday, Aug. 22 through 25. For reservation information, call 800-759-9250 or visit schoonertimberwind.com, where additional music cruises will be posted as they are scheduled.

VillageSoup Art/Entertainment Editor Dagney Ernest can be reached at 207-594-4401 or by email to dernest@villagesoup.com.