Q&A: What's Eileen Up to Now? Like Jimmy Buffett, She Bought a Trawler (Audio)
Wandering Minstrel of the Islands Reflects on a Niche Music Career
For 12 years, Eileen Quinn was the wandering minstrel of the Caribbean, accompanied by husband David Allester aboard a Bayfield 36. She used her music to paint a picture of cruising life. Unlike Jimmy Buffett and his happy band of imitators, her lyrics went beyond margaritas and tropical merriment. She wrote a collection of songs that, taken together, create a uniquely accurate portrait of a subculture. She wrote about the joys and angst of boat ownership and what happens when North American suburbanites—many of them retirees—flee down island trying to escape their suburban fates.
Her songs are extraordinarily well written, full of wit1 and poignancy. You can find them on many of the streaming services and YouTube. Her observations continue to be relevant today. Alas, she has quit writing this kind of stuff, or we surely would have hilarious takes on today’s onboard tech obsessiveness and the current crop of YouTube “adventure” sailing channels, both of which invite parody.
Loose Cannon: Sometimes in Florida one gets the impression that all Canadians are sailors, and they're all down here. I happen to know that is not the case. How did you and David come to sailing?
Eileen Quinn: Forty years ago, David got talked into buying a boat in Vancouver with two buddies to go on a grand sailing adventure. One of them made it to San Francisco, the second to New Zealand, and only David made it back to Canada. So I married him. He talked me into life on the water, but it didn't take much convincing.
LC: Oh! I never realized that you were officially married, a mistaken assumption based on last names. Weren't you two working for the Canadian government before you went cruising?
Eileen: David never took my last name, so I understand your confusion. We actually met in Toronto when he returned from cruising the Pacific. He was a city planner and I was working with a city councillor. He continued working with the city but I left to work in community mental health planning and then ended up as the chief of staff with a cabinet minister in the Ontario government.
LC: So, here you are, firmly ensconced in "The Establishment" and you up and decide to become sea gypsies. What gives?
Eileen: David already had the bug and was eager to get back out there. Although I wasn't a boater, I loved the water, and I loved travelling. Both David and I had done some pretty adventurous land stuff before we met.
So, we committed to a serious ten-year plan to get our acts together financially but, halfway through, we decided we shouldn't assume we'd be alive that long. People in my family tend to live a tediously long time, but David's family is short lived. Crappy genes. And neither of us wanted to be able to look far down the road and see our lives laid out neatly ahead of us. Change is good!
LC: What were your ages when you set out?
Eileen: David was 41 and I was 34.
LC: Tell me about the boat. A Bayfield?
Eileen: A Bayfield 36. No speed demon but seaworthy and a good liveaboard. And it had a bathtub! Never got used for that, but it was a great place to keep the music equipment. Not sure how pleasant we smelled, but the sound system didn't get bashed around that way.
LC: A tub? Just like Lynn and Larry Pardey. At least you had an engine. And instruments. You were already musically inclined then?
Eileen: Oh, now don't be cruel. Little Gidding was a comfy beast. And not only did we have an engine, we had a head. Have to admit that I was a big Pardey fan until I read about their bucket.
We left Toronto with a guitar on board. Music has always been an important part of my life. But it took cruising for me to discover that I loved writing songs.
The first little combi amp we bought in Panama (where you can find anything your little heart desires). Later, we graduated to a proper sound system. And I made a cover for the dinghy so we could transport that stuff to the beach.
LC: Technically, you would be a singer-songwriter, I guess. Which do you think of yourself as most—musician or writer?
Eileen: I was definitely more of a writer than a musician then. But I've learned to play the harp since those days, and that's upped my musicianship.
LC: Stats time. How many songs have you written? How many albums?
Eileen: Five albums. So that's probably 60 songs recorded. Perhaps another few dozen written on top of that?
LC: I believe the music industry calls that "prolific." And I would call it “a lot of work.” Writing, arranging, recording, rehearsing, performing, etc. All for a niche market with a worldwide audience of what? 30,000 people? What was your motivation?
Eileen: In the indie music world, niche is really the only way to go. Derek Sivers, who founded CDBaby in the late 90s, liked to use me as an example of a niche market when he was promoting his site.
As for motivation, writing ideas down has always helped me figure things out. And music combined with words is a pretty powerful medium. Cruising involves a lot of down time; writing songs was a good way to fill some of that. Then I started playing in front of people and was shocked to find they listened and laughed and teared up and clapped. And then I made albums and people bought them. All of that combined to be pretty motivating.
I lost that motivation when I felt like I had kind of exhausted what I had to say about life on the water. When I stopped having something interesting to say, it was time to stop doing it. But it was a blast while it lasted. And the music is still out there on streaming services. The best thing about that is that I get to check out where the listeners are—apparently my fan base is stronger in the Netherlands than Canada. Who knew?
We were also really lucky to be doing this during a particular sweet spot in the development of technology. Recording had become affordable, and the web allowed for independent distribution. Perhaps most importantly, people didn't think of music as a free commodity then. I don't know how small-time musicians manage now.
LC: Beat me to it. I was going to ask you whether you thought you had basically run out of worthwhile subject matter. I always like the fact that there was basic truth in your songs, absent in the work of the world's Jimmy Buffetts (though I think he's alright). Plus, they were pretty effing funny. Did you have any particular favorites among your songs and albums?
Eileen: I'll take "basic truth" and "pretty effing funny" as high praise. Certainly, what I was aiming for.
I don't know if I'd call them favorites, but some are more memorable than others. Funny songs like “The Anchoring Dance” and “If I Killed the Captain” always got a really fun response. But for me it's the ballads that have the most staying power, like “Get Me Through This Night” and “Building a Boat.” I guess I like the Degrees of Deviation and Mean Low Water albums more than the others.
LC: I loved "Building a Boat." When I was a kid, someone took me to the other side of town where a guy had been building a boat in a barn for years. I don't know what happened in his case. I hope they both made it to the water. Those stories are out there, a basic truth.
As I recall, you guys dropped out of the cruising scene rather abruptly. What happened?
Eileen: My dad had Alzheimers and we had been spending a couple of months off the boat every summer living with him and my mom so that the rest of the family could take a break. We decided we needed our own nearby land base after a few years of that and bought an unfinished cabin as close to them as we could afford. Then the year after that we just decided we were done with full time cruising. In retrospect, we probably wouldn't have gone looking for some land if we hadn't been getting ready, at some subconscious level, to make the change. I don't think it was particularly abrupt, but perhaps it seemed that way because we're not into social media. I'm so lucky I had that last year with my dad.
LC: I did not know. That was the story of my grandmother, too. When did you swallow that anchor, and how long had you been cruising by then?
Eileen: 2006, 12 years.
LC: Gawd! You’ve been gone—so to speak—so long! What? Seventeen years. What have you two been up to?
Eileen: We spent a year making our little cabin into a home. The first few summers we captained a sailboat for a wilderness at the gateway of the North Channel in Lake Huron. We were both getting some training in those years as well—David in Emergency Management and me in Palliative Musicianship. David worked with the Red Cross. I played live music at the bedside at end-of-life in different settings. Eventually I ran a hospice for a couple of years. Then we bought an old pocket trawler and moved to Brockville.
I got bored in the pandemic and went back to work as a grief counsellor at the hospital a couple of blocks away. I'm leaving that in a couple of months, and we plan to spend the summer heading up through the Trent Severn Waterway to Georgian Bay and the North Channel. David does some online teaching for the Canadian Power and Sail Squadron and volunteers at the local food bank.
LC: So, like Jimmy Buffet you “bought a trawler.” What song was that line from?
Eileen: “Where Have All The Pirates Gone.’
LC: Well, you were never pirates, were you? Dare I say it, earnest Canadians—cynical yet somehow altruistic—bringing merriment to retired and not-so-retired gringo cruisers. I first saw you at the ranger's cabin at Warderick Wells around 1999.
I don't suppose you'll ever take that Windy 26 south?
Eileen: No, never pirates. Can we be cynical and earnest at the same time? Maybe that's where humor saves us.
I have to admit to a little heart stab when I think of Warderick Wells. Green clouds and groupers. I sure miss the Bahamian beaches.
But as for taking Bob (our Windy 26) south—probably not. There is a lot of excellent cruising to be had here in the summer months. And we'd miss the snowshoeing (but not the shoveling) in the winter months. Now that's an earnest Canadian response.
LC: Do you have a message you'd like to send your fans?
Eileen: Thank you for listening. If there's a beach nearby, walk it for me.
LC: Thanks, Eileen. My best to David...and Bob the Trawler
Eileen has released five CDs: No Significant Features, Degrees of Deviation, Mean Low Water, Not To Be Used for Navigation, and Miss Inclined.
From “If I Killed the Captain,” album Mean Low Water:
I spoke those words most truthfully. I took them to my heart, Especially that line about 'Til death do us part. But if I killed the captain, Really, who would know. We're two weeks out of port. We've got one more week to go.
From “Where Have All the Pirates Gone?” on the album Miss-Inclined:
Where have all the pirates gone? They're pumping gas in Marathon. Living in some trailer park, They sail their dreams out after dark. Time flies--You can't stall her. Jimmy Buffet bought a trawler.
From “The Golden Age of Sail,” on the album Mean Low Water. This song was revenge parody after Eileens songs were disqualified from a sailing music competition for not being sufficiently “traditional.
The golden days, the golden days of sail, When the cabin boy feared the captain's wink And we all crapped over the rails. Ah the days when men were men, And women stayed at home. Adventure drove the sailors Upon the seas to roam. We cut such dashing figures. Romance filled our lives As we brought great sport to every port And syphilis home to our wives.
Hey Pete wanted to post a comment on the quinn story but forgot that I have never been able to sign in. Maybe you can post it for me
I have very fond memories of Eileen doing a "concert" for one of the Great Harbour rendezvous. She did a song about a guy that knows he is dying and takes one last trip by himself, leaving his wife behind. I can remember working hard to not let anybody see me shed a tear over the story she told in her song! Great performer! Where can we buy the CDs?
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I love it. Would you be interested in playing for an SSCA Gam in Melbourne FL, Nov 16, 2025? Huge fan. Donna Lange, 2 time solo circumnavigator SV_ Inspired Insanity.