The author writes the “Resourceful Sailor” series of articles on the Small Craft AdvisorSubstack, which first published this article on September 20, 2026. Small Craft Advisor by Josh Colvinis Loose Cannon’s bestest Substack friend, having sent more readers our way than any other single source.
By JOSHUA WHEELER
A professor of mine in college would say that there wasn’t music that sucked, only music we didn’t like. With that, I present a list of my top sailor songs. I would be amazed if anyone had the same list as I. Equally so, if anyone liked every song. I don’t present myself as an authority or this as a definitive list. Rather, I’ve decided to take a risk and share my personal list to inspire the reader to wonder about theirs.
My sailor-song list stems mostly from my younger years, long before boats were even on my RADAR, therefore, I came to realize while debating this list (with myself), boat bias wasn’t why I liked most of these songs. It was because they were catchy, popular, and accessible to an audience beyond sailors. They play literally or metaphorically on a long-standing historical and communal nautical mystique and psyche that even a landlubber with little boating experience could recognize and appreciate.
I consider these sailor songs, not sailing songs. They have some personal meaning or experience tied to them. Since my relationship to music was more prominent earlier in life, my list centers on that era and is genre-specific, which coincided with my rock-and-roll lifestyle.
Without further ado:
1. The Wreck of the Edmond Fitzgerald (Gordon Lightfoot): A haunting dirge accompanying highly descriptive verse of a heart-wrenching event.
When suppertime came, the old cook came on deck sayin’“Fellas, it’s too rough to feed ya”At 7 p.m., a main hatchway caved in, he said“Fellas, it’s been good to know ya”
Southern Cross (Crosby, Stills, and Nash): Yacht rock? Absolutely. This song very much came to mind when I saw the constellation on my way to the South Seas on Sampaguita, a Pacific Seacraft Flicka 20. “Nineteen feet of waterline, nicely making way.”
Home at Last (Steely Dan): At the time, the Odyssey reference (“I remain tied to the mast.”) was lost on me, but the imagery wasn’t. For a young, budding drummer of the 80s, this track demonstrates the legendary Purdie Shuffle by drummer Bernard Purdie. Smooth.
Brandy (You’re a Fine Girl) (Looking Glass): Descriptive harbor bar imagery, sailor mystique, beauty and double-meaning to highlight one’s yearning for something one can’t (or shouldn’t) have.
Beyond the Sea (Bobby Darin) The driving, prevalent drum track of Don Lamond is legendary and has stood the test of time. The two bombastic drum fills setting up the ensemble sections are textbook examples for a young drummer to “make the band want to play!”
Sail On (Commodores): For one, the group’s name. It is a sappy song to start, but when it finally kicks into the bridge, it releases the tension like lines from the dock. “Good times never felt so good.” And what about those bongo rolls??!
(Photo by Joshua Wheeler)
Sail Away (David Gray): More sap, more metaphor, more mystique. This crooner captures a vibe of desire and yearning accessible to everyone. Keep It simple, stupid. No rocket or boat science, just very catchy.
Sailor’s Tale (King Crimson): What? Who? Why? An instrumental off the album, Islands, this band redefined what a rock band could be to me as a young musician.
I’m On a Boat (The Lonely Island): Let’s not take ourselves too seriously. This song is hilarious on many different fronts if you let it be. Poking fun at classes, stereotypes, race, language, and perceptions. I suppose you either love it or you hate it. (You might pass on listening to this if you are sensitive to salty language.)
Rime of the Ancient Mariner (Iron Maiden): A bold and ambitious endeavor by an influential 80’s metal band, celebrating the prose of Samuel Taylor Coleridge. The classic Maiden gallop, Bruce Dickinson’s operatic-esque vocals of Cook and the Nelson-era inspired lyrics, remind us that the Age of Sail was not so romantic.
The Ballad of Gilligan’s Isle (Sherwood Schwartz and George Wyle): I watched reruns of this show while eating after-school snacks before I had ever been on a boat or an island.
The Irish Rover (Traditional): This is as close to an old-timey sea shanty as I get.
Into the Mystic (Van Morrison): A crooner that somehow gets away with inserting five synth fog horns in one song. (The fifth is on the final note.)
Tahitian Moon (Porno for Pyros): Sailing and boating themes were rare in 90s alternative rock.
Cool Change (Little River Band): This direct message requires no imagination. If you know, you know.
Firefly Main Title (Sonny Rhodes): For those who can imagine what sailing could mean in a far distant future.
Boats and music are very personal things. Remember, keep your listening prudent and safe, and turn it up.
Is that Sailor rock? “Turn it up!”
Loose Cannon Adds
Privateer (Mark Knoffler): This upbeat folk-rock ditty about an late 18th century British privateer, whose ship “is small but she can sting,” captures the sense of freedom and adventure that come with being young and standing on the deck of your own boat as she thunders over the ocean.
If I Had a Boat (Lyle Lovett): This whimsical country-folk number, in which a cowboy dreams of going to sea with his pony, is about escaping from the strictures of adult life. It contains the great lines:
The mystery masked man was smart.
He got himself a Tonto
’Cause Tonto did the dirty work for free.
But Tonto he was smarter
And one day said, “Kemo Sabe,
Well, kiss my ass. I bought a boat.
I’m going out to sea.
LOOSE CANNON covers hard news, technical issues and nautical history. Every so often he tries to be funny. Subscribe for free to support the work. If you’ve been reading for a while—and you like it—consider upgrading to paid.
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