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The 10 Best Songs About Sailing and the Sea

The Schooner Pride – Charleston, SC

There’s something about sailing that can make one feel comfortable with everything happening in their lives and in the world, at least for a little while. Where there is peace, though, there is also the mighty strength of the sea that can bite back at you when you least expect it, throwing your boat and your life together into chaos.

Many songwriters have touched upon the subject of sailing and the sea, both from the easygoing, fun-loving side, and from the dark, deceptive underbelly.

Some of this music, namely the stuff from the fun-loving easygoing side of things, has managed to become corny over the years due to being overplayed at beachside resorts everywhere.

We’ve done our best to avoid those songs with this list, but we can’t promise that we stuck to our self-imposed rules very strictly. That’s not how sailing works, remember?

Find below our list of the 10 best songs about sailing and the sea.

10. Jack Johnson, Dave Matthews & Tim Reynolds – “A Pirate Looks At Forty” (Jimmy Buffet Cover)

I was hesitant to include any Jimmy Buffett songs on this list, because I’m honestly pretty tired of hearing Jimmy Buffet songs on boats these days, but I couldn’t bring myself to leave this one off.

“A Pirate Looks At Forty” is one of a few Jimmy Buffett songs that hasn’t been totally spoiled by my day job on the water, and the live rendition done by Jack Johnson & Dave Matthews from the Kokua Festival album is in my opinion even better than the original. Jack & Dave make for a nice combination, and Tim Reynolds on guitar really solidifies this choice.

See a live video of the performance below.

9. Anders Osborne – “Cape Cod”

Easily the least well-known song on this list is “Cape Cod” by Anders Osborne. Released on his 2016 album Spacedust & Ocean Views, “Cape Cod” is a mellow, atmospheric song that feels like drifting about on a boat or on the beach.

The lyrics paint a picture of Cape Cod on a lazy summer afternoon, while Anders spins a gentle breeze with his guitar, backed by sweet and delicate violins. The entire album is filled with this kind of stuff, but “Cape Cod” is prime when it comes to sailing music and songs that invoke the energy of the ocean.

Another great song on Spacedust & Ocean Views that you should check out is “Life Don’t Last That Long”.

Listen to “Cape Cod” by Anders Osborne below.

8. Styx – “Come Sail Away”

I know I said I was going to do my best to avoid the corny sailing songs on this list, but “Come Sail Away” by Styx holds merit, despite being overplayed and gimmickized at this point.

The vocals in the intro, while over-the-top and borderline cringeworthy do have a certain epic feel to them that will make you feel like you’re embarking on a very important and memorable journey at sea, if you let it. Then things get wild and the song takes a hard left turn into heavy rock n roll, as if the rollicking ocean has taken hold of your ship.

Try to forget about your parents’ high school dance for a minute and enjoy this song as if it’s the first time you’ve ever heard it.

Watch the video for “Come Sail Away” by Styx below.

7. Grateful Dead – “Lost Sailor”

Naturally the Grateful Dead have made their way onto my website again, this time on a list of sailing music. “Lost Sailor” comes from the Dead’s 1980 album Go To Heaven, which was not well-received at the time of its release but has since held its own as one of their stronger studio records.

As we know, the Grateful Dead are not exactly known for their studio recordings, but the songs certainly hold their own. This is just one of those bands that captures the energy much better in the live environment.

As the title suggests, “Lost Sailor” tells the story of a sailor lost at sea, experiencing the horrors of the ocean and finding himself at its mercy. It’s certainly not one of your happy-go-lucky sunshine in the afternoon sailing songs, but rather a song about the sea and what its dark underbelly can do to you.

Since I personally recommend a live take on “Lost Sailor”, and especially with its paired with “Saint of Circumstance”, I’ve included streams of both the Go To Heaven studio cut and what Headyversion considers the best-ever live version of “Lost Sailor” > “Saint of Circumstance”, the one from 10/10/82, below.

I can attest to the live version being fantastic, and you might just find yourself taking your very own journey through the cosmic seas if you do happen to indulge.

6. Tom Petty – “Wildflowers”

The title and opening track off Tom Petty’s second solo studio album, 1994’s Wildflowers is a classic song that captures the peaceful energy that one might feel while sailing.

While some of the music on this list are strictly songs about the sea, “Wildflowers” is one of several that I would actually recommend you listen to while sailing, if you have the chance.

The lyrics explore moving forward and moving on, finding peace within yourself and doing what makes you feel free, which includes sailing away. “Wildflowers” is about an ending and a new beginning, and pairs nicely with the healthy escapism that sailing can become.

Listen to “Wildflowers” by Tom Petty below.

5. Van Morrison – “Into The Mystic”

“Into The Mystic” by Van Morrison is another sailing song that also happens to fit perfectly with the act of sailing. Driven by a rolling bass line that feels like a peaceful wave on the ocean, Van Morrison captures the steady forward motion that you’d have before a consistent breeze.

The chorus feels like catching a puff, with trumpets joining in to move your boat along its course. Many of Van Morrison’s songs have a certain nautical energy to them, as well, and you really can’t go wrong with a day on the water spinning Moondance.

Listen to “Into The Mystic” by Van Morrison below. Also check the live cover done by Jason Isbell & The 400 Unit from their Live At Twist & Shout 11.16.07 album here.

4. Otis Redding – “(Sittin’ On) the Dock of the Bay”

No song that I know of encapsulates a gentle afternoon by the seaside better than Otis Redding’s classic “(Sittin’ On) the Dock of the Bay”. This one will forever remind me of summers spent growing up sailing, racing around the Great South Bay with all of my now-oldest pals.

It bobs along, always referencing the beautiful day and the sights and sounds and feelings in the air, while at the same time lamenting on a situation that is outside of his control. Since there’s nothing he can do about it, there’s not much else to do other than just sit on the dock of the bay, watchin’ the tide roll away, listening to songs by the sea.

Listen to “(Sittin’ On) the Dock of the Bay” by Otis Redding below.

3. Neil Young – “Captain Kennedy”

Neil Young is no stranger to the sea, nor of writing songs about the sea. His music often referenced nautical themes, and in fact for nearly 30 years he owned the 101 foot Baltic Trader W.N. Ragland, and did much sailing with her over the years.

I heard a story from an old captain who was in the Caribbean with Neil back in the late 70s and recalls Neil playing and writing music on board at night, with the whole ship listening in delight.

It was during that time that Young recorded the formerly lost album Hitchhiker (1976), which is where the song “Captain Kennedy” was first heard. The story goes that the album was initially scrapped by the label, and “Captain Kennedy” instead made its debut on 1980’s Hawks & Doves. Hitchhiker was released in 2017 as part of Neil’s archival release project.

“Captain Kennedy” is a haunting song that was reportedly written about Neil Young’s seafaring grandfather, Captain Louis Kennedy. It chronicles the story of a mariner who runs a freighter in the islands.

Neil plays and sings in a somewhat jarring way that contributes to that uncertain “lost at sea” vibe that this song curates. None of that signature Old Black guitar sound here, but fantastic in its own right.

Listen to “Captain Kennedy” by Neil Young below.

2. Brand New – “Play Crack The Sky”

Now, I want to put a disclaimer here because I’m sure that most people reading this have never heard of Brand New or “Play Crack The Sky”.

This is an exceptionally sad, well-written song about death told through the lens of a shipwreck. It comes from Brand New’s 2003 album Deja Entendu, which is an album that has helped me through some hard times, and holds a very special place in my life.

“Play Crack The Sky” is as much about the might of the ocean as it is about the weight of sorrow, and what both can do to a person if they find themselves caught in a rough storm.

Jesse Lacey’s songwriting is poignant and poetic, and the lyrics are exceptionally touching to those of us who have a real-life connection with boats and the ocean.

“Play Crack The Sky” is one of my personal all-time favorite songs, so I may be a bit biased with my placement of it on this list, but if you’re a sailor or a mariner and you’ve ever had a broken heart, you might find that this song speaks to you on a deep level.

It’s a creative painting that explores the great force of the sea and uses it as a vehicle for coming to terms with existential dread and unavoidable death. It’s beautiful and holds its own on in the category of songs about the sea. Just don’t put it on your “Margaritaville” playlist. You might bum some people out.

Listen to “Play Crack The Sky” by Brand New below.

1. Crosby, Stills, Nash & Young – “Wooden Ships” and “Southern Cross”

No list of sailing songs would be complete without either “Wooden Ships” or “Southern Cross”, and since they’re both incredible songs, albeit very similar, I’ve decided to award them both the distinction of the best all-time sailing songs.

David Crosy, Steven Stills, Graham Nash, and Neil Young are all sailors in their own right, and when they came together to write a sailing song, I tell you, they could really do it.

“Wooden Ships” and “Southern Cross” are pretty easy to get mixed up, but they’re both damn good songs so it doesn’t really matter.

These two songs both capture the energy and freedom of sailing, and they do this in a magical and evocative way that makes you feel like you’re right there with them on the open ocean. Away from it all, with nothing to bother you and clear blue skies ahead.

Listen to “Wooden Ships” and “Southern Cross” by Crosby, Stills Nash & Young below.