Ultimate Sailing Songs for Inspiration and Life on the Water
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What’s being on a sailboat without the best sailing songs to listen to while underway? When the sails are up, and you’ve got 10 knots on the beam, here are a few favorites that will make you never want the day to end.
Whether you’re daydreaming about sailing adventures and need a little inspiration or planning the perfect sailing playlist for a yacht charter in the Caribbean – this list of sailing music is for you!
Here are some of the best songs about sailing or being on a boat that you can add to your playlist. We also threw in a few songs that use sailing metaphors to represent different journeys or relationships in life.
Songs About Sailing Away
1. “Orinoco Flow (Sail Away)” — Enya
Album: Watermark
Release Year: 1988
This late 80s song by Enya is indeed a catchy tune. It sticks in my head every time we raise the sails. Enya’s airy voice gives this song a whimsical quality, which really fits well with the lyrics.
Listen to Orinoco Flow
Orinoco Flow Lyrics
Let me sail, let me sail
Let the Orinoco flow
Let me reach, let me beach
On the shores of Tripoli
Let me sail, let me sail
Let me crash upon your shore
Let me reach, let me beach
Far beyond the Yellow Sea
Sail away, sail away, sail away (x4)
From Bissau to Palau – in the shade of Avalon
From Fiji to Tiree and the Isles of Ebony
From Peru to Cebu hear the power of Babylon
From Bali to Cali – far beneath the Coral Sea
Turn it up, Turn it up, Turn it up, up, Adieu, Ohhhh (x3)
Sail away, sail away, sail away (x4)
From the North to the South
Ebudae into Khartoum
From the deep sea of Clouds
To the island of the moon
Carry me on the waves
To the lands I’ve never been
Carry me on the waves
To the lands I’ve never seen
We can sail, we can sail
With the orinoco flow
We can sail, we can sail…(Sail away, Sail away, Sail away)
We can steer, we can near
With Rob Dickins at the wheel
We can sigh, say goodbye
Ross and his dependency
We can sail, we can sail…(Sail away, Sail away, Sail away)
2. “Come Sail Away” — Styx
Album: The Grand Illusion
Release Year: 1977
Listen to Come Sail Away
Come Sail Away Lyrics
I’m sailing away, set an open course for the virgin sea
Cause I’ve got to be free, free to face the life that’s ahead of me
On board, I’m the captain, so climb aboard
We’ll search for tomorrow on every shore
And I’ll try, oh Lord, I’ll try to carry on
I look to the sea, reflections in the waves spark my memory
Some happy, some sad
I think of childhood friends and the dreams we had
We lived happily forever, so the story goes
But somehow we missed out on that pot of gold
But we’ll try best that we can to carry on
A gathering of angels appeared above my head
They sang to me this song of hope, and this is what they said
They said come sail away, come sail away
Come sail away with me now
Come sail away, come sail away
Come sail away with me
Come sail away, come sail away
Come sail away with me now
Come sail away, come sail away
Come sail away with me
I thought that they were angels, but to my surprise
We climbed aboard their starship, we headed for the skies
Singing come sail away, come sail away
Come sail away with me now
(x3)
Come sail away, come sail away
Come sail away with me
Come sail away, come sail away (x2)
3. “Wooden Ships” — Crosby, Stills & Nash
Album: Crosby, Stills & Nash
Release Year: 1969
Listen to Wooden Ships
Wooden Ships Lyrics
[Stills:] If you smile at me I will understand
‘Cause that is something
Everybody everywhere does in the same language
[Crosby:] I can see by your coat, my friend you’re from the other side
There’s just one thing I got to know
Can you tell me please who won?
[Stills:] Say can I have some of your purple berries?
[Crosby:] Yes, I’ve been eating them
For six or seven weeks now haven’t got sick once
[Stills:] Probably keep us both alive
Wooden ships on the water very free and easy
Easy, you know the way it’s supposed to be
Silver people on the shoreline let us be
Talkin’ ’bout very free and easy
Horror grips us as we watch you die
All we can do is echo your anguished cries
Stare as all human feelings die
We are leaving, you don’t need us
Aaaah …
Go take your sister then by the hand
Lead her away from this foreign land
Far away where we might laugh again
We are leaving, you don’t need us
And it’s a fair wind
Blowin’ warm out of the south over my shoulder
Guess I’ll set a course and go
4. “Knee Deep” — Zac Brown Band feat. Jimmy Buffet
Album: You Get What You Give
Release Year: 2010
This song is actually about trying to get over someone after a break-up. However, the laid-back, easy listening vibe of the Zac Brown Band makes you want to grab a chair, a beer, and relax by the ocean.
Listen to Knee Deep
Knee Deep Lyrics
Gonna put the world away for a minute
Pretend I don’t live in it
Sunshine gonna wash my blues away
Had sweet love but I lost it
She got too close so I fought her
Now I’m lost in the world trying to find me a better way
Wishing I was knee-deep in the water somewhere
Got the blue sky breeze and it don’t seem fair
Only worry in the world is the tide gonna reach my chair
Sunrise there’s a fire in the sky
Never been so happy
Never felt so high
And I think I might have found me my own kind of paradise
Wrote a note said “Be back in a minute”
Bought a boat and I sailed off in it
Don’t think anybody’s gonna miss me anyway
Mind on a permanent vacation
The ocean is my only medication
Wishing my condition ain’t ever gonna go away
‘Cause now I’m knee-deep in the water somewhere
Got the blue sky breeze blowing wind through my hair
Only worry in the world is the tide gonna reach my chair
Sunrise there’s a fire in the sky
Never been so happy
Never felt so high
And I think I might have found me my own kind of paradise
This champagne shore washing over me
It’s a sweet sweet life living by the salty sea
One day you could be as lost as me
Change your geography
Maybe you might be
Knee-deep in the water somewhere
Got the blue sky breeze blowing wind through my hair
Only worry in the world is the tide gonna reach my chair
Sunrise there’s a fire in the sky
Never been so happy
Never felt so high
And I think I might have found me my own kind of paradise
Come on in the water’s nice
Find yourself a little slice
Grab a backpack and lawn chair
You never know until you try
When you lose yourself
You find the key to paradise
5. “How Far I’ll Go” — Auliʻi Cravalho
Album: Moana Soundtrack
Release Year: 2016
Yes, this song is from a Disney movie, and we couldn’t possibly leave it off the list. It is the full embodiment of what it’s like to be drawn to the water. The lyrics “see the line where the sky meets the sea, it calls me” will forever ring true to your sailing spirit!
Listen to How Far I’ll Go
How Far I’ll Go Lyrics
I’ve been staring at the edge of the water
Long as I can remember, never really knowing why
I wish I could be the perfect daughter
But I come back to the water, no matter how hard I try
Every turn I take, every trail I track
Every path I make, every road leads back
To the place I know where I cannot go
Where I long to be
See the line where the sky meets the sea
It calls me
And no one knows, how far it goes
If the wind in my sail on the sea stays behind me
One day I’ll know
If I go there’s just no telling how far I’ll go
I know everybody on this island seems so happy, on this island
Everything is by design
I know everybody on this island has a role, on this island
So maybe I can roll with mine
I can lead with pride, I can make us strong
I’ll be satisfied if I play along
But the voice inside sings a different song
What is wrong with me?
See the light as it shines on the sea
It’s blinding
But no one knows, how deep it goes
And it seems like it’s calling out to me, so come find me
And let me know
What’s beyond that line, will I cross that line?
See the line where the sky meets the sea
It calls me
And no one knows, how far it goes
If the wind in my sail on the sea stays behind me
One day I’ll know
How far I’ll go
6. “Sailing” — Christopher Cross
Album: Christopher Cross
Release Year: 1979
This 80’s soft rock classic reminds us of how sailing can be the ultimate freedom — a song about sailing away from your problems and worries of the world. The dreamy melody and vocals in this song make it one of my personal favorites!
Listen to Sailing
Sailing Lyrics
Well, it’s not far down to paradise, at least it’s not for me
And if the wind is right you can sail away and find tranquility
Oh, the canvas can do miracles, just you wait and see
Believe me
It’s not far to never-never land, no reason to pretend
And if the wind is right you can find the joy of innocence again
Oh, the canvas can do miracles, just you wait and see
Believe me
Sailing takes me away to where I’ve always heard it could be
Just a dream and the wind to carry me
And soon I will be free
Fantasy, it gets the best of me
When I’m sailing
All caught up in the reverie, every word is a symphony
Won’t you believe me?
Sailing takes me away to where I’ve always heard it could be
Just a dream and the wind to carry me
And soon I will be free
Well it’s not far back to sanity, at least it’s not for me
And if the wind is right you can sail away and find serenity
Oh, the canvas can do miracles, just you wait and see
Really, believe me
Sailing takes me away to where I’ve always heard it could be
Just a dream and the wind to carry me
And soon I will be free
7. “Somewhere in the Sun” — Kenny Chesney
Album: Be As You Are
Release Year: 2005
This Chesney hit from the ‘Be As You Are’ album is about wishing you were in the islands when you are somewhere else. Kenny Chesney even references bars in the BVIs in his lyrics. If you are sitting in an office somewhere, dreaming of sailing away, this will resonate with you.
Listen to Somewhere in the Sun
Somewhere in the Sun Lyrics
Stuck here at a Holiday Inn near Austin, Texas
Seen all the road that I want to see
God I hate the snow, they even cancelled the show
Makes me long for where I really want to be
Oh I wish I was there tonight on Jost Van Dyke
Sipping on some Foxy’s Firewater rum
Or kickin’ back with Ivan
With all my friends down in the islands
Wouldn’t take much for me to up and run
To another life somewhere in the sun
Got cold fajitas and only one channel on the TV
Andy and Barney on Nick at Nite
Seen an ad for Mexico, God I really want to go
Anywhere out of mind and out of sight
Oh I wish I was there tonight on Jost Van Dyke
Sipping on some Foxy’s Firewater rum
Or kickin’ back with Ivan
With all my friends down in the islands
Wouldn’t take much for me to up and run
To another life somewhere in the sun
Here’s a toast to you on the coast and the sailors out at sea
Drink your ales, hoist your sails
Ride the winds and think of me, ’cause
Oh I wish I was there tonight on Jost Van Dyke
Sipping on some Foxy’s Firewater rum
Or kickin’ back with Ivan
With all my friends down in the islands
Wouldn’t take much for me to up and run
To another life somewhere in the sun
Somewhere in the sun
8. “Sailing” — Rod Stewart
Album: Atlantic Crossing
Release Year: 1975
Although this isn’t my favorite Rod Stewart song, I can’t deny it a position on this list. Its soft rock vibe and repeating lyrics make it an instant sing-a-long. It is a classic sailing song through and through!
Listen to Sailing
Sailing Lyrics
I am sailing, I am sailing
Home again ‘cross the sea
I am sailing, stormy waters
To be near you, to be free
I am flying, I am flying
Like a bird ‘cross the sky
I am flying, passing high clouds
To be with you, to be free
Can you hear me, can you hear me
Through the dark night, far away
I am dying, forever trying
To be with you, who can say
Can you hear me, can you hear me
Through the dark night far away
I am dying, forever crying
To be with you, who can say
We are sailing, we are sailing
Home again ‘cross the sea
We are sailing stormy waters
To be near you, to be free
(x2)
Oh Lord, to be near you, to be free
Oh (my) Lord, to be near you, to be free
Oh Lord
9. “(Sittin’ on) The Dock of the Bay” — Otis Redding
Album: The Dock of the Bay
Release Year: 1968
This classic song has all the slow-living vibes of the cruising lifestyle. I also learned something about this tune recently. The Dock of the Bay was recorded on Dec. 7, 1967. There was a difference of opinion between Redding and the studio over releasing this song. It didn’t have the same soulful beat as Redding’s popular hits. Despite this, Redding argued it would be his first No. 1 single. On Dec. 10, Otis Redding was killed in a plane crash. When the song was released in 1968, it topped the charts at No. 1 and won two Grammy Awards.
Listen to The Dock of the Bay
The Dock of the Bay Lyrics
Sittin’ in the morning sun
I’ll be sittin’ when the evening comes
Watching the ships roll in
Then I watch them roll away again, yeah
I’m sittin’ on the dock of the bay
Watchin’ the tide roll away, ooh
I’m just sittin’ on the dock of the bay
Wastin’ time
I left my home in Georgia
Headed for the Frisco Bay
‘Cause I’ve had nothing to live for
And look like nothing’s gonna come my way
So, I’m just gon’ sit on the dock of the bay
Watchin’ the tide roll away, ooh
I’m sittin’ on the dock of the bay
Wastin’ time
Looks like nothing’s gonna change
Everything still remains the same
I can’t do what ten people tell me to do
So I guess I’ll remain the same, listen
Sittin’ here resting my bones
And this loneliness won’t leave me alone, listen
Two thousand miles I roam
Just to make this dock my home, now
I’m just gon’ sit at the dock of a bay
Watchin’ the tide roll away, ooh
Sittin’ on the dock of the bay
Wastin’ time
10. “Cool Change” — Little River Band
Album: First Under the Wire
Release Year: 1979
Listen to Cool Change
Cool Change Lyrics
If there’s one thing
In my life that’s missing
It’s the time that I spend alone
Sailing on the cool
And bright clear water
Lots of those friendly people
They’re showing me ways to go
And I never want to
Lose their inspiration
Time for a cool change
I know that it’s time for a cool change
Now that my life is so prearranged
I know that it’s time for a cool change
Well, I was born in the sign of water
And it’s there that I feel my best
The albatross and the whales
They are my brothers
It’s kind of a special feeling
When you’re out on the sea alone
Staring at the full moon like a lover
Time for a cool change
I know that it’s time for a cool change
Now that my life is so prearranged
I know that it’s time for a cool change
I’ve never been romantic
And sometimes, I don’t care
I know it may sound selfish
But let me breathe the air
Yeah, yeah
Let me breathe the air
If there’s one thing
In my life that’s missing
It’s the time that I spend alone
Sailing on the cool
And bright clear water
It’s kind of a special feeling
Out on the sea alone
Staring at the full moon
Like a lover
Time for a cool change
I know that it’s time for a cool change
Now that my life is so prearranged
I know that it’s time for a cool change
(Time for a cool change)
It’s time, it’s time
It’s time, it’s time
For a cool, cool change
(Time for a cool change)
I know it’s time for a cool change
(Time for a cool change)
Now that my life is so prearranged
Well, I know, I know
I know, I know
(Time for a cool change)
It’s time for a cool change
Yes, it is, yes, it is yes, it is
You know it’s time for a cool change
11. “Sail Away” — David Gray
Album: White Ladder
Release Year: 1999
Listen to Sail Away
Sail Away Lyrics
Sail away with me, honey
I put my heart in your hands
Sail away with me, honey, now, now, now
Sail away with me
What will be will be
I wanna hold you now, now, now
Crazy skies all wild above me now
Winter howling at my face
And everything I held so dear
Disappeared without a trace
Of all the times I’ve tasted love
Never knew quite what I had
Little darling, if you hear me now
Never needed you so bad
Spinning ’round inside my head
Sail away with me, honey
I put my heart in your hands
Sail away with me, honey, now, now, now
Sail away with me
What will be will be
I wanna hold you now, now, now
I’ve been talking drunken gibberish
Falling in and out of bars
Trying to get some explanation here
For the way some people are
How did it ever come so far?
(x2)
Sail away with me, honey
I put my heart in your hands
Sail away with me, honey, now, now, now
Sail away with me
What will be will be
I wanna hold you now, now, now
Sail away with me, honey
I put my heart in your hands
Your break me up if you pull me down
Sail away with me
What will be will be
I wanna hold you now, now, now
Sailing Songs About Life
12. “Into the Mystic” — Van Morrison
Album: Moondance
Release Year: 1970
This classic rock song about a sailor coming home has so many deeper meanings and interpretations. It’s one of those songs where the lyrics strike different meanings to different people, and that’s what makes it a great sailing jam.
Listen to Into the Mystic
Into the Mystic Lyrics
We were born before the wind
Also younger than the sun
Ere the bonnie boat was won as we sailed into the mystic
Hark, now hear the sailors cry
Smell the sea and feel the sky
Let your soul and spirit fly into the mystic
And when that fog horn blows I will be coming home
And when the fog horn blows I want to hear it
I don’t have to fear it
And I want to rock your gypsy soul
Just like way back in the days of old
And magnificently we will flow into the mystic
When that fog horn blows you know I will be coming home
And when that fog horn whistle blows I got to hear it
I don’t have to fear it
And I want to rock your gypsy soul
Just like way back in the days of old
And together we will flow into the mystic
Come on girl…
Too late to stop now…
13. “When the Ship Comes In” — Bob Dylan
Album: The Times They Are a-Changin’
Release Year: 1964
Listen to When the Ship Comes In
When the Ship Comes In Lyrics
Oh the time will come up
When the winds will stop
And the breeze will cease to be breathin’
Like the stillness in the wind
‘Fore the hurricane begins
The hour when the ship comes in
And the seas will split
And the ship will hit
And the sands on the shoreline will be shaking
Then the tide will sound
And the wind will pound
And the morning will be breaking
Oh the fishes will laugh
As they swim out of the path
And the seagulls they’ll be smiling
And the rocks on the sand
Will proudly stand
The hour that the ship comes in
And the words that are used
For to get the ship confused
Will not be understood as they’re spoken
For the chains of the sea
Will have busted in the night
And will be buried at the bottom of the ocean
A song will lift
As the mainsail shifts
And the boat drifts on to the shoreline
And the sun will respect
Every face on the deck
The hour that the ship comes in
Then the sands will roll
Out a carpet of gold
For your weary toes to be a-touchin’
And the ship’s wise men
Will remind you once again
That the whole wide world is watchin’
Oh the foes will rise
With the sleep in their eyes
And they’ll jerk from their beds and think they’re dreamin’
But they’ll pinch themselves and squeal
And know that it’s for real
The hour that the ship comes in
Then they’ll raise their hands
Sayin’ we’ll meet all your demands
But we’ll shout from the bow your days are numbered
And like Pharaoh’s tribe
They’ll be drownded in the tide
And like Goliath, they’ll be conquered
14. “The River” — Garth Brooks
Album: Ropin’ the Wind
Release Year: 1991
This country ballad uses the metaphor of a river and a vessel to illustrate what it’s like to chase what you want and never give up on your dreams. So many sailors can relate to this mentality, so it had to make this list!
Listen to The River
The River Lyrics
You know a dream is like a river
Ever changin’ as it flows
And a dreamer’s just a vessel
That must follow where it goes
Trying to learn from what’s behind you
And never knowing what’s in store
Makes each day a constant battle
Just to stay between the shores…and
I will sail my vessel
‘Til the river runs dry
Like a bird upon the wind
These waters are my sky
I’ll never reach my destination
If I never try
So I will sail my vessel
‘Til the river runs dry
Too many times we stand aside
And let the waters slip away
‘Til what we put off ’til tomorrow
Has now become today
So don’t you sit upon the shoreline
And say you’re satisfied
Choose to chance the rapids
And dare to dance the tide…yes
I will sail my vessel
‘Til the river runs dry
Like a bird upon the wind
These waters are my sky
I’ll never reach my destination
If I never try
So I will sail my vessel
‘Til the river runs dry
There’s bound to be rough waters
And I know I’ll take some falls
But with the good Lord as my captain
I can make it through them all…yes
I will sail my vessel
‘Til the river runs dry
Like a bird upon the wind
These waters are my sky
I’ll never reach my destination
If I never try
So I will sail my vessel
‘Til the river runs dry
Yes, I will sail my vessel
‘Til the river runs dry
‘Til the river runs dry
Songs About Sailors
15. “Treat Her Like a Lady” — Jimmy Buffett
Album: Volcano
Release Year: 1979
Ok, confession time. I wouldn’t say I like Jimmy Buffett that much (don’t throw stones, please). But, when we bought our boat, Jimmy Buffett’s Volcano album was in the CD player. Since it was the only CD on board, we would often play it when we didn’t want to hook up the Bluetooth. From that album came this song about a sailor’s love for the ocean. It’s a slower tempo than most of his more popular songs, and I think it’s a nice change of pace.
Listen to Treat Her Like a Lady
Treat Her Like a Lady Lyrics
Some of us sailors call her home
She’s big and she’s strong and she’s mighty
Some of us sailors call her our own
Guess that’s the reason why I treat her like a lady
Just treat her like a lady
Now I don’t like the sound of the ground movin’ ’round
Or winds spinnin’ out of control
California earthquakes only seem to make a’ me
Shake, rattle, and roll
I’ve been too long on the mainland
Hotels, rental cars, and phones
Time to cast ’em aside, catch the very next tide
And go back where I belong
Some of us sailors call her home
She’s big and she’s strong and she’s mighty
Some of us sailors call her our own
Guess that’s the reason why I treat her like a lady
Treat her like a lady
Now great whales travel the rhumb lines
Dodging those deadly harpoons
Spawning their young as their ancestors done
In the depths of her hidden lagoons
There’re times I find myself with them
And times I feel as they do
We’re on a similar course, it’s just a different source
But I’m in danger of extinction too
Some of us sailors call her home
She’s big and she’s strong and she’s mighty
Some of us sailors call her our own
Guess that’s the reason why I treat her like a lady
Treat her like a lady (x3)
And miss her when I’m gone
(Lady, lady) treat her like a lady
(Lady, lady) treat her like a lady
(Lady, lady) got to treat her like a lady
(Lady, lady) treat her like a lady
Lady, lady (x3)
16. “Lost Sailor” — Grateful Dead
Album: Go to Heaven
Release Year: 1980
Listen to Lost Sailor
Lost Sailor Lyrics
Compass card is spinning
Helm is swingin’ to and fro
Ooh, where’s the dog star?
Ooh, where’s the moon?
You’re a lost sailor
You’ve been too long at sea
Some days the gales are howling
Some days the sea is still as glass
Ooh, reef the main sail
Ooh, lash the mast
You’re a lost sailor
You’ve been too long at sea
Now the shore lights beckon
Yeah there’s a price for being free
Yeah the sea birds cry
There’s a ghost wind blowin’
It’s calling you, to that misty swirling sea
‘Til the chains of your dreams are broken
No place in this world you can be
You’re a lost sailor
You’ve been way too long at sea
Now the shore lights beckon
Yeah there’s a price for being free
Drifting yeah drifting
Yeah drifting and dreaming
‘Cause there’s a place you’ve never been
Maybe a place you’ve never seen
You can hear her calling on the wind
Go on and drift your life away
Yeah just drifting and dreaming
Maybe drift your life away
Drifting and dreaming
Yes I’m going on a dream
Maybe going on a dream (x4)
17. “Sail On, Sailor” — The Beach Boys
Album: Holland
Release Year: 1973
The Beach Boys have a ton of music about sailing. This one is particularly excellent due to the message of perseverance on the ocean and in life. Sail on, sail on, sailor!
Listen to Sail On, Sailor
Sail On, Sailor Lyrics
I sailed an ocean, unsettled ocean
Through restful waters and deep commotion
Often frightened, unenlightened
Sail on, sail on, sailor
I wrest the waters, fight Neptune’s borders
Sail through the sorrows of life’s marauders
Unrepenting, often empty
Sail on, sail on, sailor
Caught like a sewer rat, alone, but I sail
Bought like a crust of bread, but oh, do I wail
Seldom stumble, never crumble
Try to tumble, life’s a rumble
Feel the stinging I’ve been given
Never-ending, unrelenting
Heartbreak searing, always fearing
Never clearing, persevering
Sail on, sail on, sailor
I work the seaways, the gale-swept seaways
Past shipwrecked daughters of wicked waters
Uninspired, drenched, and tired
Wail on, wail on, sailor
Always needing, even bleeding
Never feeding all my feelings
Damn the thunder, must I blunder
There’s no wonder all I’m under
Stop the crying and the lying
And the sighing and my dying
Sail on, sail on, sailor
Sail on, sail on, sailor
Sail on, sail on, sailor
Sail on, sail on, sailor
Sail on, sail on, sailor
Sail on, sail on, sailor
Sail on, sail on, sailor
18. “A Pirate Looks at Forty” — Jimmy Buffett
Album: A1A
Release Year: 1974
Listen to A Pirate Looks at Forty
A Pirate Looks at Forty Lyrics
Mother, mother ocean, I have heard you call
Wanted to sail upon your waters since I was three feet tall
You’ve seen it all,you’ve seen it all
Watched the men who rode you switch from sails to steam
And in your belly you hold the treasures few have ever seen
Most of them dream, most of them dream
Yes I am a pirate, two hundred years too late
The cannons don’t thunder, there’s nothing to plunder
I’m an over-forty victim of fate
Arriving too late, arriving too late
I’ve done a bit of smuggling, I’ve run my share of grass
I made enough money to buy Miami, but I pissed it away so fast
Never meant to last, never meant to last
And I have been drunk now for over two weeks
I passed out and I rallied and I sprung a few leaks
But I got stop wishing, got to go fishing, down to rock bottom again
Just a few friends, just a few friends
I go for younger women, lived with several a while
Though I ran them away, they’d come back one day
Still could manage to smile
Just takes a while, just takes a while
Mother, mother ocean, after all the years I’ve found
My occupational hazard being my occupation’s just not around
I feel like I’ve drowned, gonna head uptown
I feel like I’ve drowned, gonna head uptown
19. “Soul of a Sailor” — Kenny Chesney
Album: Be As You Are
Release Year: 2005
The ‘Caribbean Cowboy’ has his share of sailing songs. This one is surprisingly perfect when it comes to the heart of a sailor. “When the wind fills my sail, riding on a lifelong swell, let my heart take me where it wants to go – that’s the soul of a sailor.”
Listen to Soul of a Sailor
Soul of a Sailor Lyrics
He walked in with a salty sway
Lookin’ like Blackbeard in his day
A brother in arms just like me
I was born a son of the sea
I can’t be still, I can’t be tied
The only time I feel alive is
When the wind fills my sail
Riding on a lifelong swell
Let my heart take me where it wants to go
That’s the soul of a sailor, the soul of a sailor
He slid a stool and a beer to me
Said, you know, we’re both a dying breed
Here’s to love lost and newfound friends
And living out life in the boat we’re in
I can’t be still, I can’t be tied
The only time I feel alive is
When the wind fills my sail
Riding on a lifelong swell
Let my heart take me where it wants to go
That’s the soul of a sailor, the soul of a sailor
Let my heart take me where it wants to go
That’s the soul of a sailor, the soul of a sailor
20. “Single Handed Sailor” — Dire Straits
Album: Communiqué
Release Year: 1979
Listen to Single Handed Sailor
Single Handed Sailor Lyrics
Two in the morning, dry-dock town
The rivers rolls away in the night
Little gypsy moth she’s all tied down
She quiver in the wind and the light
Yeah and a sailing ship just held down in chains
From the lazy days of sail
She’s just lying there in silent pain
He lean on the turist rail
A mother and her baby and the college of war
In the concrete graves
You never wanna fight against the river law
Nobody rules the waves
Yeah and on a night when the lazy wind is a-wailing
Around the Cutty Sark
Single handed sailor goes sailing
Sailing away in the dark
He’s upon the bridge on the self same night
The mariner of dry dock land
Two in the morning, but there is one green light
And a man on the barge of sand
She’s gonna slip away below him
Away from the things he’s done
But he just shouts “Hey man, what do you call this thing?”
He could have said “Pride of London”
On a night when the lazy wind is a-wailing
Around the Cutty Sark
Yeah the single handed sailor goes sailing
Sailing away in the dark
21. “Drunken Sailor” — Irish Rovers
Album: Drunken Sailor
Release Year: 2012
Listen to Drunken Sailor
Drunken Sailor Lyrics
What will we do with a drunken sailor? (x3)
Early in the morning
Weigh-hey and up she rises (x3)
Early in the morning
Shave his belly with a rusty razor (x3)
Early in the morning
Weigh-hey and up she rises (x3)
Early in the morning
Put him in a long boat ’til he’s sober (x3)
Early in the morning
Weigh-hey and up she rises (x3)
Early in the morning
Stick him in the scupper with a hosepipe on him (x3)
Early in the morning
Weigh-hey and up she rises (x3)
Early in the morning
Put him in the bed with the captain’s daughter (x3)
Early in the morning
Weigh-hey and up she rises (x3)
Early in the morning
That’s what we do with a drunken sailor (x3)
Early in the morning
(x2)
Weigh-hey and up she rises (x3)
Early in the morning
22. “Son of a Son of a Sailor” — Jimmy Buffett
Album: Son of a Son of a Sailor
Release Year: 1978
Listen to Son of a Son of a Sailor
Son of a Son of a Sailor Lyrics
As the son of a son of a sailor
I went out on the sea for adventure
Expanding the view of the captain and crew
Like a man just released from indenture
As a dreamer of dreams and a travelin’ man
I have chalked up many a mile
Read dozens of books about heroes and crooks
And I learned much from both of their styles
Son of a son, son of a son
Son of a son of a sailor
Son of a gun, load the last ton
One step ahead of the jailer
Now away in the near future
Southeast of disorder
You can shake the hand of the mango man
As he greets you at the border
And the lady, she hails from Trinidad
Island of the spices
Salt for your meat and cinnamon sweet
And the rum is for all your good vices
Haul the sheet in as we ride on the wind
That our forefathers harnessed before us
Hear the bells ring as the tight rigging sings
It’s a son of a gun of a chorus
Where it all ends I can’t fathom my friends
If I knew I might toss out my anchor
So I cruise along, always searchin’ for songs
Not a lawyer, a thief, or a banker
But a son of a son, son of a son
Son of a son of a sailor
Son of a gun, load the last ton
One step ahead of the jailer
I’m just a son of a son, son of a son
Son of a son of a sailor
The sea’s in my veins, my tradition remains
I’m just glad I don’t live in a trailer
Sailing Songs About Love
23. “Brandy (You’re a Fine Girl)” — The Looking Glass
Album: Looking Glass
Release Year: 1972
This is one of the best sailing songs of the 70s and truly exemplifies the sailor lifestyle. It’s about a girl in love with a sailor whom she will never be able to steal from the sea. The line “But my life, my love, and my lady is the sea” is something anyone who loves the water can relate to.
Listen to Brandy
Brandy Lyrics
There’s a port on a western bay
And it serves a hundred ships a day
Lonely sailors pass the time away
And talk about their homes
And there’s a girl in this harbor town
And she works layin’ whiskey down
They say, “Brandy, fetch another round”
She serves them whiskey and wine
The sailors say, “Brandy, you’re a fine girl” (you’re a fine girl)
“What a good wife you would be” (such a fine girl)
“Yeah, your eyes could steal a sailor from the sea”
Brandy wears a braided chain
Made of finest silver from the North of Spain
A locket that bears the name
Of a man that Brandy loved
He came on a summer’s day
Bringin’ gifts from far away
But he made it clear he couldn’t stay
No harbor was his home
The sailor said, “Brandy, you’re a fine girl” (you’re a fine girl)
“What a good wife you would be” (such a fine girl)
“But my life, my love, and my lady is the sea”
Yeah, Brandy used to watch his eyes
When he told his sailor’s story
She could feel the ocean fall and rise
She saw its ragin’ glory
But he had always told the truth, Lord, he was an honest man
And Brandy does her best to understand
At night, when the bars close down
Brandy walks through a silent town
And loves a man who’s not around
She still can hear him say
She hears him say, “Brandy, you’re a fine girl” (you’re a fine girl)
“What a good wife you would be” (such a fine girl)
“But my life, my love and my lady is the sea”
“Brandy, you’re a fine girl” (you’re a fine girl)
“What a good wife you would be” (such a fine girl)
“But my life, my love, and my lady is the sea”
24. “Southern Cross” — Crosby, Stills, & Nash
Album: Daylight Again
Release Year: 1982
This 80s song about a failed relationship got renewed life when Jimmy Buffett started covering it at his live shows in the 90s. All the sailing terms and references in this one definitely make it a sailing song classic.
Listen to Southern Cross
Southern Cross Lyrics
Got out of town on a boat goin’ to Southern islands
Sailing a reach before a followin’ sea
She was makin’ for the trades on the outside
And the downhill run to Papeete
Off the wind on this heading lie the Marquesas
We got eighty feet of the waterline nicely making way
In a noisy bar in Avalon I tried to call you
But on a midnight watch I realized why twice you ran away
Think about
Think about how many times I have fallen
Spirits are using me larger voices callin’
What Heaven brought you and me cannot be forgotten
(Been around the world) I have been around the world
(Lookin’) Lookin’ for that woman girl
(Who knows she knows) Who knows love can endure
And you know it will
Yes
When you see the Southern Cross for the first time
You understand now why you came this way
‘Cause the truth you might be runnin’ from is so small
But it’s as big as the promise, the promise of a comin’ day
So I’m sailing for tomorrow my dreams are a dyin’
And my love is an anchor tied to you tied with a silver chain
I have my ship and all her flags are a’ flyin’
She is all that I have left and music is her name
Think about
Think about how many times I have fallen
Spirits are using me larger voices callin’
What Heaven brought you and me cannot be forgotten
(I’ve been around the world) I have been around the world
(Lookin’) Lookin’ for that woman girl
Who knows love can endure
And you know it will, and you know it will
Yes
So we cheated, and we lied, and we tested
And we never failed to fail, it was the easiest thing to do
You will survive being bested
Somebody fine will come along, make me forget about loving you
At the Southern Cross
25. “Islands in the Stream” — Dolly Parton & Kenny Rogers
Album: Eyes That See in the Dark
Release Year: 1983
The Bee Gee’s Barry Gibb wrote this iconic duet. It’s got all the feels of a sailing love song and has definite karaoke potential. Or, as I prefer, just singing to the waves while at the helm. Either way, this is a must-have for your sailing songs playlist.
Listen to Islands in the Stream
Islands in the Stream Lyrics
Baby, when I met you
There was peace unknown
I set out to get you
With a fine tooth comb
I was soft inside
There was something going on
You do something to me
That I can’t explain
Hold me closer and I feel no pain
Every beat of my heart
We got something going on
Tender love is blind
It requires a dedication
All this love we feel
Needs no conversation
We ride it together, ah-ha
Making love with each other, ah-ha
Islands in the stream
That is what we are
No one in between
How can we be wrong
Sail away with me
To another world
And we rely on each other, ah-ha
From one lover to another, ah-ha
I can’t live without you
If the love was gone
Everything is nothing
If you got no one
And you just walk in the night
Slowly losing sight of the real thing
But that won’t happen to us
And we got no doubt
Too deep in love and we got no way out
And the message is clear
This could be the year for the real thing
No more will you cry
Baby, I will hurt you never
We start and end as one
In love forever
We can ride it together, ah-ha
Making love with each other, ah-ha
Islands in the stream
That is what we are
No one in between
How can we be wrong
Sail away with me
To another world
And we rely on each other, ah-ha
From one lover to another, ah-ha
Sail away
Ooooh, come sail away with me
(x2)
Islands in the stream
That is what we are
No one in between
How can we be wrong
Sail away with me
To another world
And we rely on each other, ah-ha
From one lover to another, ah-ha
Islands in the stream
That is what we are
No one in between
Where to Find More Songs for Sailors
There have been many great sailing songs, both new and old, over the years. Not to mention all the incredible songs about freedom, adventure, and pushing your boundaries.
And for more inspiration, check out the below Spotify playlist of 500 Sailing Songs for Sailors.
READ NEXT
- If you liked this post, you might also like 50 of the Best Sailing Quotes to Live By.
- Or get visually inspired with our list of 13 of the Best Sailing Movies and Documentaries.
Want to find more sailing inspiration?
Check out our lists of sailing movies, quotes, books, and more that inspire this lifestyle.
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Love this Morgan! So fun. These would be great for summer in general too ☺️🤘🏼
Definitely! This could totally be inspo for a summer playlist 😄
What a fun list Morgan!
Thanks! I love a good playlist out on the water 🙂
What a fun list of songs!! Music will always get me in the spirit!😍
Thanks, Jodie! I’m the same. Whatever I’m doing it’s better with good tunes 🙂
Okay I love the idea of pairing music to my adventures!! It builds so many memories!!
Absolutely! Good beats make everything better.