26 Of The Best Songs About Sailing: Sailor Playlist

Written by Dan Farrant

Sailing captures our imagination because it evokes a sense of adventure and freedom across the vast sea. When we think of sailing, we think of carefree days when we just enjoy the moment and life in general.

Songwriters have captured this very essence of sailing into timeless songs that transport us to distant shores. Whether we are in a boat or far from the sea, these songs make us yearn to go on a voyage.

Are you in search of the perfect playlist for a sea-based adventure? We are inviting you to enjoy our list of 26 of the best songs about sailing. So stick around and have fun reading!

1. “Sail On” By The Commodores

First on our list is The Commodores‘ “Sail On.” This song beautifully encapsulates the sentiment of embarking on a voyage as it encourages listeners to sail on regardless of the circumstances.

Though this is a song with “sail” in the title, it’s not about sailing in the literal sense. The term is a metaphor for going through life despite the end of a relationship.

The lyrics represent resilience and courage as the narrator talks about sailing on to good times. “Sail On” captures the essence of navigating through the challenges that life brings.

2. “Cool Change” By Little River Band

One of the most popular singles by the Little River Band is “Cool Change.” We cannot complete our list without this track as this is every bit of a sailing song.

The lyrics find the narrator seeking comfort, inner peace, and rejuvenation through sailing. He desires to get away from the hustle and bustle of life and get out on the water for some much need alone time. It’s not selfish to want to be alone for a while, as this allows you to breathe and recharge.

Getting away from everything and enjoying a simpler existence – often associated with life at sea – is indeed a cool change.

3. “The Last Farewell” By Roger Whittaker

Here we have a romantic ballad about separation by Roger Whittaker. “The Last Farewell” follows a sailor’s final goodbye before he embarks on a journey.

This classic captures the longing, sadness, and bravery associated with life at sea. Whittaker’s soulful voice only accentuates this feeling further as the narrator is about to leave a land of sunshine for a rainy old England.

The song captures the difficulty of saying goodbye and embarking on a journey into the unknown. The narrator feels so dejected that he can only imagine being back on the island again and back in his lover’s arms.

4. “Sailing Ships” By Whitesnake

Another song that mentions “sailing” in a metaphorical way is Whitesnake‘s “Sailing Ships.” Here, sailing represents self-discovery, growth, and taking control of one’s life.

In the lyrics, we find the narrator by the shore, ready to embark on a journey to fulfill his dreams. Many challenges are about to come his way, such as an ocean deeper than he anticipates and a dark horizon due to a storm coming.

The song encourages listeners to keep sailing despite the obstacles. Follow your dreams and seize opportunities before they pass you by.

5. “Sailing” By Christopher Cross

One of the most popular songs about sailing is by Christopher Cross. “Sailing” was released in 1980 and was a critical and commercial success. It won three Grammy Awards: Record of the Year, Song of the Year, and Arrangement of the Year. It also topped the Billboard Hot 100 for a week.

Thematically, the song is about sailing and the freedom that comes with it. Sailing is used as a metaphor for one’s journey in life, where the narrator finds an escape from the hustle and bustle of everyday life.

The lyrics evoke images of peaceful sails across calm seas, creating a sense of tranquility and exploration. As Cross sings about finding his inner peace, listeners can’t help but feel inspired to embark on their own voyages – whether literally or metaphorically.

6. “Southern Cross” By Crosby, Stills & Nash

The timeless classic “Southern Cross” by Crosby, Stills & Nash uses sailing as a metaphor for self-discovery and transformation. It talks about leaving everything behind and sailing toward the Southern Cross constellation.

The song references Southern Cross, which sailors rely on to navigate their boats. But in this song, the constellation is used by the narrator to help him navigate around love.

While the song can be interpreted in many ways, it seems to explore themes of love, loss, and finding oneself in the vastness of the universe. It also explores one’s journey through emotional healing while sailing in the open seas.

7. “Orinoco Flow” By Enya

Up next is the song “Orinoco Flow” by the Irish singer-songwriter Enya. This captivating song takes you on an enchanting journey across the ocean.

The song is simple enough, with the premise of leaving everything behind and sailing to various locations around the world. The lyrics paint a picture of voyaging and experiencing the freedom of being out at sea.

The Orinoco Flow refers to two things. It is the name of the studio where the song was recorded. It also refers to the 1,400-mile river located in South America.

Enya’s mesmerizing voice, combined with the gentle rhythm, creates a sense of tranquility and wanderlust, making it the perfect addition to any sailing playlist.

8. “Come Sail Away” By Styx

Another song with “sailing” in the lyrics is “Come Sail Away” by Styx. This classic rock song is about following your dreams, although the journey forward is unknown.

The song starts off slow and melodic, with singer Dennis DeYoung crooning about dreaming of escaping to a better place. As the song progresses, it builds into an epic anthem, complete with soaring guitar solos and harmonized vocals.

Aside from escapism, the song also explores nostalgia and the pursuit of freedom. The lyrics tell the story of someone who feels trapped in his everyday life and yearns for something more. He dreams of setting sail on a ship and leaving troubles behind.

9. “Beyond The Sea” By Bobby Darin

In “Beyond the Sea” by Bobby Darin, sailing is a backdrop for the narrator’s love story. He longs to be reunited with his lover, who is far away, waiting for him “on golden sands” while watching the ships sailing away.

The song evokes yearning and anticipation as he dreams of crossing the vast ocean to get to her. It might not be now, but he knows that one day, he’ll get to her, and there’ll be no need to go sailing again.

As you can see from the lyrics, there is no distance that can separate two people who love each other. The song highlights the narrator’s determination to overcome challenges in the name of love.

10. “Red Sails In The Sunset” By The Platters

The classic ballad “Red Sails in the Sunset” by The Platters transports listeners to a serene and romantic seaside setting. Here, the narrator is anticipating the fast arrival of his lover aboard a ship with red sails.

The lyrics convey his desire to be reunited with her and show the strength of their love. At the moment, though, he is antsy as he waits for her, who has been sailing since dawn. He feels blue with anticipation, praying that the “red sails” will bring her to him safely and they can wed the following day.

Sailing and the red sails against the sunset are a vision of hope and optimism for his lover’s arrival. They also symbolize love and reunion after a journey across the seas.

11. “A Sailboat In The Moonlight” By Billie Holiday

Sailing and romance must be two of the best things on Earth. Billie Holiday‘s song “A Sailboat in the Moonlight” agrees as it captures the essence of sailing under the night sky with your love interest.

The song is full of imagery as Holiday sings about “A sailboat in the moonlight and you, Wouldn’t that be heaven, A heaven just for two.” Being together on a dreamy voyage aboard a sailboat under the moonlight is the “perfect setting” for a romantic night.

The narrator expresses her contentment with this private moment with her lover. It’s a peaceful and intimate experience away from the distractions of the world.

12. “Brandy (You’re A Fine Girl)” By Looking Glass

The American pop band Looking Glass secures a spot on our list with their 1972 single “Brandy (You’re a Fine Girl).” Written by lead guitarist Elliot Lurie, it’s about Brandy, a barmaid living in a busy port town that “serves a hundred ships a day.”

She catches the eye of sailors but cannot be tamed by their flirting because her heart is reserved for one particular sailor. Sadly, he cannot return her affection because he cannot stay in one place. His life is at sea, and it will always be the choice he chooses.

Brandy understands and can even see the truth in his words from the way he tells his sailor stories. Perhaps the most painful is hearing him say, “My lady is the sea.”

13. “Sailing Away” By Chris De Burgh

In “Sailing Away” by Chris de Burgh, the narrator watches the ships come in and dreams of exploring the world. The song explores themes of freedom and adventure through sailing.

And while ships leave the port, the narrator thinks of all the places he has not been to yet. The song depicts that sailing is one way of breaking free from the hustle and bustle of life and discovering something more, something different.

In addition, the narrator yearns for the opportunity to sail away with his partner, symbolizing a desire for shared adventures and the pursuit of their dreams.

14. “Sail Away” By David Gray

Escape, freedom, and yearning for a second chance are just some of the themes you’ll find in David Gray‘s “Sail Away.”

In this beautiful and poignant song, the narrator longs to reconcile with a loved one who has drifted away from him. Perhaps she had left him after taking her for granted, as shown by the lines, “Oh all the times I’ve tasted love, Never knew quite what I had.”

He realizes just how much she means to him and wants her back. Sailing away seems to be the perfect idea to begin healing their relationship.

15. “Into The Mystic” By Van Morrison

Up next is a timeless classic that captures the essence of sailing and the ocean’s mystique. “Into the Mystic” by Van Morrison has a serene melody and heartfelt lyrics that transport listeners to a place where they can imagine themselves sailing away on an adventurous voyage.

“Into the Mystic” is subject to different interpretations. It can be that life is a finite voyage and has an end. Or it can be understood as living in the moment.

In the lyrics, the narrator is at sea and contemplates going back to his lover. The lines “When that fog horn whistle blows… I don’t have to fear it” refers to the fact that foghorns usually signal danger. But in the song, the foghorn means he’s close to home and his lover.

16. “Anchors Aweigh” By US Navy Band

Let us not forget “Anchors Aweigh” by the US Navy Band. This patriotic song holds a special place in the heart of the Navy. It captures the spirit of naval traditions and serves as a rallying cry for sailors around the world.

The title refers to raising the anchor of a ship, symbolizing departure and embarking on new adventures at sea. It celebrates the bravery, camaraderie, and dedication of people who sail into unknown waters to defend their country’s interests.

This song continues to inspire generations with its message of courage, loyalty, and unwavering determination to navigate life’s challenges head-on – just like a sailor setting off on an epic voyage across uncharted seas.

17. “A Pirate Looks At Forty” By Jimmy Buffett

Singer-songwriter Jimmy Buffet wrote “A Pirate Looks at Forty” about Phil Clark, whom he met in the early ’70s. Clark was in his late 30s during this time and was considered a modern-day pirate. In other words, he was a smuggler, an adventurer, and even a mercenary.

Buffett wrote the song based on their conversations. The title came from the fact that Clark was nearing 40 and worried that being a pirate would be a thing of the past. In the lyrics, he is “a pirate, two hundred years too late.” He finds that there will be nothing to plunder anymore.

Buffett’s skillful storytelling makes this song an unforgettable journey into the nautical lifestyle. It paints a picture of a pirate who has spent much of his life sailing at sea.

18. “Sail Away” By Randy Newman

The piano ballad “Sail Away” by Randy Newman explores the dark side of the slave trade. The lyrics are filled with sarcasm and irony, reflecting the exploitation of African slaves.

The entire song is told from the perspective of a slaver who convinces his African slaves to “sail away” with him to the promised land: America. And in so doing, he presents America on her good side. There, they have food to eat, such as “sweet watermelon and the buckwheat cake.” They don’t have to deal with the perils of living in the jungle and wild animals.

The slaver furthers that in America, people are happy. The only thing that the Africans need to do is sail and cross the ocean with him.

19. “Ride Captain Ride” By Blues Image

The American rock band Blues Image released “Ride Captain Ride” in 1970, which became their only hit. Nevertheless, the song captures the excitement and adventure of sailing.

The lyrics tell the story of a captain and his crew of 73 setting sail on a journey across the ocean. They invite others to join them as they sail to a new land where they can be merry and “be free once more.”

Unfortunately, no one is interested because they are busy dealing with life’s troubles. And so the crew leaves on the mystery ship sailing to a land unknown. They are never heard from or seen again.

20. “Soul of a Sailor” By Kenny Chesney

Arguably the ultimate song celebrating life on the water is Kenny Chesney‘s “Soul of a Sailor.” At its core, it embodies the spirit and essence of a sailor’s life.

The lyrics follow the experiences of someone who loves the water. He is “born a son of the sea,” and he can’t imagine a life away from the ocean. It brings him a different joy when the wind guides his sail, and he allows the wind to take him anywhere it leads.

Overall, “Soul of a Sailor” celebrates the people who choose to dedicate their lives to sailing. It represents a journey consisting of challenges and rewards that come with navigating the open waters.

21. “Lost Sailor” By Grateful Dead

Sailing can be used literally and figuratively to explore our journey in life. This is the theme behind Grateful Dead‘s “Lost Sailor,” a song released in 1980.

The lyrics depict the stormy life of a sailor. He finds himself lacking direction and stability, as represented by the line, “Compass card is spinning, helm is swinging to and fro.” He feels lost, unable to find the dog star and the moon to guide him back home.

He’s been away too long that now he can’t see his path. He feels adrift, unable to determine his true purpose in life. The song reflects his yearning for meaning as he tries to regain a sense of direction.

22. “Ship To Wreck” By Florence + The Machine

Our next song, “Ship to Wreck” by Florence + The Machine, captures the emotions and struggles of the human experience. It takes you on a journey through personal introspection and self-destruction.

The title reflects the idea of one’s life spiraling out of control. When you’re in that situation, you end up destroying what you love most. This is like a ship crashing against treacherous rocks.

“Ship to Wreck” serves as a reminder that sometimes we must hit rock bottom before finding our way back up again. It speaks to anyone who has experienced moments of self-sabotage or felt overwhelmed by their own mistakes.

23. “If I Had A Boat” By Lyle Lovett

The whimsical and imaginative “If I Had a Boat” by Lyle Lovett is our next song on the list. It shows the power of dreams and one’s longing for adventure.

The song’s opening lyrics talk about what the narrator would do if he had a boat and a pony. One thing’s for sure: he’s going to ride his pony aboard his boat. While this may seem imaginative enough, it can be about his desire for freedom and escape from the mundaneness of life.

Another interpretation of the song is one’s yearning for a simpler but more adventurous existence. It’s about going after your dreams and embracing what lies ahead.

24. “Sailing To Philadelphia” By Mark Knopfler

The historical song “Sailing to Philadelphia” by Mark Knopfler tells the story of two men who embark on a journey to establish a border between Pennsylvania and Maryland in the new world.

In the lyrics, Jeremiah Dixon is described as a good surveyor, while Charles Mason is a stargazer. They have disagreements on the way until they get to Philadelphia to draw what they call the “Mason-Dixon Line.”

The song perfectly depicts the spirit of exploration and perseverance. It serves as an inspiration for anyone who has ever dreamed of setting sail toward their goals, symbolizing the determination and courage needed to overcome obstacles and reach new horizons.

25. “Sail Away” By Neil Young

Up next is Neil Young‘s “Sail Away,” released in 1979. This song is about one’s longing for escape and freedom from societal constraints.

Here, “sail away” is used metaphorically to break free from the limitations that society imposes. The lyrics evoke a sense of wanderlust, as Young sings about leaving behind the worries and troubles of everyday life to embark on a more meaningful adventure in search of a fulfilling existence.

In this context, the song is about aiming toward personal freedom. It’s about searching for a life that’s not about material possessions but about a simpler and more meaningful life.

26. “Sail On, Sailor” By The Beach Boys

Finally, we are at the end of our list with The Beach Boys‘ “Sail On, Sailor.” At its core, this song explores perseverance in the face of adversity.

As with any song, interpretations vary. But the lyrics seem to delve into the narrator’s resilience and determination to overcome trials and navigate through troubled waters.

The song uses the imagery of sailing to represent the journey in life. The narrator’s aim is to “wrest the waters, fight Neptune’s waters,” and face challenges head-on. He pushes forward and is resolved to sail on past the setbacks and hardships.

Summing Up Our List Of Sailing Songs

Now we’re at the end of our post, and we hope you liked what we have come up with today. We hope that you experienced how the songs above encapsulated the spirit of adventure and freedom associated with life on the open seas.

We suggest that you make a playlist of our compilation. So when you’re on a voyage or just chilling at home, you have some nice music to take you on a musical journey across the sea.

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Dan Farrant, the founder of Hello Music Theory, has been teaching music for over 15 years, helping hundreds of thousands of students unlock the joy of music. He graduated from The Royal Academy of Music in 2012 and then launched Hello Music Theory in 2014. He plays the guitar, piano, bass guitar and double bass and loves teaching music theory.