Sailing has long been a symbol of freedom, adventure, and personal discovery, inspiring countless artists to weave this imagery into their songs. The act of setting sail, whether literal or metaphorical, evokes powerful emotions of escape, resilience, and exploration. Over the decades, musicians from diverse genres have used sailing as a motif to express everything from the yearning for peace and solitude to the struggle of overcoming life’s challenges.
Each song on this list carries its own unique interpretation of sailing, blending poetic lyricism with evocative melodies that transport listeners to the open seas. Whether navigating through love, loss, or life’s uncertainties, these Songs about sailing have left an indelible mark on the musical landscape, using the timeless metaphor of sailing to connect with audiences on a profound emotional level.
1. “Sail Away” by Randy Newman (1972)
About this song:
- Album: Sail Away
- Released: 1972
- Artist: Randy Newman
- Genre: Singer-songwriter
- Key Lyric: “Sail away, sail away, we will cross the mighty ocean into Charleston Bay.”
Randy Newman’s “Sail Away” was released as the title track of his third studio album in 1972.
The song satirically presents the perspective of a slave trader enticing Africans to sail to America with promises of prosperity.
Newman wrote this song to reflect on the darker elements of American history, using irony and sarcasm to expose the cruelty behind the American Dream.
Composed in a period of social upheaval, it resonates as a critique of the myths surrounding the nation’s foundation.
Its deceptively simple melody contrasts with its biting lyrical content, showcasing Newman’s distinctive style.
2. “Sail On” by The Commodores (1979)
About this song:
- Album: Midnight Magic
- Released: 1979
- Artist: The Commodores
- Genre: Soul, R&B
- Key Lyric: “Sail on down the line, ’bout-a half a mile or so.”
“Sail On” was released in 1979 as a major hit from The Commodores’ album Midnight Magic.
Written by Lionel Richie, the song addresses the end of a romantic relationship with a sense of peace and resignation.
Richie composed this piece as his own career was gaining momentum, using the metaphor of sailing to signify moving on and finding closure.
Its smooth blend of soul and R&B rhythms made it a standout track, showcasing Richie’s songwriting talents.
The song’s themes of transition and letting go resonated deeply with audiences, becoming one of the group’s most beloved tracks.
3. “Sailing” by Rod Stewart (1975)
About this song:
- Album: Atlantic Crossing
- Released: 1975
- Artist: Rod Stewart
- Genre: Rock, Pop
- Key Lyric: “I am sailing, I am sailing, home again, ‘cross the sea.”
Rod Stewart’s “Sailing” was released in 1975 and became one of his most iconic hits.
The song, written by Gavin Sutherland, evokes the longing for home and a deep connection to one’s roots through the metaphor of sailing.
It was composed during Stewart’s time of personal reflection, as he adjusted to life in America after moving from the UK.
With its emotional depth and grand orchestration, the song captures the universal feeling of searching for a sense of belonging.
“Sailing” became a symbol of hope and perseverance, topping the charts and remaining a timeless classic.
4. “Sail” by AWOLNATION (2011)
About this song:
- Album: Megalithic Symphony
- Released: 2011
- Artist: AWOLNATION
- Genre: Electronic Rock
- Key Lyric: “Sail! This is how I show my love.”
“Sail” by AWOLNATION was released in 2011 and quickly became a breakout hit.
The song is a raw expression of frustration, exploring themes of mental health, isolation, and the search for freedom.
Written by Aaron Bruno, it was composed during a period of personal and artistic struggle, with Bruno reflecting on societal pressures and personal demons.
The repetitive, almost hypnotic use of the word “sail” suggests a yearning for escape and release from internal turmoil.
Its fusion of electronic rock and introspective lyrics made it a unique anthem for a new generation of listeners.
5. “Sail into the Sun” by Gentlemen Hall (2013)
About this song:
- Album: When We All Disappear
- Released: 2013
- Artist: Gentlemen Hall
- Genre: Indie Pop
- Key Lyric: “Sail into the sun, sail into the sun, whoa.”
Gentlemen Hall’s “Sail into the Sun” was released in 2013 and quickly became a feel-good anthem.
The song encapsulates themes of optimism, adventure, and the joy of breaking free from routine.
Written by the band, the track came together during a creative surge as they experimented with uplifting and ethereal sounds.
Its bright melodies and upbeat tempo make it an embodiment of carefree, youthful exuberance, perfect for summer playlists.
The song’s light, breezy vibe captured the attention of commercials and films, helping to boost the band’s visibility.
6. “Sailin’ Shoes” by Little Feat (1972)
About this song:
- Album: Sailin’ Shoes
- Released: 1972
- Artist: Little Feat
- Genre: Rock
- Key Lyric: “Put on your sailin’ shoes, everyone will start to cheer.”
“Sailin’ Shoes” was released in 1972 on the album of the same name by Little Feat.
The song blends rock and southern boogie, reflecting themes of escape and personal freedom.
Written by bandleader Lowell George, the track came at a time when George was exploring more surreal and introspective lyrics.
Its playful yet melancholic tone, combined with quirky storytelling, makes it a signature Little Feat song.
The song became a cult favorite, showcasing George’s songwriting and the band’s unique style.
7. “Sail Away Sweet Sister” by Queen (1980)
About this song:
- Album: The Game
- Released: 1980
- Artist: Queen
- Genre: Rock
- Key Lyric: “Sail away sweet sister, sail across the sea.”
Released in 1980, Queen’s “Sail Away Sweet Sister” is a lesser-known gem from The Game album.
The song was written and sung by Brian May, offering a tender ballad in contrast to the band’s heavier rock hits.
The lyrics speak of loss and reconciliation, symbolizing the emotional departure of a loved one.
May composed it during a period of personal introspection, balancing Queen’s bombastic stage presence with a more reflective side.
Though it wasn’t released as a single, the track has earned a special place in the hearts of Queen fans.
8. “Sail on Sailor” by The Beach Boys (1973)
About this song:
- Album: Holland
- Released: 1973
- Artist: The Beach Boys
- Genre: Surf Rock, Pop
- Key Lyric: “Sail on, sail on, sailor.”
“Sail on Sailor” was released in 1973 as part of The Beach Boys’ Holland album.
Written by a team including Brian Wilson and Van Dyke Parks, the song reflects perseverance in the face of life’s challenges.
It was composed during a turbulent time for the band, with internal struggles and creative differences affecting their music.
The song’s uplifting message and soulful delivery by lead singer Blondie Chaplin stand in contrast to its troubled production.
Despite its challenging birth, “Sail on Sailor” became one of The Beach Boys’ most enduring songs.
9. “Sail Away” by David Gray (2000)
About this song:
- Album: White Ladder
- Released: 2000
- Artist: David Gray
- Genre: Folk Rock
- Key Lyric: “Sail away with me honey, I put my heart in your hands.”
David Gray’s “Sail Away” was released in 2000 as part of his breakthrough album White Ladder.
The song is a delicate, emotive ballad, expressing themes of love, longing, and the desire to escape together.
Gray wrote it during a period of artistic renewal, drawing inspiration from his personal relationships and the changes in his life.
Its stripped-back acoustic arrangement highlights the sincerity and vulnerability in the lyrics.
“Sail Away” became a fan favorite, solidifying Gray’s place in the singer-songwriter genre.
10. “Sail the Wildest Stretch” by Powderfinger (2009)
About this song:
- Album: Golden Rule
- Released: 2009
- Artist: Powderfinger
- Genre: Alternative Rock
- Key Lyric: “Sail the wildest stretch of water, know that nothing lasts forever.”
Powderfinger released “Sail the Wildest Stretch” in 2009 as part of their Golden Rule album.
The song explores the concept of journeying into the unknown, embracing change, and accepting life’s impermanence.
It was written during the band’s final years together, capturing the bittersweet emotions of impending farewells.
Lead vocalist Bernard Fanning’s reflective lyrics are complemented by the band’s signature sweeping rock sound.
“Sail the Wildest Stretch” became a fitting farewell as the band announced their split shortly after the album’s release.
11. “Sailing to Philadelphia” by Mark Knopfler (2000)
About this song:
- Album: Sailing to Philadelphia
- Released: 2000
- Artist: Mark Knopfler
- Genre: Rock, Folk
- Key Lyric: “We are sailing to Philadelphia, to draw the line, the Mason-Dixon line.”
Mark Knopfler’s “Sailing to Philadelphia” was released in 2000 as the title track of his second solo album.
The song is a historical ballad, inspired by Thomas Pynchon’s novel Mason & Dixon, focusing on the two British surveyors who charted the Mason-Dixon line.
Knopfler composed this song to blend folk storytelling with historical narrative, capturing the journey of discovery and division in American history.
Its soft guitar riffs and poetic lyrics create a reflective atmosphere, exploring themes of exploration and boundaries.
“Sailing to Philadelphia” showcases Knopfler’s skillful blend of music and history, making it a standout in his solo career.
12. “Sail Away” by Enya (2000)
About this song:
- Album: A Day Without Rain
- Released: 2000
- Artist: Enya
- Genre: New Age, Celtic
- Key Lyric: “Sail away, sail away, sail away.”
Enya’s “Sail Away” (also known as “Orinoco Flow”) was released as part of her 2000 album A Day Without Rain.
The song evokes feelings of escape and tranquility, with its ethereal soundscape and Enya’s signature layered vocals.
Composed during a period of creative rejuvenation, Enya was inspired by both the beauty of nature and the desire to escape the pressures of modern life.
The repetitive “sail away” phrase adds to the hypnotic, meditative quality of the song, inviting listeners to drift away mentally.
Its peaceful, otherworldly sound helped cement Enya’s reputation as a leader in New Age music.
13. “Sailing” by Christopher Cross (1979)
About this song:
- Album: Christopher Cross
- Released: 1979
- Artist: Christopher Cross
- Genre: Soft Rock
- Key Lyric: “Sailing takes me away to where I’ve always heard it could be.”
Christopher Cross released “Sailing” in 1979, and it quickly became one of his signature hits.
The song is about the emotional release and sense of peace that comes from sailing, symbolizing personal freedom and tranquility.
Cross composed the song during a reflective period in his life, inspired by his own love for sailing and the calm it brought him.
Its smooth, serene sound, paired with introspective lyrics, resonated deeply with listeners, earning it multiple Grammy Awards.
“Sailing” remains a classic example of soft rock, cherished for its ability to transport listeners to a place of serenity.
14. “Set Sail” by The Movement (2008)
About this song:
- Album: The Movement
- Released: 2008
- Artist: The Movement
- Genre: Reggae rock
- Key Lyric: “Sail on, sail on, my friend, sail on.”
“Set Sail” by The Movement, released in 2008, is a reggae rock song that encourages listeners to pursue their dreams and aspirations.
The song was written by the band’s members as an anthem of empowerment and positivity.
“Set Sail” features a laid-back groove, catchy hooks, and uplifting lyrics that inspire action and determination.
Recorded with a blend of reggae rhythms and rock elements, the track showcases The Movement’s signature sound.
Its motivational message and infectious energy make “Set Sail” a favorite for fans of feel-good music.
15. “Sail Away” by Tom Harrell (1991)
About this song:
- Album: Sail Away
- Released: 1991
- Artist: Tom Harrell
- Genre: Jazz
- Key Lyric: (Instrumental)
Tom Harrell’s Sail Away, released in 1991, is a masterful jazz composition that stands out as a notable work in his career.
Though it is an instrumental piece, the title evokes themes of freedom and emotional release, as the music guides the listener through a journey of improvisation and beauty.
Harrell composed the album during a time when his abilities as a jazz trumpeter and composer were reaching their peak, balancing complexity with emotional resonance.
The song’s flowing melodies and sophisticated harmonies give the impression of being carried away by the music, much like a ship sailing on calm waters.
“Sail Away” represents Harrell’s brilliance in jazz composition, with a focus on mood and movement rather than lyrical content.
16. “Sailing Shoes” by Robert Palmer (1974)
About this song:
- Album: Sneakin’ Sally Through the Alley
- Released: 1974
- Artist: Robert Palmer
- Genre: Funk Rock
- Key Lyric: “Put on your sailin’ shoes, everyone will start to cheer.”
Robert Palmer’s version of “Sailing Shoes” was released in 1974 as part of his debut album Sneakin’ Sally Through the Alley.
The song, originally written by Lowell George of Little Feat, was reimagined by Palmer with a funky, energetic twist.
Palmer’s interpretation reflects his eclectic approach to music, blending rock, funk, and soul to create a unique sound.
“Sailing Shoes” is a playful, carefree song that captures the essence of Palmer’s adventurous spirit during his early career.
This version helped introduce Palmer’s dynamic style to the world, making it a standout track in his discography.
17. “Sailor” by Petula Clark (1961)
About this song:
- Album: Sailor
- Released: 1961
- Artist: Petula Clark
- Genre: Pop
- Key Lyric: “Sailor, stop your roaming, Sailor, leave the sea.”
Petula Clark’s “Sailor” was released in 1961, marking one of her early international hits.
The song tells the story of a woman longing for her lover to return from the sea, expressing themes of love, separation, and hope.
Written by Werner Scharfenberger and Fini Busch, the song was a hit in several countries, showcasing Clark’s versatility as a pop vocalist.
Its heartfelt lyrics and catchy melody resonated with audiences, especially during a time when many faced the emotional toll of long-distance relationships.
“Sailor” helped solidify Clark’s status as a global pop star, leading to a series of successful singles in the 1960s.
18. “Sail the Waterway” by Steely Dan (1972)
About this song:
- Album: (Non-album single)
- Released: 1972
- Artist: Steely Dan
- Genre: Jazz Rock
- Key Lyric: “Sail the waterway, got nothing to lose.”
“Sail the Waterway” was released in 1972 as Steely Dan’s debut single, though it did not make it onto any of their albums.
The song showcases early elements of the band’s jazz-rock fusion, with cryptic lyrics and a complex musical arrangement.
It was composed by Walter Becker and Donald Fagen, reflecting their experimental approach to blending different genres in their early work.
While it wasn’t a commercial success, “Sail the Waterway” helped lay the groundwork for the sophisticated sound Steely Dan would later become known for.
Its rarity in the band’s catalog makes it a hidden gem for fans of their early music.
19. “Sailboat” by The Submarines (2008)
About this song:
- Album: Honeysuckle Weeks
- Released: 2008
- Artist: The Submarines
- Genre: Indie Pop
- Key Lyric: “We’re sailing in a sailboat, down the waterway of life.”
The Submarines released “Sailboat” in 2008 as part of their Honeysuckle Weeks album.
The song is a whimsical and tender love song, using the metaphor of sailing to describe the journey of a relationship.
Blake Hazard and John Dragonetti, the duo behind the band, wrote it during a period of personal and professional collaboration, capturing their shared experiences.
Its dreamy melodies and soft, indie-pop instrumentation give it a serene, reflective quality, making it a fan favorite.
“Sailboat” is a perfect example of the duo’s ability to turn everyday moments into lyrical, emotional music.
20. “Sail” by DevilDriver (2009)
About this song:
- Album: Pray for Villains
- Released: 2009
- Artist: DevilDriver
- Genre: Groove Metal
- Key Lyric: “Sail with me into the dark waters.”
DevilDriver’s “Sail” was released in 2009 as part of their Pray for Villains album.
The song presents a darker, more aggressive take on the concept of sailing, symbolizing a journey into the unknown and dangerous territories of life.
Written during a time of personal and societal turmoil, the band infused the song with themes of rebellion, defiance, and survival.
Its heavy riffs and intense energy reflect the band’s signature groove metal sound, appealing to fans of harder, more intense music.
“Sail” stands out as one of the band’s most powerful and atmospheric tracks, embodying a sense of boldness and risk.
21. “Sailing on the Seven Seas” by Orchestral Manoeuvres in the Dark (1991)
About this song:
- Album: Sugar Tax
- Released: 1991
- Artist: Orchestral Manoeuvres in the Dark (OMD)
- Genre: Synth-pop
- Key Lyric: “Cause I’m sailing on the seven seas so blue.”
OMD’s “Sailing on the Seven Seas” was released in 1991 on their Sugar Tax album.
The song marks a high-energy return for the band after a brief hiatus, blending their signature synth-pop sound with more upbeat, rock elements.
Lyrically, it evokes a sense of freedom and adventure, symbolizing exploration and breaking away from constraints.
Written during a period of personal and professional reinvention for the band, the track reflects their desire to push boundaries and experiment with their sound.
It became a hit in both the UK and Europe, re-establishing OMD’s place in the evolving electronic music scene of the early ’90s.
22. “Sailing Ships” by Whitesnake (1989)
About this song:
- Album: Slip of the Tongue
- Released: 1989
- Artist: Whitesnake
- Genre: Soul, R&B
- Key Lyric: “You’re the one who holds the key. Or sailing ships will pass you by.”
Released in 1989, “Sailing Ships” by Whitesnake is a hard rock ballad that uses sailing as a metaphor for life’s journeys and challenges.
The song was written by David Coverdale and Adrian Vandenberg during a time of reflection and change.
“Sailing Ships” features powerful vocals, emotive guitar work, and a dramatic arrangement that captures the song’s epic nature.
Recorded during the late ’80s rock scene, the track stands out for its introspective lyrics and dynamic sound.
With its timeless theme and emotional depth, “Sailing Ships” remains a beloved track for Whitesnake fans.
23. “Sail Away” by Deep Purple (1974)
About this song:
- Album: Burn
- Released: 1974
- Artist: Deep Purple
- Genre: Hard Rock
- Key Lyric: “Sail away tomorrow, sailin’ far away.”
Deep Purple’s “Sail Away” was released in 1974 on their Burn album, marking a new chapter for the band with David Coverdale on vocals.
The song blends hard rock with a funky groove, capturing the band’s experimentation with different musical influences at the time.
Written by Ritchie Blackmore and David Coverdale, the track focuses on themes of escape and freedom, with the lyrics suggesting the desire to break free from limitations.
It was composed during a time when the band was exploring new dynamics following significant lineup changes.
“Sail Away” became a fan favorite, representing the band’s ability to evolve while maintaining their signature powerful sound.
24. “Sailor Song” by Regina Spektor (2004)
About this song:
- Album: Soviet Kitsch
- Released: 2004
- Artist: Regina Spektor
- Genre: Indie Pop
- Key Lyric: “Mary Ann’s a sailor, a sailor sailing away.”
Regina Spektor’s “Sailor Song” was released in 2004 as part of her Soviet Kitsch album, marking her rise in the indie music scene.
The song is a quirky, narrative-driven piece, blending folk and pop elements while telling the story of a sailor and those left behind.
Spektor wrote it during a creative period when she was experimenting with unconventional song structures and whimsical storytelling.
The playful piano melody juxtaposes the melancholic lyrics, showcasing Spektor’s ability to blend humor and depth in her songwriting.
“Sailor Song” became one of the standout tracks from the album, highlighting Spektor’s unique style and lyrical approach.
25. “Red Sails in the Sunset” by Nat King Cole (1951)
About this song:
- Album: Little Child / Red Sails In The Sunset
- Released: 1951
- Artist: The Steve Miller Band
- Genre: Psychedelic Rock
- Key Lyric: “Red sails in the sunset, way out on the sea.”
Released in 1951, “Red Sails in the Sunset” by Nat King Cole is a jazz standard that evokes the romantic imagery of sailing into the sunset.
The song was written by Jimmy Kennedy and Hugh Williams, and Cole’s rendition became one of its most beloved interpretations.
“Red Sails in the Sunset” features Cole’s smooth, velvety voice and a lush orchestral arrangement that adds to its nostalgic charm.
The track’s lyrics paint a vivid picture of a serene and beautiful evening at sea, capturing the imagination of listeners.
With its timeless appeal and evocative imagery, “Red Sails in the Sunset” remains a classic in the jazz repertoire.
26. “Sail Away” by Great White (1994)
About this song:
- Album: Sail Away
- Released: 1994
- Artist: Great White
- Genre: Hard Rock, Blues Rock
- Key Lyric: “Come sail away, come sail away with me.”
Great White’s “Sail Away” was released in 1994 as the title track of their bluesy hard rock album.
The song reflects themes of longing, escape, and the desire to find solace in distant places.
Written during a time when the band was navigating personal and professional changes, it offers a more introspective take compared to their earlier, heavier tracks.
Its acoustic-driven sound and emotional depth showcase the band’s versatility and ability to tap into softer, more reflective material.
“Sail Away” became a favorite among fans of the band’s more balladic side, showing their range beyond typical rock anthems.
27. “Sailin’ the Wind” by Loggins & Messina (1973)
About this song:
- Album: Full Sail
- Released: 1973
- Artist: Loggins & Messina
- Genre: Soft Rock, Folk Rock
- Key Lyric: “We’re sailin’ the wind, straight through the storm.”
Loggins & Messina’s “Sailin’ the Wind” was released in 1973 on their album Full Sail.
The song is a metaphorical exploration of navigating life’s storms, reflecting the duo’s folk and soft rock influences.
Written by Kenny Loggins and Jim Messina, it captures a sense of freedom and resilience in the face of life’s challenges.
Its harmonious blend of acoustic guitar and lush instrumentation became a hallmark of the duo’s signature sound.
“Sailin’ the Wind” became a favorite among fans, representing their optimistic and uplifting approach to songwriting.
28. “Sailor’s Lament” by Creedence Clearwater Revival (1970)
About this song:
- Album: Pendulum
- Released: 1970
- Artist: Creedence Clearwater Revival
- Genre: Rock
- Key Lyric: “Oh sailor, why’d you sail away?”
Creedence Clearwater Revival’s “Sailor’s Lament” was released in 1970 on their Pendulum album.
The song uses the metaphor of a sailor lost at sea to address themes of regret, loss, and the inevitability of fate.
Written by John Fogerty, it was composed during a period of increasing tension within the band, reflecting some of the inner struggles the members faced.
Its bluesy undertones and moody lyrics offer a darker, introspective side of the band’s sound compared to their more upbeat hits.
“Sailor’s Lament” became a deep cut for fans who appreciated CCR’s more reflective and melancholic tracks.
29. “Sail Away Ladies” by Odetta (1959)
About this song:
- Album: At The Gate Of Horn
- Released: 1959
- Artist: Odetta
- Genre: Blues, Folk
- Key Lyric: “Don’t you rock it Daddy-oh.”
Released in 1959, “Sail Away Ladies” by Odetta is a traditional folk song that captures the spirit of adventure and freedom associated with sailing.
The song was arranged by Odetta, who brought her powerful voice and unique interpretation to this classic tune.
“Sail Away Ladies” features Odetta’s soulful vocals, acoustic guitar, and a rhythmic arrangement that adds to its lively feel.
The track’s lyrics celebrate the joy of sailing and the sense of liberation it brings, resonating with listeners who share this passion.
With its timeless appeal and spirited performance, “Sail Away Ladies” remains a beloved folk classic.
30. “Sailor’s Boots” by Frank Turner (2010)
About this song:
- Album: Rock & Roll EP
- Released: 2010
- Artist: Frank Turner
- Genre: Folk Punk
- Key Lyric: “These old sailor’s boots have carried me far.”
Frank Turner’s “Sailor’s Boots” was released in 2010 as part of his Rock & Roll EP.
The song tells the story of a weary traveler who has been worn down by the journey, using the metaphor of well-worn boots to symbolize a life of experience.
Turner composed this track during a period of extensive touring, reflecting the physical and emotional toll of constant travel and performance.
Its stripped-down acoustic style and heartfelt lyrics exemplify Turner’s blend of folk storytelling with punk energy.
“Sailor’s Boots” became a fan favorite for its authenticity and connection to Turner’s own life on the road.
Conclusion
The imagery of sailing has proven to be a timeless and versatile metaphor in music, capturing the essence of personal journeys, emotional depth, and human resilience. From peaceful reflections on life’s calm moments to powerful anthems of escape and exploration, songs about sailing have connected with listeners in profound and diverse ways. Whether artists are using sailing as a symbol of freedom or a means to express struggle, each track adds a unique dimension to this rich tradition in songwriting.
The enduring popularity of songs about sailing across genres highlights the universal appeal of the sea as a metaphor for life’s challenges and triumphs. In the end, the act of sailing, with all its unpredictability and beauty, continues to resonate deeply in music, inviting us to navigate our own paths and embrace the journey.