23 Songs about Sailing to Enjoy on Your Voyage

Sailing ranges from peaceful vacations on the beach to treacherous journeys on the raging sea. Sailing songs also vary greatly.

While bands like Dire Straits have covered historic sailing journeys in their songs in the past, musicians such as Bob Dylan have used stormy seas and raging winds as metaphors for tough times.

This list of songs about sailing is rich in story-telling and is full of thought-provoking and inspirational tunes.

Sailing – Rod Stewart

Originally written by the Sutherland Brothers, Rod Stewart decided to record ‘Sailing’ in 1975 when he was experiencing homesickness after his recent move to the US from the UK. He recorded the album the tune is featured on, Atlantic Crossing, at the famous Muscle Shoals recording studio in Alabama, made popular by the many prominent artists who’ve recorded there, including southern rock band Lynyrd Skynyrd.

Related: Hear more great songs about missing home.


Castaway – Zac Brown Band

“I wanna be a castaway and leave the world behind.” Country group Zac Brown Band took a page out of Jimmy Buffett’s book and released several tropical-themed country hits. ‘Castaway’ tells the story of a man who wants to get away from it all and sail away to the Caribbean. A key influence for band leader Zac Brown, he’s previously mentioned his love of Bob Marley’s music had a profound effect on his own songwriting, especially regarding reggae-themed songs like ‘Castaway.’

Related: Check out our playlist of songs about the beach.


A Pirate Looks at Forty – Jimmy Buffett

Written by Jimmy Buffett at the young age of 27, ‘A Pirate Looks at Forty’ is a tale about life’s transitions as one gets older. He drew inspiration for the tune from a modern-day pirate, Phil Clark, who Buffett got to know well while living in Key West. During one of their conversations, Clark confessed to Buffett that he didn’t know how much longer his line of work would be around, which had him questioning what he would do with the rest of his life.

Related: Find this tune on our list of songs with numbers in the lyrics.


Sloop John B – The Beach Boys

The most famous version of ‘Sloop John B’ was released on The Beach Boy’s famous album Pet Sounds in 1966. But long before that release, the tune about a shipwreck was simply known as a “traditional West Indies” song. The popular band, The Kingston Trio, got hold of it and released their own version, which caught the attention of Brian Wilson (The Beach Boys’ main songwriter). They changed a few lyrics and some instrumentation to give it a modern folk sound.

Related: You can hear this song on our playlist of Forrest Gump songs.


Sailor’s Lament – Creedence Clearwater Revival

When southern rock band Creedence Clearwater Revival released ‘Sailor’s Lament’ on their sixth studio album, Pendulum, they took a more folksy approach with the tune, adding in harmonies from the whole group and acoustic percussion. The band spent more time recording Pendulum than they had for any previous album, and they spent a significant portion of their recording time on the production of ‘Sailor’s Lament,’ though it was never released as a single.


When the Ship Comes In – Bob Dylan

“Like the stillness in the wind. Before the hurricane begins. The hour that the ship comes in.” This powerful tune full of vengeance debuted on Bob Dylan’s popular The Times They Are A-Changin’ album. The song was written by Dylan during a fit of emotion when a hotel manager refused to give him a room because he looked like he could be bad news. Only after fellow artist, Joan Baez vouched for him was he able to get a room.

Related: See more on our hurricane songs list.


Wooden Ships – Crosby, Stills, Nash & Young

In the 1950s and ’60s, the US was not only engaged in a vast amount of nuclear weapons testing, but the Cold War between America and the Soviet Union was gaining significant ground. Because of this, the fear of nuclear attack constantly hung over the American population. Released in 1969, Crosby, Stills, Nash, and Young’s ‘Wooden Ships’ explores what life would be like in the event of a nuclear holocaust.

Related: Listen to our end of the world songs playlist.


Sail Away – David Gray

“Sail away with me, honey.” Songwriter David Gray refers to ‘Sail Away’ as a “Frankenstein song” because it took him years to write and eventually became a mashup of many different verses and lyrics. The song was released after his label dropped him, but the ensuing popularity of the song in America, the UK, and Ireland eventually helped it go platinum.


Soul of a Sailor – Kenny Chesney

“He walked in with a salty sway. Lookin’ like Blackbeard in his day.” This 2005 release finds country crooner Kenny Chesney singing about his life spent on the water. Likening himself to a pirate like Blackbeard, he chats with a fellow sailor at the bar as they trade stories and talk about how they’re “both a dying breed.”

Related: Splash over to our songs about water playlist.


Sailing – Christopher Cross

Songwriter Christopher Cross’s song was inspired by his younger days sailing in Texas after playing around with alternate tunings on his guitar. The tune became a popular song in a larger subgenre of “Yacht Rock,” a type of easy-listening music well-to-do people loved to play while hanging out on their boats. The song reached the top spot on American charts in 1980.


A Sailboat in the Moonlight – Billie Holiday

This vintage 1937 tune by Billie Holiday and her orchestra was written by the songwriting team John Jacob Loeb and Carmen Lombardo. The jazzy-pop song featuring saxophone by Lester Young shows Holiday’s range and ability to connect with listeners while telling a story. ‘A Sailboat in the Moonlight’ was one of several tunes Young and Holiday recorded together.

Related: Head over to our playlist of moonlight songs.


Single Handed Sailor – Dire Straits

Dire Strait’s ‘Single Handed Sailor’ tells the story of Sir Francis Chichester, one of the few sailors to circumnavigate the globe. It took him about a year to complete his mission after embarking on his journey from Plymouth, MA. The song is full of references to his journey, such as “You never want to fight against the river law. Nobody rules the waves.”


Lost Sailor – Grateful Dead

Often associated with another Grateful Dead tune (‘Saint of Circumstance’), ‘Lost Sailor’ combines themes of unsettled weather, dogs, and gambling to tell powerful stories about feeling lost in life. Written by Bob Weir and John Barlow in 1979, it was released on the Grateful Dead’s 1980 album Go To Heaven.

Related: You’ll want to “sea” our list of ocean songs.


Captain Kennedy – Neil Young

Written in honor of expert mariner and soldier Captain Louis Kennedy, the song centers around his life on the water and his time spent in war. The historical and personal song appears on Neil Young’s 1980 album Hawks and Doves. The A side of the album featured gentler tunes to go along with the “doves” theme, and the B side featured stronger songs in keeping with the “hawks” theme.

Related: You might hear about hawks and doves on our list of the best bird songs.


Only the Ocean – Jack Johnson

Though Jack Johnson has become a famous songwriter hailing from Hawaii, his father, Jeff Johnson, was a famous surfer. Jack’s song ‘Only the Ocean’ was written when he was reflecting on his father’s life spent riding waves. He also used water symbolism in the song to represent one’s subconscious. It’s the last song on his 2010 album To The Sea.

Related: Splash over to more songs about oceans.


I’m on a Boat – The Lonely Island

Featured on their 2009 album Incredibad, The Lonely Island trio is comprised of comedians Akiva Schaffer, Andy Samberg, and Jorma Taccone. The song’s popularity gained significant traction after the actor and bandmate Andy Samberg used it in one of his many popular “digital shorts” segments on the popular sketch comedy show Saturday Night Live.


If I Had a Boat – Lyle Lovett

A traditional Lyle Lovett tune off his 1987 album Pontiac, his song ‘If I Had a Boat’ was based on actual events. It tells the story of Lovett wishing he had a boat as he tries to cross a body of water on horseback. Though the album was a bit explorative musically (it gained him a cross-genre audience), songs like this one kept fans of his original sound happy.


Southern Cross – Crosby, Stills & Nash

Penned during a co-writing session with songwriting duo The Curtis Brothers, Crosby, Stills, & Nash highlight a famous constellation in ‘Southern Cross.’ This grouping of stars is one of the most important in the night sky, helping sailors navigate choppy waters for ions. Several of the stars in the constellation form a cross in the southern hemisphere, giving it the appropriate name, Southern Cross.

Related: Enjoy this star songs playlist while you identify constellations.


Sail on Sailor – The Beach Boys

“I sailed an ocean. Unsettled ocean.” In 1973, a core member of The Beach Boys, Brian Wilson, was becoming increasingly unpredictable and hard to work with. His friend, fellow songwriter, and collaborator Van Dyke Parks was one of the only people still able to work with Wilson directly. ‘Sail on Sailor’ was born from a session he conducted with Wilson when Warner Bros. record company demanded a single from the band for their album to be released that year, Holland.

Related: This song features on our playlist of the best profession songs.


A Sailor’s Life – Fairport Convention

“A sailor’s life, it is a merry life.” ‘A Sailor’s Life’ is an often covered folk song that regained popularity in the mid-60s in the UK during the folk revival years. It tells the tale of a young girl in search of her true love, a sailor, though his love for the roaring seas means he’s often away. Fairport Convention released a popular cover of the song in 1969.


Sailing Away – Chris de Burgh

“I was just a boy, dreaming of the wide world.” This romantic tune opens with Chris de Burgh detailing childhood memories of watching ships sail away and dreaming of all the places he hadn’t been. As the song progresses, he gets older and falls in love. His dreams of sailing turn into dreams of sailing away with the one he loves.

Related: Drift away with our list of dream songs.


Come Sail Away – Styx

A popular Styx song that climbed all the way to number eight on American charts was written by band keyboardist Dennis DeYoung. The song’s lyrics are uplifting, beckoning the listener to “Come sail away” to new adventures. DeYoung’s inspiration for the song came as he struggled in the music industry to make it in his early days with Styx.


Sailing on the Seven Seas – OMD

A popular hit song for Orchestral Manoeuvres in the Dark, or OMD, the English electronic band released ‘Sailing on the Seven Seas’ as a single from their album Sugar Tax in 1991. The rocking tune was written as a tribute to several artists and bands dear to them, including The Velvet Underground, The Who, and Andy McCluskey.


More songs about sailing:

  • Cool Change – Little River Band
  • Into the Mystic -Van Morrison
  • Shipbuilding – Elvis Costello