When you think of sailing, do you imagine pirates or luxury yachts? Musicians have written songs about every aspect of life at sea. These top sailing songs are perfect for hitting the open waves!
1. Lost Sailor — Grateful Dead
Grateful Dead’s song Lost Sailor is no longer widely known, largely because the band dropped it from live performances around 1986. The song describes a sailor lost at sea, unable to find the North Star or get his bearings. He dreamed of having the freedom of living life on the ocean, but now that he has lost his way, he realizes that freedom comes at the price of security.
2. Orinoco Flow — Enya
Irish singer Enya’s song Orinoco Flow is considered one of the best of her career, receiving two nominations for Grammy Awards. The song is an ode to sailing bound to get the blood pumping—and it’s not confined to any part of the world. It mentions watery locations worldwide, including Fiji and the Isles of Ebony. In case you were wondering about the title, the Orinoco is a 1,700-mile-long river that flows through Venezuela.
3. Son of a Son of a Sailor — Jimmy Buffett
Jimmy Buffett made an entire career around sailing and beach life, but one of his most famous songs was Son of a Son of a Sailor. The tune has become a staple of his concerts and is considered a favorite of his fanbase. It tells the story of a man who decides that the sea runs in his blood and embarks on the sea voyage of legends. All the classic sailing tropes are mentioned, from drinking rum to climbing the rigging.
4. Sloop John B — The Beach Boys
The world is familiar with Sloop John B thanks to the folk-rock cover by the Beach Boys in 1966. But the song is actually based on a Bahamian folk tune that has been around since at least 1916. It tells the story of a tragedy-fraught voyage on a sloop, which eventually runs aground in Nassau. At one point in the Bahamas, it was considered a beloved cultural song; the Beach Boys’ version gained widespread popularity thanks to its pop-infused, multilayered a cappella treatment.
5. Into The Mystic — Van Morrison
Into The Mystic is one of Van Morrison’s most famous songs, featured on his 1970 album Moondance. The song compares a sea voyage to a spiritual journey, with the narrator experiencing his oneness with the ocean and the sky around him. As he releases control over his journey, he sails forward “into the mystic” and realizes that he has set something in motion that he can no longer stop. The Irish singer paints a delightful contrast of physical and spiritual sensations.
6. Sailing — Rod Stewart
Sailing was originally recorded by The Sutherland Brothers Band in 1972, but it wasn’t until Rod Stewart’s cover three years later that it became widely known, hitting No. 1 in the UK. The song at first seems to be a love song about traveling across the sea to be reunited with a lover. However, toward the end, it becomes more apparent that the narrator is dying and comparing his journey into the next life to a sea voyage.
7. Captain Kennedy — Neil Young
Neil Young’s 1980 song Captain Kennedy tells the story of Captain Louis Kennedy, whose schooner was destroyed by German U-boats in 1941. Young met Kennedy in Nassau in the early 1970s and learned about his life’s experiences transporting cargo between the Caribbean and Canada, inspiring the song for his album Hawks & Doves.
8. Sailor’s Lament — Creedence Clearwater Revival
Creedence Clearwater Revival’s 1970 song Sailor’s Lament tells the story of a sailor who lost a card game with another member of the crew. The singer loses the game in the end, and the winner promises to “pick him clean.” It’s not entirely clear what happened after that, as the game is described as a duel. Did the loser of the game lose just his money or his life? It seems that anything can happen when you live on the open sea.
9. Paddy’s Green Shamrock Shore — The High Kings
Did you know that roughly 4.6 million Irish people immigrated to the US between 1820 and 1957? The High Kings’ emotional song Paddy’s Green Shamrock Shore imagines how an immigrant might feel, watching the coastline of Ireland disappear behind them.
Their stunningly powerful multipart harmony captures all the emotions of such an experience, from grief to determination, bravery, fear, and hope. In the final verse, they finally see the shoreline of New York appear on the horizon.
10. Wooden Ships — Crosby, Stills, Nash & Young
Wooden Ships was released in 1969 at the height of the Vietnam War. The song imagines the aftermath of the war, in which civilization has been destroyed. The only survivors are those who sail away on wooden ships to start a primitive but peaceful life away from the destruction. In a war made all the more deadly by new technology, one can imagine how the thought of escaping on an old-fashioned ship would be comforting.
11. When The Ship Comes In — Bob Dylan
When The Ship Comes In was one of Bob Dylan’s early hits, released on his 1964 album The Times They Are A-Changin’. The song describes a massive shift in the world, which affects the ocean and the tides. At first, the sea seems to hold its breath as though a hurricane is approaching—then the waters will rush in and drown the proud like in the story of Moses and the Red Sea. It sounds like an ominous story, but it was actually written in a fit of rage after Dylan was refused a hotel room for looking too dirty.
12. Soul of a Sailor — Kenny Chesney
In this day and age, sailor isn’t exactly a common profession. Not many people want to live their days on a boat with no permanent home or modern luxuries. Kenny Chesney’s 2005 song Soul of a Sailor laments the dying breed of sailors and tells the story of two men meeting one another in a bar. They immediately recognize the love of the sea in one another but also know that there aren’t many like them left in the world.
13. A Sailboat in The Moonlight — Billie Holiday
A Sailboat In The Moonlight has been recorded many times, but the best-known version was Billie Holiday’s cover in 1937. The sweet jazz song imagines a moonlit boat ride between two lovers, painting a vivid picture of the warm summer night breeze over the water. The singer dreams of sailing away with her lover, but for now, she’s content to enjoy the evening.
14. Single Handed Sailor — Dire Straits
Dire Straits’ song Single Handed Sailor is about two once-great ships, the Cutty Sark and the Gipsy Moth IV. There was a time when they were part of the British Royal Navy and “ruled the seas”; however, now they are on display in a museum and surrounded by concrete. The song cuts a remarkable contrast between the claims of the military ocean might and the fate of the ships. Despite all of Britain’s claims, the lyrics say, “nobody rules the waves.”
15. Sail Into The Sun — Gentlemen Hall
Gentlemen Hall’s song Sail Into The Sun wasn’t widely known until it was featured in a Target commercial. This increased its popularity, and people came to appreciate the stunning tune. The song imagines escaping with a loved one by “sailing into the sun” and describes what it would be like to float through an “ocean” of clouds and light. It paints an evocative picture, however you choose to interpret the lyrics.
16. Sail On — Commodores
Sail On is a breakup song that imagines saying goodbye for the last time at the docks. The singer invites their ex to sail on, implying that they are letting them go and there should be no hard feelings. It brings to mind the image of a river, which has a current and would therefore be difficult to sail back up. In other words, once the boat has sailed, there is no coming back.
17. Sailing — Christopher Cross
Christopher Cross’s 1979 song Sailing was a massive hit, racking up Grammy Awards and helping define the niche genre known as yacht rock. Cross’s experiences inspired the song in high school with a friend who took him sailing and served as a mentor for him during his difficult teenage years. It describes the peace and contentment of being out on a boat, which can either be interpreted literally or metaphorically (and Cross probably intended it to be both).
Recommended: Songs about boats/boating
18. Come Sail Away — Styx
Not every sailing song is necessarily about sailing on the ocean. The 1977 Styx song Come Sail Away plays on the word “spaceship” to describe “sailing” into outer space. The song tricks the listener for the first several verses, referencing a ship, a captain, and the sea. But before the final chorus, the song includes a twist: “We climbed aboard their starship, we headed for the skies.”
19. Sailin’ The Wind — Loggins & Messina
Sailors of the olden days relied on the wind to carry them where they needed to go. The 1973 song Sailin’ The Wind by duo Loggins & Messina is an ode to the wind. In this case, it’s a gentle breeze that keeps the ocean cool and helps children fly their kites. But the singer also imagines how pleasant it would be simply to let the wind take their boat wherever it pleases.
Recommended: Playlist of songs about the wind
20. Sail On, Sailor — The Beach Boys
Many songs about sailing describe a happy-go-lucky life of adventure. But the 1973 song Sail On, Sailor takes things in a different direction, telling the story of rough seas, lonely days, and frightening experiences on the water. It’s an unusual tack for the genre, particularly from the Beach Boys, who tended to produce songs that were extremely upbeat.
21. Sail Away — David Gray
Many singers have imagined what it would be like to “sail away” with their lover, escaping the world and its pressures and just living together with no responsibilities. It’s a trope as old as time and one that David Gray revisited in his 1998 hit Sail Away. Despite being done many times before, it’s clearly not tiring, as the song became an international hit.
22. Sailing Away — Chris de Burgh
Chris de Burgh’s 1988 song Sailing Away contrasts childhood dreams with growing up and wanting new things. The singer remembers how, as a child, he watched ships cross the horizon and dreamed of the places he could travel. Now that he’s grown up and fallen in love with a woman, he dreams instead of sailing into the night with her.
23. How Far I’ll Go — Auliʻi Cravalho
The 2016 Disney movie, Moana, told the story of a Polynesian girl who longed to learn how to sail on the ocean. In How Far I’ll Go, she imagines all the amazing adventures she could have beyond the horizon. The song became incredibly popular, both in its original film version and in the pop cover performed by Alessia Cara for the film credits.
24. Set Sail — The Movement
Set Sail is about a person who doesn’t feel like they have a home anywhere on land. They decide to board a ship to take them away somewhere new. Though the song is sad, it’s hard not to be moved by the description of the singer dancing on the beach, overjoyed at the sight of their ship coming in.
25. Play Crack The Sky — Brand New
Play Crack The Sky is a haunting song that tells the story of a shipwreck from the perspective of a sailor caught on board. It’s far from a happy song, and it’s not pleasant to imagine such an experience, but Brand New treats the tragedy with such stunning poetry that it is difficult to resist.
As the Head Editor and Writer at Music Grotto, Liam helps write and edit content produced from professional music/media journalists and other contributing writers. He works closely with journalists and other staff to format and publish music content for the Music Grotto website. Liam is also the founding member of Music Grotto and is passionate in disseminating editorial content to its readers.
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