23 Best Songs About Sailing

The best songs about sailing evoke the feeling of escaping life’s troubles and taking to the seas for an adventure into the unknown. 

As a fixture of the music scene since the earliest sea shanty was sung, it’s a topic many bands and singers have since approached in their work. 

Continue reading, and we’ll break down the most significant songs exploring the sailing experience you can listen to when you’re in the mood to escape life’s problems. 

The 23 Best Songs About Sailing 

Whether you’re looking for classic sea shanties or contemporary music about adventures on the ocean waves, there’s a sailing song that caters to your taste. 

We’ve crafted this playlist to bring you an eclectic mix of sailing-themed songs from some of the most iconic singer-songwriters and bands of all time. 

Without further ado, here’s our playlist of the 23 best songs about sailing. 

23. “Sail On” – The Commodores 

Before breaking out into his hugely successful solo career, Lionel Ritchie enjoyed many hit releases as a member of the Commodores during the 1970s. 

“Sail On” is one of the more memorable songs about sailing and a classic example of the Commodores’ knack for producing beautiful ballads. 

Released on their 1979 album Midnight Magic, “Sail On” was one of three singles released from the long player, carried by Ritchie’s country-infused vocals.

22. “Cool Change” – Little River Band 

Also released in 1979 was the soft rock song “Cool Change” by Little River Band, written by the lead singer of the Australian rock band Glenn Shorrock. 

It’s a beautifully understated piece of music that evokes life on the sea and is a must for anyone looking for classic sailing songs to add to their playlist. 

The song’s lyrics evoke a yearning for open waters, watching the whales and dolphins, and the sense of connection with nature this experience brings. 

21. “Southern Cross” – Crosby, Stills & Nash 

In stark contrast to “Take the Money and Run,” Crosby, Stills, and Nash’s great song about greed, “Southern Cross” offers a more laid-back vibe by the band. 

This classic song is based on “Seven League Boots” by Rick and Michael Curtis, albeit with a different chorus and a basis in reality. 

Stills wrote “Southern Cross” after taking a long trip on a boat following a divorce to share how he used the power of the universe to heal emotional wounds. 

20. “A Sailor’s Life” – Fairpoint Convention 

“A Sailor’s Life” by Fairpoint Convention is another folk-inspired classic from the late 1960s that has a nostalgic undertone to its lyrics. 

It’s a heartfelt and touching ode to the life of a sailor on the high seas, revolving around a young woman’s attempts to find her lost lover. 

This catchy tune was released on the Fairpoint Convention album Unhalfbricking, marking the band’s shift from American-style folk to traditional English influences. 

19. “Drunken Sailor” – Irish Rovers 

Even those not especially interested in folk music and its vibrant history will no doubt be familiar with “Drunken Sailor” by the Irish Rovers. 

This is a classic piece of sailing music that uses an old folk song and brings it into the modern era, and it’s one of the finest sea shanties ever written. 

No sailing playlist is complete without “Drunken Sailor,” a loving testament to the trials and tribulations experienced by sailors throughout the ages on the seven seas. 

18. “Sailboat” – Ben Rector 

Nashville-based singer-songwriter Ben Rector’s song “Sailboat” brings us up to date with a modern-day take on the sailing experience. 

Released in 2022, “Sailboat” features lyrics that use a sailing ship as a metaphor for being lost and disorientated in life, struggling to find direction. 

Ben Rector released “Sailboat” on his album Symphony Sessions, showcasing the evolution in his singing and songwriting abilities. 

17. “Come Sail Away” – Styx 

Several years after releasing their moving song about time, “Too Much Time on My Hands,” Styx turned their progressive rock music skills to sailing with “Come Sail Away.” 

This lush and moving song stands as a testament to the spirit of escape, using elements of ballads combined with bombastic guitars. 

Regarded as one of the best power ballads of the era and one of the greatest tracks by Styx, “Come Sail Away” was featured on The Grand Illusion. 

16. “Sail On, Sailor” – The Beach Boys 

Our first of two songs about sailing from the Beach Boys featured on this playlist is “Sail On, Sailor,” taken from their 1973 album Holland. 

This song is quintessential of the Beach Boys, utilizing their trademark harmonies, fluid percussion, and stirring guitar riffs. 

Fitting comfortably in the classic rock genre, “Sail On, Sailor” established its growing talent even if it failed to light up the charts at its release. 

15. “Sailing Away” – Chris de Burgh

Chris de Burgh enjoyed a hugely successful career making commercially appealing rock music with elements of pop that increased their mass appeal. 

“Sailing Away” is an excellent example of what makes him so appealing, with easy-to-follow lyrics and a catchy melody anyone can hum along with. 

Released in 1988, “Sailing Away” by Chris de Burgh was released on the album Flying Colors, which included the popular single “Missing You.” 

14. “When the Ship Comes In” – Bob Dylan 

Bob Dylan, one of the most prolific singer-songwriters of his generation, has produced some of the best songs of all time over the last few decades. 

“When the Ship Comes In” is among his best works, a beautiful, haunting song that describes a stillness crossing the ocean. 

Released on The Times They Are a-Changin album, “When the Ship Comes In” ranks among the most touching and incredible songs on the subject. 

13. “Only the Ocean” – Jack Johnson 

Jack Johnson brings his touch of folk music to the table with “Only the Ocean,” which also features rock and indie music elements. 

Released with a gorgeous music video, “Only the Ocean” is another powerful song about sailing and the sea that captures the spirit of setting out on an adventure. 

Jack Johnson released “Only the Ocean” on the aptly titled album To the Sea in 2010, which drew favorable comparisons to the Beach Boys from critics. 

12. “Lost Sailor/Saint Of Circumstance” – The Grateful Dead 

The Grateful Dead unleashed their song about sailing, “Lost Sailor,” in 1980, well after the peak of their career that saw them dominate the psychedelic music scene of the late ’60s. 

It’s a sailing song that uses evocative, poetic lyrics to explore themes of loss and isolation, with a drifting boat serving as a metaphor for a listless life. 

The band released “Lost Sailor” on their eleventh studio album, Go to Heaven, their first release to feature Brent Mydland on keyboards. 

11. “Captain Kennedy” – Neil Young 

Like Bob Dylan, Neil Young has been closely associated with American folk music for many years, with his trademark guitar and vocal style. 

“Captain Kennedy” is a fine example of his singer-songwriter abilities, with Neil Young singing about his father’s experience on a wooden schooner at the height of the war. 

With its anti-war undercurrents and lyrical sensibilities, it’s another outstanding song from the Grammy Award-winning American singer. 

10. “Soul of a Sailor” – Kenny Chesney 

“Soul of a Sailor” is another example of how sailing songs can reflect the struggles and experiences of the brave people who venture into open waters. 

Kenny Chesney uses playful references to pirates, such as Blackbeard, in the song’s lyrics, showing great admiration for the sailing experience. 

It’s one of the best sailing songs from recent years, released in 2005 on the Kenny Chesney album Be as You Are (Songs from an Old Blue Chair). 

9. “Single-Handed Sailor” – Dire Straits 

The Dire Straits sailing song “Single-Handed Sailor” delivers upbeat rock in spades, featured on the 1979 critically acclaimed album Communiqué. 

The song title refers to Sir Francis Chichester, the first person to sail single-handedly around the world during the twentieth century. 

A high point in the discography of Dire Straits, “Single-Handed Sailor” is another powerful song about sailing worthy of any self-respecting playlist. 

8. “A Sailboat in the Moonlight” – Billie Holiday 

With her sweet and inimitable vocal style, Billie Holiday has all the qualities of a performer known for the best karaoke songs in the world. 

Her song “A Sailboat in the Moonlight” exemplifies what it is about her talent that so many people find appealing and why she’s enjoyed so much success. 

If your music taste includes smooth jazz with engaging lyrics and vocals, “A Sailboat in the Moonlight” by Billie Holiday is essential listening. 

7. “Wooden Ships” – Crosby, Stills & Nash 

We’re returning to Crosby, Stills, and Nash for another song about sailing, “Wooden Ships.” 

While this song was originally written in 1968, it took several decades to be recorded and released publicly. 

“Wooden Ships” was written in response to the Vietnam War, and it is a powerful piece of music that urges for peace in times of conflict. 

6. “A Pirate Looks at Forty” – Jimmy Buffett 

“A Pirate Looks at Forty” by Jimmy Buffett brings elements of rock and pop together, resulting in a superb song to listen to while sailing. 

Buffet’s moving vocals sing about the ocean’s call and how it relates to Earth as a timeless feature of the natural world. 

Jimmy Buffett worked with Alan Jackson on “It’s Five O’Clock Somewhere” several decades later—a great song about vacation that pairs well with “A Pirate Looks at Forty.” 

5. “Sail Away” – David Gray 

David Gray’s song “Sail Away” is another fine example of how sailing songs often draw on deep-rooted folk music influences in their approach to composition. 

For David Gray, the ocean and sailing are intimately tied to love and romance, with the song’s lyrics expressing his desire to escape on a boat with his lover. 

Released in 1998 on the David Gray album White Ladder, “Sail Away” was one of several singles featured from the long player, along with “This Year’s Love.” 

4. “Sloop John B” – The Beach Boys 

We’re back again with the Beach Boys, known for their beautiful songs about islands and catchy tunes focused on life on the oceans. 

“Sloop John B” was one of the standout tracks featured on their seminal album Pet Sounds and was a work of music that revolutionized rock and roll forever. 

Many decades later, “Sloop John B” would inspire Netflix’s television show Outer Banks, a popular teen drama series on the streaming platform. 

3. “I’m on a Boat” – The Lonely Island 

With a name like the Lonely Island, it’s perhaps not surprising that they’d take a stab at writing a sailing song, which resulted in the tune “I’m on a Boat.” 

This 2009 song features explicit lyrics that celebrate the more hedonistic aspects of life and was produced in conjunction with T-Pain. 

It’s an unusual entry in this playlist and one of the few rap songs about life on a sailboat, which was nominated for several prestigious music awards. 

2. “Sailor’s Lament” – Creedence Clearwater Revival 

Creedence Clearwater Revival released “Sailor’s Lament” in 1970 on their album Pendulum, a classic from their early discography. 

This song plays with the idea of drunken sailors and the morning after a night of heavy drinking, drilled in with repetitive lyrics. 

Creedence Clearwater Revival released many tracks and was inducted into the Rock and Roll Hall of Fame in 1993. 

1. “Sailing” – Rod Stewart 

One of the most popular mainstream singers of all time, Rod Stewart, has enjoyed many chart-topping hits on the Billboard Hot 100 Charts throughout his career. 

“Sailing” brings his distinct vocals and knack for catchy compositions together in style, a stadium anthem that urges his fans to sing along. 

Rod Stewart released “Sailing” on his 1975 album Atlantic Crossing, including the similarly themed song “Drifting.” 

Summary 

That’s a wrap on this playlist exploring sailing songs from some of the most prominent singer-songwriters and bands in the last few decades. 

It’s a topic that’s been prominent in the folk music scene but also explored in other genres, including jazz, rock, and mainstream pop music. 

Capturing the spirit of escape and adventure, these iconic songs are essential listening for anyone looking to get out on the ocean waves. 

What’s the best song about sailing, in your opinion? Leave a comment below.