The Best Sailing Songs To Inspire Your Life On The Water

The Best Sailing Songs To Inspire Your Life On The Water

Planning to set sail can be tough. There are many things to prepare and check to ensure that you can have a fun and safe time while you’re out on the water.

Once that prep is done, however, and you’re out on the waves with the wind at your back, there is no feeling like it.

Choosing the right playlist can make that feeling even more special. Music can both soothe and excite us so whether you’re looking for a song to make you relaxed or make you want to take on the world, there is a sailing song for you. 

We’ve chosen a mix of different genres, moods, and artists to make a playlist of the best sailing songs to inspire your life on the water.

Some of these songs are directly about sailing and life on the water, whereas others use sailing as a metaphor for deeper aspects of life.

Whatever you’re looking for, you’re guaranteed to find the perfect sailing song for you.

Let’s get started. All of the songs are listed in alphabetical order, with the artist first.

1. Auli’i Cravalho – How Far I’ll Go

The artist name might not sound familiar, but if you’ve seen the Disney movie Moana, then you’ll undoubtedly recognize the song. Maybe starting off the list with a Disney song seems a little strange, but it’s a perfect sailing song.

Moana wants to escape her island life and take to the open seas to see what else is out there and this is the song she sings as she begins her journey. 

The lyrics are full of the joy of sailing and the potential it brings to Moana’s otherwise planned and boring life.

For example, “See the line where the sky meets the sea? / It calls me,” and “If the wind in my sail on the sea stays behind me / One day I’ll know / How far I’ll go.”

2. The Beach Boys – Sail On, Sailor

American rock band The Beach Boys have many songs that conjure up images of lazy days by the water and this is one of their best.

It’s a smooth mid-tempo song that features the vocals of guitarist Blondie Chaplin, instead of Brian Wilson, who was supposed to sing the song but decided to go surfing instead!

As the title suggests, the lyrics have plenty of nautical terminology and imagery throughout. “I sailed an ocean, unsettled ocean / Through restful waters and deep commotion.”

The theme of the song is perseverance through difficult times, something every sailor needs when they hit rough waters.

3. Bob Dylan – When The Ship Comes In

Bob Dylan is one of the greatest songwriters of all time so it’s no surprise to find that a sailing themed song of his makes the list. The song was written back in 1963 and included on the album ‘The Times They Are a-Changin’ but like most of Dylan’s songs, it’s timeless.

It’s an acoustic guitar led folk song that is perfect for relaxing on calm seas. It was allegedly inspired by a hotel clerk that saw Dylan’s unkempt look and refused him a hotel room.

The lyrics use the metaphor of sailing and the open sea to tell a story of being free and beaten by the oppressive “the man.”

4. Christopher Cross – Sailing

This song from Christopher Cross is so associated with sailing that it even is known by many as the song that kickstarted the genre “yacht rock.”

It was a massive hit for Cross as it not only hit the number one spot on the Billboard Hot 100 but also won Record of the Year and Song of the Year at the 1981 Grammy Awards.

The song is about Cross’ memories of sailing every summer. As a teenager, sailing with a friend helped him deal with the trials and tribulations of those years and no matter your age, that is a universal feeling. As Cross sings, “if the wind is right you can sail away / And find serenity.”

5. Crosby, Stills & Nash – Southern Cross

Crosby, Stills & Nash - Southern Cross

This legendary folk rock supergroup made of David Crosby, Stephen Stills, and Graham Nash have had immense success as both a group and individual artists.

As a group, they’re in the Rock and Roll Hall of Fame and Southern Cross was the final of their singles to chart in the Billboard Top 40.

Sailors have long used the constellation the Southern Cross for navigation when in the Southern hemisphere. It’s even reflected in the four stars that appear on the flags of Australia and New Zealand.

This is addressed in the song with the lyrics, “When you see the Southern Cross for the first time / You understand now why you came this way.”

6. Dire Straits – Single Handed Sailor

Dire Straits was a British rock band well known for combining rock guitars with influences from folk, country, and blues. “Single Handed Sailor” is the perfect song for sailing due to its relaxing vibe but also for the story behind the song.

It’s inspired by Sir Francis Chichester who, in 1966 to 1967, became the first person to single-handedly circumnavigate the globe, from west to east. You don’t need to be sailing solo around the world to enjoy the song but any sailor can become inspired by the story. 

7. Dolly Parton & Kenny Rogers – Islands In The Stream

Written by the Bee Gees, “Islands in the Stream” was released by country music superstars Dolly Parton and Kenny Rogers in 1983. It reached number one on the Billboard Hot 100 and also won the award for Favorite Country Single at the American Music Awards.

“Islands in the Stream” is a great song to listen to as the sun sets, especially if you’re sailing with someone special to you. The song uses the themes of sailing and water to make a beautiful love song.

For example, the lyrics of the chorus line include, “Islands in the stream / That is what we are,” and “Sail away with me / To another world.” 

8. Enya – Orinoco Flow (Sail Away)

Enya is one of the most unique artists of the last few decades and “Orinoco Flow” might be her most well-known song. The title refers to both the Orinoco Studios where the song was recorded and also the Orinoco river in South America. 

The main refrain of the song sees the words “sail away” repeated several times over. The lyrics to the verses read like an amazing trip around the world and are sure to spike the wanderlust of any sailor.

“​​From Bissau to Palau, in the shade of Avalon / We can sail, we can sail.” Who wouldn’t want to sail away to places like Fiji, Peru, and Bali?

9. Florence And The Machine – Ship To Wreck

This is one of the more modern songs that we’ve chosen. We like this song as it both fits the theme and adds something a little different to this list. Florence and the Machine are an English indie rock group and “Ship to Wreck” was released in 2015.

The song features a catchy chorus and the beautiful vocals of singer Florence Welch.

The meaning of the song has nothing to do with sailing itself but uses the idea of sailing and shipwrecks as a way to illustrate self-destruction. The lyrics ask the question, “DId I build a ship to wreck?”

10. Garth Brooks – The River

Garth Brooks is a country artist and is one of the most successful solo artists in American chart history. His career and success don’t really need any introduction as we’re sure you’ve heard several of his songs in the past, even if you don’t recognize this one. 

The first line of the lyrics explain the basic premise of the song as Brooks sings, “You know a dream is like a river.” In the case of this song, “The River” of the title are dreams that flow and never run dry. If you’re looking for an inspirational song, this is one of the best to choose.

11. Jimmy Buffett – Son Of A Son Of A Sailor

Jimmy Buffett - Son Of A Son Of A Sailor

Jimmy Buffet has many songs that have sailing themes but this is our favorite. It was released in 1978 and is one of the songs that Buffet almost always plays live at his concerts. It’s a gentle but touching song and is perfect for calm waters.

Buffet wrote the song about his grandfather, who was both a sailor and a great influence on Buffet’s life. The “Son of a Son of a Sailor,” in the title refers to Buffet himself.

There are many direct references to sailing throughout the song such as “Haul the sheet in as we ride on the wind,” and “Hear the bells ring as the tight rigging sings.”

12. Kenny Chesney – Soul Of A Sailor

Country singer Kenny Chesney likes to blend the traditional sounds of country music with the island sounds more commonly found in the Caribbean.

This has earned him the nickname of the “Caribbean cowboy” in many circles and the themes of his music and his lyrics reflect his love of beaches and water.

Like Jimmy Buffet (one of Chesney’s heroes) there were many songs we could have chosen but we opted for “Soul of a Sailor.”

The lyrics perfectly capture the freedom that many feel when they’re on the open seas with lines such as “When the wind fills my sail / Riding on a lifelong swell / Let my heart take me where it wants to go.”

13. The Looking Glass – Brandy (You’re A Fine Girl)

The Looking Glass is an American group famous for their pop-rock songs that became part of the Jersey Shore sound.

The band only released a couple of albums but their biggest hit was “Brandy (You’re a Fine Girl) ” which reached number one of the Billboard Hot 100 in 1972. 

The song is about a woman named Brandy who works as a barmaid in a busy seaport. She regularly flirts with the sailors who visit her bar but she pines for one sailor in particular.

Unfortunately for Brandy, this sailor decided that “my life, my lover, my lady is the sea.”

14. Otis Redding – (Sittin’ On) The Dock Of The Bay

No list of songs about sailing or life on the water would be complete with this song by Otis Redding. It’s a classic song and nothing on this list perfectly captures the feeling of relaxing on a dock or the deck of a sailboat and simply watching the world go by.

Unfortunately, Redding died shortly after finishing the recording of the song and it was the first single ever to posthumously top the charts.

There’s nothing better than sitting with your feet up and listening to this song. Consider listening to this song and “sittin’ on the dock of the bay / Watchin’ the tide roll away.”

15. Rod Stewart – Sailing

Although this recording by Rod Stewart is the most famous version of the song, it’s not the original. “Sailing” was originally recorded by the Sutherland Brothers in 1972, before Rod Stewart released it in 1975 and had an international hit with it. 

The song is a little more melancholy than many of the songs on this list.

The lyrics deal with separation and homesickness, but it’s still a great song to listen to as you sail. It’s easy to sing along to and is the perfect song to guide you home. “I am sailing / Home again /’Cross the sea.”

16. Van Morrison – Into The Mystic

The final song on our list comes from Northern Irish singer-songwriter Van Morrison. It was released in 1970 and fuses soft rock, blues, and jazz to make a mellow and relaxing song that is sure to be a sailing favorite. 

The song tells the story of a sailor who is out at sea and thinking about when he can return home to see his lover.

Although for most sailors the sound of a foghorn signals danger, in Van Morrison’s lyrics, they’re a sign that the sailor is getting closer to land. As the chorus line states, “When that fog horn blows / I will be coming home.”

Final Thoughts

In this article, we listed the best sailing songs to inspire your life on the water. We chose a variety of songs, new and old, happy and sad, so there’s sure to be a song to fit every mood.

Whether you’re an experienced sailor or a beginner, music can help bring some extra happiness and relaxation to your sailing days. So why not crank up the volume and listen to our choices as you set sail?