Sail-Inspired Songs: A Search for the Best Sailing Songs on the Planet

As a lover of all kinds of music and an aspiring musician, trying to increase my reperatoire of songs I can play on my guitar, I have often made searches for sailing or sailboat inspired songs. Many of the songs everybody knows, and others are ones you may not even think of as sailing or ocean songs until you listen closer to the words. Here are some of my favorite sailing songs.

Southern Cross: Crosby, Stills & nash

There is no mistaking this song as a sailing song. Crosby, Stills, & Nash write about sailing along the same passage I was on 2 years ago, sailing from Panama/Ecuador to Tahiti. When they sing this song I can see the Southern Cross in my mind and feel the warm breeze of the western tradewinds, pushing me towards the Marquesas. Brilliant song.

If I Had A Boat: by James Vincent McMorrow

Another song I found while searching for sailing or boat songs was one I had never heard of before, but have since come to love and played many times. I honestly found it accidentally, because I went to listen to Lyle Lovett’s, “If I Had A Boat,” which is completely different, and stumbled across this one. I immediately fell in love with the lyrics, music, and ideas of this song. With this artist’s unique voice and style, I’m sure you’ll love it like I do. I would love to hear your comments about this, especially if it’s the first time you’ve heard it.

Concerning Lyle Lovett’s song of the same name, I really couldn’t get behind him riding a pony on a boat, which is what he wants to do on his boat. LOL Feel free to listen to this song if you’re interested. It’s an enjoyable tune, just not my favorite lyrics.

Come Sail Away: Styx

Of course, being a teenager in the 80s, I couldn’t bypass this song, which I used to play and sing on the keyboard, but sometimes have the opportunity to play on guitar, with a willing crowd. This may be one of my most memorable songs of my life. It has two elements that appeal to me, sailing AND Science Fiction! Great song!

Brandy: Looking Glass

In my opinion, no collection of sailing songs wouldn’t be complete without this song. It’s a great song and a great story. Who doesn’t like this song? I remember listening to this song as a teenager and dreaming about the life of those sailors. I wasn’t really even into sailing at the time, but have come to it late in life. Of course, I’ve been looking for Brandy everywhere!

Sloop John B: Beach Boys

This is one of those songs I’ve been able to whistle along with, but all I remembered was the chorus about letting me go home, and didn’t even realize it was a song about a sailboat. It’s one I’ve rediscovered as I’ve sailed around the world.

I’ll Sail My Ship Alone: George Jones

This is one of those songs that have been cleverly-written by an old-timey country western legend. It’s not really about sailing, perse, but he uses sailing as a metaphor to talk about him and his girlfriend who apparently isn’t buying his committment or love or whatever. It’s a great song and easy to play on the guitar.

Sailing Away: Chris De BurgH

Here’s another classic from the 80s that talks about wanting to go sailing away with the boats that are going to all their destinations in the wide world. Great song. Fun to play on the guitar even if it’s less known.

Six Months in a Leaky Boat: Split Enz

This is such a great song. Definitely not what I would typically expect from this band, but it was enjoyable nonetheless. You can avoid all the intro by going to around 1:30 on the video.

Sailing: Christopher Cross

This is another song I enjoy playing and singing. He won 5 grammies the year this song was released. I can still remember listening to it in my brother’s apartment in Rialto. He’s apparently been singing and releasing albums ever since, but very few of them has been as big as the ones in the 80s.

Sailing to Philadelphia: Mark Knopfler and James Taylor

This is such a great song about sailing from the mother country to Philadelphia. It’s another one of those songs that tell a great story and you can almost feel yourself on that old ship, sailing along with the story tellers. I’m a huge fan of both of these guys.

I’m sure there will be more songs that come to my mind as soon as I hit the publish button, but those are the ones I’ll share for now. What sailing songs are your favorite? I am just planning on hearing from some Jimmy Buffet fans about their favorite songs of his, since he wrote so many of them. I suppose I should include at least one of his since he wrote so many. So here is the song I’ll include as a bonus:

Son of a Sailor: Jimmy Buffet

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