It’s certainly not one of your happy-go-lucky sunshine in the afternoon sailing songs, but rather a song about the sea and what its dark underbelly can do to you. This is just one of those bands that captures the energy much better in the live environment.Īs the title suggests, “Lost Sailor” tells the story of a sailor lost at sea, experiencing the horrors of the ocean and finding himself at its mercy. As we know, the Grateful Dead are not exactly known for their studio cuts, but that doesn’t mean the songs don’t hold their own. “Lost Sailor” comes from the Dead’s 1980 album Go To Heaven, which was not well-received at the time of its release but has since held its own as one of their stronger studio records. Naturally the Grateful Dead have made their way onto my website again, this time on a list of sailing music. See a live video of the performance below. Jack & Dave make for a nice combination, and Tim Reynolds on guitar really solidifies this choice. “A Pirate Looks At Forty” is one of a few Jimmy Buffett songs that hasn’t been totally spoiled by my day job on the water, and the live rendition done by Jack Johnson & Dave Matthews from the Kokua Festival album is in my opinion even better than the original. I was hesitant to include any Jimmy Buffett songs on this list, because I’m honestly pretty tired of hearing Jimmy Buffet songs on boats these days, but I couldn’t bring myself to leave this one off. Jack Johnson, Dave Matthews & Tim Reynolds – “A Pirate Looks At Forty” (Jimmy Buffet Cover) That’s not how sailing works, remember?įind below our list of the 10 best songs about sailing and the sea. We’ve done our best to avoid those songs with this list, but we can’t promise that we stuck to our self-imposed rules very strictly. Some of this music, namely the stuff from the fun-loving easygoing side of things, has managed to become corny over the years due to being overplayed at beachside resorts everywhere. Many songwriters have touched upon the subject of sailing and the sea, both from the easygoing, fun-loving side, and from the dark, deceptive underbelly. Where there is peace, though, there is also the mighty strength of the sea that can bite back at you when you least expect it, throwing your boat and your life together into chaos. There’s something about sailing that can make one feel comfortable with everything happening in their lives and in the world, at least for a little while.
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