Top Sailing Songs

The American Sailing Association is a venerable organization that I belong to as a professional mariner. I hold ASA credentials to teach three certified courses. Having said that, the ASA list is flawed for lacking “Sailing,” by Christopher Cross. It is the single-most mentioned song by guests at Let’s Go Sail, followed by another one that doesn’t bear repeating. But in fairness, ASA stipulates these as classic rock ‘n’ roll, so they still constitute top sailing songs.

“Sailing” broke in 1980 and became an instant hit for the fantasy: “Sailing takes me away to where I’ve always  heard it could be / just a dream and the wind to carry me / And soon I will be free.” Everything about the song is evocative, shimmery, escapist, lyrical, beautiful–and correct. Those who go sailing for the first time remark afterward that it was just like Christopher Cross said.

VH1 named it the “greatest soft-sational song of all time,” which is silly but probably true. Many artists have covered the song, and it plays in a continuous loop at Disneyland and Disney World. From the viewpoint of social media, the song shows up quite high in google searches for the word sailing. Storybase.com refers to it in three of its top ten searches for terms such as “who sang Sailing?”

Well, it’s not far down to paradise, at least it’s not for me
And if the wind is right you can sail away and find tranquility
Oh, the canvas can do miracles, just you wait and see.
Believe me.

It’s not far to never-never land, no reason to pretend
And if the wind is right you can find the joy of innocence again
Oh, the canvas can do miracles, just you wait and see.
Believe me.

Sailing takes me away to where I’ve always heard it could be
Just a dream and the wind to carry me
And soon I will be free

Fantasy, it gets the best of me
When I’m sailing
All caught up in the reverie, every word is a symphony
Won’t you believe me?

Sailing takes me away to where I’ve always heard it could be
Just a dream and the wind to carry me
And soon I will be free

Well it’s not far back to sanity, at least it’s not for me
And if the wind is right you can sail away and find serenity
Oh, the canvas can do miracles, just you wait and see.
Believe me.

Sailing takes me away to where I’ve always heard it could be
Just a dream and the wind to carry me
And soon I will be free

Meanwhile, the list of seven rock songs epitomizes a strange anomaly about sailing. For all its glamour, the sport has produced few memorable songs. The only other one that people on my boat recall is the theme from “Gilligan’s Island,” a despicably stupid sit-com that lasted only two seasons until it was catapulted into perpetual syndication.

At Let’s Go Sail, we play a list of popular songs embracing sailing, boating, weather, beaches and water. Sometimes the connection is buried in the lyrics, which makes it fun to find. You wouldn’t think “Tender is the Night” by Tony Bennett would have any connection, but it does.

Should tomorrow find us disenchanted
We have shared the love that few have known
Summers by the sea, a sailboat in Capri
These memories shall be our very own

Summer Wind, Frank Sinatra

Hero, Mariah Carey

Blowin’ in the Wind, Bob Dylan

Wind Beneath My Wings, Bette Midler

Summer Breeze, Seals and Croft

Stormy Weather, Tony Bennett

On a Clear Day, Tony Bennet

Beyond the Sea, Bobby Darin

When the Wind Was Green, Frank Sinatra

Calypso, John Denver

River, Joni Mitchell

Ol’ Man River, Frank Sinatra

Here Comes the Sun, Beatles

Take Me Home, Phil Collins

I Left My Heart, Toni Bennett

Sailin’ the Wind, Loggins @ Messina

Islands in the Stream, Dolly Parton & Kenny Rogers

Mandolin Rain, Bruce Hornsby & The Range

Somewhere Over the Rainbow, Michael Bolton

You Are the Sunshine of My Life, Stevie Wonder

The River Runs Low, Bruce Hornsby & The Range

Follow You, Follow Me, Genesis

The Shadow of Your Smile, Tony Bennett

Rhythm of the Rain, The Cascades

Crying in the Rain, Everly Brothers

A Summer Song, Chad & Jeremy

Windy, The Association

And When I Die, Blood Sweat & Tears

Sloop John B, Beach Boys

Catch the Wind, Donovan

Have You Ever Seen the Rain, Creedence Clearwater Revival

Wooden Ships, Crosby Stills & Nash

Everybody’s Talkin’, Harry Nilsson

Elusive Butteryfly, Bob Lind

Stranger on the Shore, Acker Bilk

Windmills of Your Mind, Dusty Springfield

Blue Bayou, Roy Orbison

Ebb Tide, The Righteous Brothers

Summer Rain, Johnny Rivers

Sailor, Petula Clark

Come on Down to My Boat, Every Mother’s Son

The Captain of Her Heart, Double

Sailing to Philadelphia, Mark Knopfler

Suddenly It’s Spring, Stan Getz

Bridge Over Troubled Waters, Simon & Garfunkel

Here’s That Rainy Day, Gene Ammons

Ironically, half the ASA playlist doesn’t show up here. I’ve not heard the Jimmy Buffet song, either. We once owned a Catalina 25 named Incommunicado, which I thought for the longest time was just a misspelling of incommunicada. But no, it’s a Jimmy Buffet song. I still haven’t heard it. You can imagine the trouble we had communicating with the Coast Guard on radio with that name. It sounded like we were mocking them. 

Movies about sailing are often disappointing, but that’s another blog.

Let’s Go with Top Sailing Songs

Check rates and pick a day for a sailboat charter. See reviews on Trip Advisor from sailors just like you.