Meaning of “Sailing” by Christopher Cross

Sailing is a song performed by American singer and songwriter Christopher Cross. The lyrics of the song are about sailing and the beauty and liberation that come with it. According to Cross, he wrote the song about the fond memories he had while spending the summers of his teenage years sailing in Texas with a very close friend of his. Speaking with the famous American radio and television personality Howard Stern, Cross said of those sailing trips with his friend during his teenage years as trips that brought him total liberation. According to him, those sailing trips were very important to him since they provided him with some sort of escape from all the troubles of life.

You can view the lyrics, alternate interprations and sheet music for Christopher Cross's Sailing at Lyrics.org.

Sailing

Facts about the song “Sailing”

  • The song was written solely by Christopher Cross. According to Cross, the entire writing process of the song took about two years.
  • The song was produced by American singer-songwriter and music producer Michael Omartian, who also sang backing vocals on the song.
  • The song was released on 15th June, 1980 as a single from Cross’ debut album Christopher Cross – an album which won the Grammy Award for Album of the Year in 1981.
  • Sailing is one of the most famous songs in the yacht rock genre.
  • Sailing is the most successful song of Cross’ musical career. The song not only peaked at the number 1 spot on the U.S. Billboard Hot 100 but also won Cross as many as three Grammy Awards in 1981, including the Grammy Awards for Record of the Year and Song of the Year.
  • While accepting his Grammy for the song in 1981, Cross said that despite the song being his favorite on the entire album, it almost wasn’t released as a single.
  • Since its release in 1980, the song has been covered by several artists including Barry Manilow , N’Sync, and Avant.
  • Cross considers the song one of the best songs he has written throughout his entire career.
  • American rapper Sean Combs (also known as Puff Daddy or Diddy) sampled this song in his 1999 track titled Best Friends.

25 Responses

  1. Chris says:

    I loved this song from the very first note and syllable! Close your eyes and you can feel like you are sailing! Beautiful

  2. Ani says:

    It’s a song of passion- whether for sailing or dance or anything else
    An inspirational lifelong song
    Thank you!

  3. Jane says:

    It speaks of a freedom to me. Freedom to escape things in this life.

  4. Anonymous says:

    To me it’s a song for when the sun is setting. Not just for water but anywhere you can see it! Relax

  5. Anonymous says:

    It NEVER gets old, a timeless song that connects with your inner being, bringing you peace and escape. And the emotive vocals combined with the lyrics make it an unforgettable listening experience.

  6. Katherine Esquivel says:

    Just the best of the best. It’s sensitive inspiration gives so much peace to what it’s to overcome, for myself in love… it’s same time the music and his voice so romantic and gives hope in love contradicting freedom for humans. For me you find love in freedom … amazing Christopher Cross

  7. A Vietnam Veteran’s Daughter says:

    Beautiful song. I played this song at my father’s funeral last year. This is one of the songs he loved. I believe the reason why he liked this song so much was because it made him feel as if he was escaping from all his sufferings in search of freedom. He was a Vietnam Veteran who saw combat and ultimately suffered from PTSD and cancer linked to Agent Orange. I know my father is now sailing in Heaven enjoying peacefulness and freedom from all the years of pain and sufferings he endured from the war. I love you Tata… not one day nor one hour passes by that I don’t think of you! Miss you so much! RIP my hero! ❤️

  8. Anjan says:

    I’ve heard this song sooo many times (though sung by Rod Stewart).. and the song itself is so liberating. Thanks Chris for giving us this song.

  9. Joe says:

    I was 14yrs old in 1980 when I first heard this song “sailing”. I wanted to run away from home by boat. I had no idea how meaningful this song is, till this day this song moves me spiritually. Thank you CC, you are a great song writer. Now I hope to go on a shark cage adventure. Skydiving was awesome for my 40th birthday. Challenge your fears people.

  10. Michael S says:

    This may well be the most beautiful song ever.

  11. Anonymous says:

    This song came into my wife’s mind the day after our son died unexpectedly. Four months later, we read the lyrics. I believe his soul sent it to her. I will use it as the basis for my reading when his gravestone is placed above his ashes.

  12. Anonymous says:

    We are seeing Christopher this evening with the Nashville Symphony. The symphony will bring his beautiful songs to life!

  13. Anne says:

    The song of before will always be the greatest treasure rather than todays song. Even at my 28 I still choose the old songs that so inspirational. Wonderful and Beautiful…

  14. John Daubney says:

    THank you Chris. A band I am part of is presently working to perform this beautiful song. I have always loved it but in learning to play this song I have become more intimate with it and so I have been touched very deeply by the depth of the le beauty of the arrangement. Thank you Chris. I think we all, in our souls, long to rise above the challenges of everyday life and Sailing does just that.

  15. DoveSong says:

    One of my very favorite songs. Listened to it every time I was skiing. So liberating and hopeful of freedom. Today I will play it for my beloved brother who has passed on. We are releasing his ashes to the wind from his sailboat Liquid Sky. He left his kind loving good heart with all he touched and his sweet footprints on the
    earth. I miss him something awful. Thank you Chris!

  16. Paul Guthrie II says:

    I agree that this song never ever gets old, it can be taken in many ways, one can be our father in heaven, the other can be finding sobriety, another one can be God’s canvas to the beautiful scenery he produces, and the other can be talking to the one that you love, if they are doubting your love for them, ask if they’ll only believe in you, you could prove that your love is real and everlasting, either way, it gets me to cry sometime listening to it, but it’s very soothing, relaxing, and it makes me feel better personally, I would like to think Christopher Cross for singing that, I’m 54 and I’ve been listening to that song a long long time thanks Chris! 👍🏾🙏🏾💪🏾

  17. Miranda Young says:

    Timeless song that transcends. I was 6 years old when the song released and remember listening to it on the radio in mom’s red Mustang. I’ve often listened to this song though out my life and have shared it with both my sons and daughter. It’s beautiful.

  18. Bhanu murthy says:

    Truely inspiring lyrics of freedom and tranquility. Even after four decades after its release till date the instruments sound so fresh and authentic …

  19. Anonymous says:

    I am 79 yrs old and have always loved that song, it is truly a beautiful song written by a man who appears to be in tune with the lyrics of the song. Have listened to it through the years, never gets old or outdated, classic!

  20. Stephanie Unashamed says:

    Hello ~ My deepest gratitude for the grace in Chris Cross and to every soul that has posted here. Please know that you are being prayed for at this time. My so loved brother took me to a music store to help me buy my first stereo system. He brought the newly released vinyl album with us. I recall as I write here that the system he chose was SAE with a Technics strobe turntable. The music store was on the upper level of an open air mall. My brother played Sailing for me, for us. The mall and the entire store stopped and listened to the music, the lyrics. Allow me to borrow a quote ‘In the beginning, there is a movement. Made of tension and release, inspiration and serenity. From minor to major, one voice, then another, then a dozen more . . . soothing, moving, empowering. As profound as our memories, and as bright as our hopes. It’s at once a call and response. Crafted by inspiration, perpetuated through passion, it continues to resonate with every generation. It is as vital as breathing and as essential as moving. In many ways, it is the purest expression of life.’ This is the sound of living the Christian life. “Because God the Father so loved (your name here) that He gave His only Son so that if you believe in Him you will not be lost but have eternal life” John 3:16 So right where you sit, you can pray in the privacy of your own soul, ‘Father, I am believing in Your Son’ and you will be saved. I believe that Christopher Cross wrote Sailing over the period of two years out from the soul so that we could connect to the Creator. Divine Love changes everything by bringing us back to innocence again. It is here that, and I quote, “She’s a Mom protecting and training someone, something.” “I say something because she knows (she’s dealing with) an entity bigger than themselves. When Paul (her character’s son) starts going off, she begins losing power, and it puts her on an unpredicted journey to discover who we are in response to other people. That’s when we find ourselves again.” “I enjoy real stories and real people, but if I go back in history, whose story am I going to tell?” “That’s what I want to do,” she says, “but I don’t know where to find it.” ___ Rebecca Ferguson A book that grapples with messy humanity is found in the 66 books of the Word of God. Here we find ourselves again. All of humanity are objects of unconditional Love (John 3:16). Rather than objects of shame. May the day be calm ~ ~ ~

  21. Patrick says:

    This is a beautiful song. It can mean so much. This was the first song my wife and I danced to when we got married. It meant a lot to us while we were dating. We felt like we were sailing away together for a lifetime friendship!
    We are still married 43 years later.

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