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Remember the Music and Help Create the All-Time Best Sailing Playlist

Last week we shared the news that David Crosby of Crosby, Stills and Nash had died. He was 81 years old. While the news has been circulating all over the internet, we’ve been intrigued and inspired by all the comments left by our readers. While some refer to their crossing of paths on the water, or in a boatyard or marina, many readers reflected on Crosby’s music that made their sailing years all the more memorable. Valerie Soper summed it up nicely when she wrote, “We, as Baby Boomers, are blessed to have this beautiful music bookend our journey from launch (of awareness) to the end of our voyage on the other shore.”

While we could sit here for hours writing an extended sailing eulogy for Crosby, that’s not the purpose of this post. Besides, the emotion and insight that you, our dear readers, have left on the page are far more interesting than any easy-to-find information we could dig up from the internet. Instead, we decided to use this as an opportunity to curate a sailing playlist. Not just any old playlist dreamed up by Spotify or Apple Music bots, but one that is made up of your personal favorite sailing songs. We can understand if your list is long, but in the interest of getting this done, we ask you to list only your top three — your all-time, most-listened-to, never-get-tired-of, top three sailing songs. (It’s pretty clear that Southern Cross will make the final cut.)

For those sailors who are usually happy to skip the music and just listen to the wind or the jabbering of the crew, here are a few songs you might like to consider.

(Sittin’ On) the Dock of the Bay – Otis Redding; Son of a Son of a Sailor – Jimmy Buffett; Sailing – Rod Stewart; Sailing – Christopher Cross. Here’s a cool version of Jimmy Buffett’s A Pirate Looks at Forty, performed by Jack Johnson, Dave Matthews and Tim Reynolds. We could add more, but we want to hear about your songs — no decade or genre is excluded.

One more thing about David Crosby. Apparently he did not write Southern Cross and had a limited involvement in its original recording. (You can look up the reasons why.) He did, however, write Wooden Ships, together with Paul Kanter of Jefferson Airplane, while aboard Mayan,

We leave you with this YouTube clip of Wooden Ships, which visually has nothing to do with the song, but, if you were at Woodstock, might bring back some memories… or not.

Drop your three favorite sailing songs into the comments below.


  1. Jack B. Chalais 2 months ago

    Orinoco Flo Enya/Celtic Women
    Cheeseburgers Jimmy Buffet
    Anything Buffet

  2. Carolyn Rosner 2 months ago

    I just have one to add: “Slip Away” (1989), a classic by the Pat Metheny Group. Pretty tune, and a wonderful tempo that just glides across the ocean on a beam reach. You can see the water sparkling as you listen to this one — especially Pat’s guitar solo.

  3. Adrian Blunt 2 months ago

    Check out their video in Oz.

    Wolverines, “A bloody great day to go sailing”

  4. David Bennett 2 months ago

    Cool change
    One particular harbor
    Believe it or not

    • Monica Grant 2 months ago

      David, is this ‘Cool Change’ by Little River Band?

    • David Bennett 2 months ago


    • David Bennett 2 months ago

      Absolutely yes it is such an awesome song

    • Monica Grant 2 months ago

      I agree. I’m surprised how many sailors in this thread know about Little River Band! My all time favorite of theirs is “It’s a Long Way There” — the original version, not Spotify’s edited version.

  5. Jim Immet 2 months ago

    Boat Drinks Jimmy Buffett
    The Captain & the Kid J Buffett
    Full Force Gale Van Morrison
    If I Had a Boat lyle Lovett
    Shadow Captain CSN
    To the Sea Jack Johnson
    Island Song Zac Brown
    Sailing to Philadelphia Mark knopfler
    Sloop John B Beach Boys
    Trawlermans Sing Mark Knopfler
    Pirate Callahan Divide
    Where the Boat Leaves From Zac Brown
    Salt Water Gospel Eli Young Band

  6. Chris Melhuish 2 months ago

    The Shadows – Wonderful Land

  7. Renee' G 2 months ago

    If I Had A Boat Lyle Lovett
    Boats to Build Jerry Jeff
    Sloop John B Beach Boys

  8. Craig Russell 2 months ago

    Here is a playlist I made about 10 years ago. It has all the classics and includes the theme song to Gilligan’s Island! Check it out.

    Or on the top right hand side of my sail blog:

    Southern Cross
    Into the Mystic
    Dock of the Bay Otis
    Sailing the Wind Loggins and Messina
    Harbor Jimmy Buffet
    Closer Grand Funk
    Sail Away Enya
    Talking at me Harry Nielson
    Sailing Shoes Little Feat
    Gilligan’s Island Theme Song
    SF Bay Blues Blues Image
    Montego Bay Bobby Bloom
    Back to the Island Leon Russell
    Sail on Sailor Beach Boys
    Sailing Christoper Cross

  9. Jack Christiansen 2 months ago

    Sailin’ Shoes – Little Feat
    Sail Away – David Gray
    Missed the Boat – Modest Mouse

  10. Mike Hockin 2 months ago

    Albatross by Peter Green and the original Fleetwood Mac. It’s not really about sailing per se but, Man…it sure sounds and feels like sailing.

  11. Craig Murk 2 months ago

    Single Handed Sailor -Dire Straits
    Closer to Home -Grand Funk RR
    Tales of Brave Ulysses -Cream

  12. Bob Lalanne 2 months ago

    Cecilio and Kapono – Sailing
    Jerry Jeff Walker – Sloop J B
    Harry Belafonte – Banana Boat
    Commodores – Sail On
    Jimmy Buffet – Son of a Son of a Sailor
    Looking Glass – Brandy
    Van Morrison – Into the Mystic & Moondance
    Loggins & Messina – Sailing the Wind

  13. Karen Kastel 2 months ago

    Everybody’s Talkin at me – Fred Neil

  14. Sheila Hubbard 2 months ago

    Six Months in a Leaky Boat – Split Enz

  15. Bill Willcox 2 months ago

    Gordon Lightfoot: Christian Island, High and Dry

  16. milly Biller 2 months ago

    The Dolphin song- Fred Neil
    Everybody’s talking – Fred Neil
    Son of a Sailor- Jimmy Buffet
    Southern Cross

  17. Marceline 2 months ago

    “No Fear” by Bay Area local Stephanie Teel

  18. Jan Passion 2 months ago

    Southern Cross
    Cool Change – Little River Band
    Dreamland – Third World
    Come Sail Away – Styx

  19. Marci Duys 2 months ago

    Anything Tracy Chapman was always a great listen on a delivery watch especially “I Used to Be a Sailor”

  20. Vince Casalaina 2 months ago

    It’s not directly a song about sailing, but for high intensity action – Danger Zone really fits.

  21. Bill L 2 months ago

    One Particular Harbor – Buffett
    Sailing – Christopher Cross
    Brandy You’re a Fine Girl – Looking Glass

  22. Carolyn Rosner 2 months ago

    Fisherman’s Blues, The Waterboys

  23. Kevin 2 months ago

    Moon River- Audrey Hepburn
    Lonely Looking Sky – Neil Diamond
    Wide River To Cross – Diana Krall

  24. Joe Siudzinski 2 months ago

    Cool Change – Little River Band
    Sail Away – Enya
    The Skye Boat Song

  25. Michael Quintus 2 months ago

    Life On A Boat – Gene Mitchell
    Knee Deep – Zac Brown Band (with Jimmy Buffett)
    Kokomo – The Beach Boys

  26. Kim Paternoster 2 months ago

    I’m surprised nobody mentioned Great Big Sea, one of the best Canadian bands ever. These boys are from Newfoundland, and they are celebrating their 30th anniversary of their start this year. They have mounds of VERY VERY cool sailing songs (when I discovered them, I stopped listening to Buffett).

    Excursion Around the Bay –
    The River Driver –
    Captain Kidd –
    I’m a Rover –
    Wave Over Wave –
    Lukey (with the Chieftains!) –
    Boston and St. Johns –

    And so so many more!!!

    David and I are flying to Vancouver in May to see one of the founders sing acoustic. I’ve been following them since I saw them open for Barenaked Ladies in Mountain View about 25 years ago… I cannot recommend these guys enough for sailing music.

    • Terry Wasik 2 months ago

      HI, I agree with you. Great Big Sea is a great group. When sailing they are a great group to listen to especially
      after we pass the rum bottle.

  27. Synthia Petroka 2 months ago

    Green Eyed Lady – Sugarloaf
    Salty Dog – Procol Harum
    Ride Captain Ride – Blues Image
    Sail Away – Randy Newman
    I’m on a Boat – The Lonely Island

  28. Ros de Vries 2 months ago

    G’day, this is Australia calling 🇦🇺

    Land Down Under – Men at Work (and anthem of the greatest sailing nation in the world!)
    Six Months in a Leaky Boat – Crowded House
    Waves – Miguel (Tame Impala remix)
    America’s Cup – Pond

    Meme bonus song: Sail – Awolnation

  29. Geoff Ferrell 2 months ago

    Lightfoot – Ghosts of Cape Horn, Marie Christine,

  30. Brad O’Toole 2 months ago

    Many of my favorites are already on the list but I have a new one for me:
    Sailboat – Kenny Chesney

  31. David Cohan 4 weeks ago

    Lee Shore, by David Crosby (seems essential given the original prompt)
    Lost Sailor, by Bob Weir & John Barlow

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