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Sailing Songs: 25 Best Songs About Sailing

Who doesn’t want to sail off to the tropics and leave it all behind? If you’ve done it or ever hope to, then here is a Sailing Song playlist for the soundtrack to your adventure.

In the Trop Rock genre (think Jimmy Buffett to Kenny Chesney to Bertie Higgins) , there are many songs about sailing and songs that use sailing imagery. Explore more of these artists and you’ll probably discover even more sailing songs you’ll love.


Sailing Songs Playlist

Sailing Songs (Playlist)

In no particular order.

Sailing SongsThe Boat Drunks: “Hollow Man”
An escape song for those with the “3 mile stare” looking to leave a troubled life behind. “I want to ride on the wind just as far as I can.”
iTunes: Hollow Man
Amazon: Hollow Man

Sailing SongsJack Mosley: “Small Boats on Big Oceans”
Truly captures the modern sailor life “They dance to a rhythm that comes from the sea. They’re not too afraid to live out their dreams.”
Not Available on iTunes or Amazon
CD Baby: Small Boats on Big Oceans

trop rock songsHugo Duarte: “Back to the Islands”
A reminder of how good it is to dance on the sea. “The sea was made for sailing and I’m a sailing man”
iTunes : Back to the Islands
Amazon: Back to the Islands

Southern Drawl Band: “Gone with the Wind”
All about getting away to the islands. “Let’s sail away and save our troubles for another day.”
iTunes: Gone With the Wind
Amazon: Gone with the Wind

Sailing SongsScott Kirby: “Little Blue Boat”
Sweet love song about sailing away the one you love. One of the most popular songs by Kirby.
iTunes: Little Blue Boat
Amazon: Little Blue Boat

sailing songsEric Stone: “Whole 9 Yards”
Fun story about a divorce where she seemingly got it all, but he got the best part “the ocean near St. Barts” on his 27 foot sailboat.
iTunes: Whole 9 Yards
Amazon: Whole 9 Yards

Eric Stone: “Sailing Life”
“Sailing life is what I choose. Imported rum is my kind of booze.” That’s the life for sure!
iTunes: Sailing Life
Amazon: Sailing Life

Kelly McGuire: “Sailing Across the Gulf on My Own”
Funny but true! Sailing isn’t always glamours. Rain and squalls can make sailing feel like your “standing in the shower for 500 hours.”
iTunes: Sailing Across the Gulf on My Own
Amazon: Sailing Across the Gulf on My Own

Kelly McGuire: “Major Doubts About Water Spouts”
Sailboat racing from Texas to Mexico, spotting a water spout can make you wish you were back home.
iTunes: Major Doubts About Water Spouts
Amazon: Major Doubts About Water Spouts

Don Middlebrook: “Sailboat”
You don’t need a specific destination when you sail, “when I get there, that’s where I’m at.” It’s all about the journey.
iTunes: Sailboat
Amazon: Sailboat

Sunny Jim: “Sand Key”
Ever try to outrun a storm on a sailboat? It’s not easy. “We were running down wind with a double reefed main.”
iTunes: Sand Key
Amazon: Sand Key

Sailing SongsHannas Reef: “Sail Away”
All about escaping to the islands. “Hop on a boat and just sail away. Down to the tropics where people say, life is happy always.”
iTunes: Sail Away
Amazon: Sail Away

Sailing SongsHannas Reef: “Beer Drinkers and Sail Raisers”
A “Life is good” song where you can dream about the day you’re “bound for another port of call.”
iTunes: Beer Drinkers and Sail Raisers
Amazon: Beer Drinkers and Sail Raisers

Aaron Scherze: “Captain Jim”
An ode to a local Florida Captain who is now settled in the Clearwater area. “I wonder what you’ve seen, livin’ life on a breeze.”
iTunes: Captain Jim
Amazon: Captain Jim

Dennis McCaughey & Tropical Soul: “Caribbean Holiday”
Dream of sailing off around the world? “Leave behind our worries on a clear hot summer day.”
iTunes: Caribbean Holiday
Amazon: Caribbean Holiday

Sailing SongsParrot Island Band: “If I Just Sailed Away”
A little wishful thinking about sailing away from today. A good reminder that “time goes by fast.”
iTunes: If I Just Sailed Away
Amazon: If I Just Sailed Away

Howard Livingston: “This Boat”
If you’ve ever unfurled the sails on your own boat, you know it’s true: “this boat is going to change your life.”
iTunes: This Boat
Amazon: This Boat

Keith Sykes: “Sailor’s Prayer”
Sometimes the world isn’t just right, but getting out on sea where “the wind that blows so free” might help for a while.
iTunes: Sailor’s Prayer
Amazon: Sailor’s Prayer

Tim Charron: “Three Sheets to the Wind”
A Trop Country song with great beat. “Running from reality and never coming back again.” Sounds like the perfect plan.
iTunes: Three Sheets to the Wind
Amazon: Three Sheets to the Wind

Gene Mitchell: “Sail-ebration”
Spending the day on the ocean with good friends, food and drinks out on the sail boat. It’s definitely a “sail-ebration.”
iTunes: Sail-ebration
Amazon: Sail-ebration

Gene Mitchell: “Life on the Boat”
“It’s not a place for ordinary folk. It’s a special bread that feel the need to live their lives afloat.”
iTunes: Life on the Boat
Amazon: Life on the Boat

trop rock songsDennis Davis: “Sailing Again”
A day out on the bay with friends. “Sure feels good to be sailing again.” It always does when the breeze is just right.
iTunes: Sailing Again
Amazon: Sailing Again

Jim Morris: “Moonlight Sail”
So much fun can be had sailing in the night “drinking wine and raising hell.” This night seems to have it all.
iTunes: Moonlight Sail
Amazon: Moonlight Sail

trop-rock-songs-key-west-jim-morrisJim Morris: “The Sail Boat Race”
Sailing from a fun perspective, “you gotta love a sport that let’s you drink and use a word like wench”
iTunes: The Sailboat Race
Amazon: The Sailboat Race

Sailing SongsBrittany Kingery: “One with the Ocean”
A nautical ballad sailors will understand. “As the coast line is slipping away, you feel closer to home.”
iTunes: One With the Ocean
Amazon: One With the Ocean

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Rick Steffen

Saturday 3rd of June 2017

im disappointed my sailing song "Back on the Sea" wasn't picked.

Tammy Camp

Thursday 8th of June 2017

I hear that from many many artists regarding this playlist. After listening to almost 75 sailing songs in the Trop Rock genre, these are the ones I enjoyed the most.

John Bowman

Thursday 1st of June 2017

Check out "Sailing" by Sammy Hagar

Comments are closed.