I have spent a lot of time in the islands. I’ve worked as a Scuba Instructor in the British Virgin Islands, St. Lucia, and the Turks & Caicos Islands. Additionally I’ve sailed the entire Windward Island chain on Wild Rose. Add to that a few other islands I’ve visited over the years and it’s safe to say I’ve spent my fair share of time in the islands.
Whether it’s hanging out in a bar, working on my boat or relaxing over an ice cold Hairoun or a Stag in the Southern Caribbean, I love listening to island music.
Now island music can vary wildly from person to person, there’s reggae, country, folk, classic rock etc. And everyone has a different version of what they think island music should be. Some island music is about sitting on a beach, and then there are sailing songs, and then just general tunes that make it easy to kick back on island time. Yes, island time is a real thing.
For my taste I like a lot of Marley, Buffett, Chesney and others because they’ve spent time in and mostly wrote their music in the islands. I think something about being there writing music gives more of a genuine island feel.
There are more than 130 songs on this list, for nearly nine hours of listening time. There is a link to the entire playlist at the bottom of this post.
Enjoy!
One Particular Harbour – Jimmy Buffett
Hemingway’s Whiskey (live) – Kenny Chesney
Coastal – Kenny Chesney
Sun Daze – Florida Georgia Line
Southern Cross (live) – Jimmy Buffett
As She’s Walking Away – Alan Jackson & Zac Brown Band
Day Drinking – Little Big Town
Knee Deep (feat. Jimmy Buffett) – Zac Brown Band, Jimmy Buffett
Some Beach – Blake Shelton
Friends – Animal Years
Sweet Annie – Zac Brown Band
Sunshine & Whiskey – Frankie Ballard
Sail Away – Lovd Ones & Leilani Woldfgramm
Settle Me Down – Zac Brown Band
Escape (The Pina Colada Song) – Rupert Holmes
Somewhere on a Beach – Dierks Bentley
Toes – Zac Brown Band
No Shoes, No Shirt, No Problems – Kenny Chesney
Guitars and Tiki Bars (live) – Kenny Chesney
Everybody Wants to Go to Heaven (with the Wailers) – Kenny Chesney, The Wailers
Down the Road (live with Mac McAnally) – Kenny Chesney, Mac McAnally
When I see This Bar (live with Eric Church) – Kenny Chesney, Eric Church
You and Tequila (live with Grace Potter) – Kenny Chesney, Grace Potter
Keep Me in Mind – Zac Brown Band
Beer in Mexico (live) – Kenny Chesney
On The Coast Of Somewhere Beautiful (live) – Kenny Chesney
Where the Boat Leaves From/ One Love (live) – Zac Brown Band
I Love This Life – LOCASH
Whatever It Is – Zac Brown Band
I’m Alive (with Dave Matthews) – Kenny Chesney, Dave Matthews
Boston (live) – Kenny Chesney
Follow Me – Uncle Kracker
Love For The Ocean (Tigerblood Jewel Remix) – Pastis, Tigerblood Jewel
Island Song – Zac Brown Band
When the Sun Goes Down – Kenny Chesney, Uncle Kracker
Boat Drinks – Jimmy Buffett
Rum is the Reason – Toby Keith
Mexico (2019 Remaster) – James Taylor
Two Pina Coladas – Brooks Jefferson
Three Little Birds – Bob Marley & The Wailers
Drink in my Hand – Eric Church
Margaritaville – Jimmy Buffett
Beer in Mexico – Kenny Chesney
Set Sail – The Movement
Hello (Reggae Cover) – Conkarah, Rosie Delmah
A Pirate Looks At Forty – Jack Johnson, Dave Matthews, Tim Reynolds
I’m In A Hurry (And Don’t Know Why) – Florida Georgia Line
I’m Yours – Jason Mraz
Coconut Tree (with Willie Nelson) – Kenny Chesney, Willie Nelson
Mexico (Live)– Jimmy Buffett
Son Of A Son Of A Sailor – Jimmy Buffett
Castaway – Zac Brown Band
Brown Eyed Girl – Jimmy Buffett
Volcano – Jimmy Buffett
Summertime – Kenny Chesney
Key’s in the Conch Shell – Kenny Chesney
The Life – Kenny Chesney
Bama Breeze – Jimmy Buffett
Key West Time – Jesse Rice
It’s Five O’Clock Somewhere – Alan Jackson, Jimmy Buffett
Jamaica Mistaica – Jimmy Buffett
Jolly Mon Sing – Jimmy Buffett
School Boy Heart – Jimmy Buffett
Only the Ocean – Jack Johnson
One Last Drink – Enter The Haggis
Three Little Birds – Bob Marley & The Wailers
Buffalo Soldier – Bob Marley & The Wailers
No Woman, No Cry (live at the Lyceum, London/1975) – Bob Marley & The Wailers
Redemption Song – Bob Marley & The Wailers
One Love/People Get Ready – Bob Marley & The Wailers
Somewher Over The Rainbow/What A Wonderful World – Israel Kamakawiwo’ole
The Weather Is Here, Wish You Were Beautiful – Jimmy Buffett
I Can See Clearly Now – Jimmy Cliff
Island State of Mind – Jesse Rice
Swimmin’ In Sunshine – Billy Currington
Somewhere in the Sun – Kenny Chesney
Good To Go To Mexico – Toby Keith
Island In The Sun – Weezer
Getting’ Down in a Pirate Town – Jesse Rice
Changes in Latitudes, Changes in Attitudes – Jimmy Buffet
The Seashores of Old Mexico – George Strait
Always Saturday Night – Thom Shepherd
Uncle John’s Band – Jimmy Buffet
Amarula Sun – Mac McAnally, Tim Montana
Come Away to Belize With Me – Jerry Jeff Walker
Pour Me a Vacation – The Great Divide
Sweet Kinda Summer – Jesse Rice
Leaving on a Jetplane – Slightly Stoopid
That Lucky Old Sun (Just Rolls Around Heaven All Day) – Kenny Chesney, Willie Nelson
Come Monday – Jimmy Buffett
Another Saturday Night – Jimmy and the Parrots
Go Away Cloud – Jesse Rice
Gulf Coast Girl – Caroline Jones, The Pelicanaires, Jimmy Buffett, Kenny Chesney, Lukas Nelson, Mac McAnally
Bare Feet – Caroline Jones
No Working During Drinkin’ Hours – Donny Brewer, Thom Shepherd
Saltwater Gospel – Fins Up Version – Eli Young Band, Jimmy Buffett
Waves – Phil Vassar
Another Day in Paradise – Southern Drawl Band
Trip Around the Sun – Kenny Chesney
One More Song About Mexico – El Camino
Spread the Love (Feat. The Wailers & Elan Atias) – Kenny Chesney, Elan Atias, The Wailers
Once In a Lifetime – Mac McAnally, Drake White
Duke’s On Sunday – Jimmy Buffett
Rock Me Like the Ocean – Wheeland Brothers
Love for Love City (with Ziggy Marley) – Kenny Chesney, Ziggy Marley
Lean on Me (Party Version) – Big Mountain, Dave Way
Island Style – John Cruz, Jack Johnson, Jackson Browne
Trip Around the Sun – Jimmy Buffett, Martina McBride
Ten Rounds With Jose Cuervo (Live) – Tracy Byrd
Trying to Reason With Hurricane Season – Kenny Chesney, Jimmy Buffett
Gulf Coast Breeze – Allison Clarke
Summertime Vibes – Lewis Brice
Pirate Song – Kenny Chesney
You and Islands – Zac Brown Band
The Sound of Sunshine Going Down – Michael Franti & Spearhead
Say Hey (I Love You) – Michael Franti & Spearhead, Cherine Tanya Anderson
(Sittin’ on) The Dock of the Bay – Smith & Myers
Salt and Lime – Clare Dunn
Water – Brad Paisley
Ghost Posting Letters – Peter Joseph Burtt and the Kingtide
Anyway – Entrain
Cool Down – Mishka
Dancin’, Shaggin’ on the Boulevard – Alabama
Worry B Gone – Willy Nelson & Kenny Chesney
Pirate Flag – Kenny Chesney
I Shall Return – Billy Currington
Good to Be Me – Uncle Kracker
Tides – Gone West
Margaritaville (Lost Verse) – Jimmy Buffett
Cabo San Lucas – Toby Keith
I’m always adding and tinkering to my Island Songs playlist, so if you have any ideas, drop me a line at sywildrose@jasonkoslow
Be Wild