| Nothing But A Good Ride | Lyle Lovett | 4:28 | |
| There's a Beach Somewhere | Celeste Kellogg | 3:09 | |
| Gulf Coast Girl | Caroline Jones, The Pelicanaires, Jimmy Buffett, Kenny Chesney, Lukas Nelson, Mac McAnally | 3:45 | |
| Same Thing Happened to Me | John Prine | 3:18 | |
| Once In a Lifetime | Mac McAnally, Drake White | 3:04 | |
| Listen to a Country Song | Loggins & Messina | 2:47 | |
| Margarita Smile | Brent Burns | 3:40 | |
| Sailing Life | Eric Stone | 3:45 | |
| The Wedding Song (with Natalie Maines) - Duet with Natalie Maines | Charlie Robison, Natalie Maines | 4:28 | |
| Single Wide Dreamer | Aaron Raitiere | 3:32 | |
| Happy People | Hailey Whitters | 3:03 | |
| Living On Tulsa Time | Lee Conway with Moose Malone, Lee Conway, Moose Malone | 3:13 | |
| Shine On | Entrain | 5:42 | |
| Groovy Little Summer Song | James Otto | 3:37 | |
| When I'm Away From You | The Bellamy Brothers | 3:50 | |
| Conch Republic Song | Michael McCloud | 2:54 | |
| Duke's on Sunday | Henry Kapono | 5:18 | |
| Always Saturday Night | Thom Shepherd | 3:03 | |
| Laid Back and Key Wasted | Jim Morris | 4:11 | |
| Followed Her Around | Jimmy Rankin | 4:01 | |
| Island Time | Southern Drawl Band | 3:45 | |
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| Pour Me a Vacation | The Great Divide | 2:56 | |
| Stars in the City (feat. Little Big Town) | Old Dominion, Little Big Town | 3:19 | |
| Back Here Again | Jim Cuddy | 3:06 | |
| What Would Willie Do | Bruce Robison | 5:14 | |
| Give It Away | Bill Anderson | 3:19 | |
| Everybody Needs Their Beach | Kristian Bush, Dan Tyminski | 3:32 | |
| Five O'Clock World | Hal Ketchum | 3:04 | |
| More Time Drinking Beer | Southern Drawl Band | 3:14 | |
| I Take My Chances | Mary Chapin Carpenter | 3:45 | |
| Key Lime Pie | Kenny Chesney | 4:40 | |
| Tropical Vacation | Kelly Mcguire | 3:53 | |
| London Homesick Blues (Home With the Armadillo) | Gary P. Nunn | 6:03 | |
| The Big Bamboo | Jim Morris | 3:30 | |
| I Can't Spell Caribbean | Don Middlebrook, The Pearl Divers | 3:13 | |
| Mile Marker 24 | Howard Livingston & Mile Marker 24 | 4:09 | |
| Coconut Tree (with Willie Nelson) | Kenny Chesney, Willie Nelson | 3:24 | |
| Bye Bye | Phil Vassar | 3:17 | |
| My Town | Jeffrey Steele | 4:14 | |
| I Wasn't Gonna Drink Today (feat. Kevin Fowler) | Thom Shepherd, Kevin Fowler | 2:46 | |
| Changing Channels | Mac McAnally | 3:02 | |
| Smokey Mountain Rain | Ronnie Milsap | 4:27 | |
| I've Got Friends in Low Places | Elvis-Kingtinued | 3:30 | |
| I'd Give Anything | Blue Dogs | 3:13 | |
| No Worries | Gary Allan | 3:17 | |
| Down Home | Brothers Osborne | 3:38 | |
| Life's Too Short | Darius Rucker | 3:35 | |
| Boat Drinks | Jimmy Buffett | 2:40 | |
| Somewhere Nice Forever | Mac McAnally | 3:41 | |
