4 Country Songs From the 1990s and 2000s That Sound Like Taking a Vacation

As we enter the summer season, so do our playlists. Here are a few country songs (from the late 90s and early 2000s) that remind us what it feels like to take a vacation, even when we’re just sitting at home on the couch.

“Guitars and Tiki Bars” by Kenny Chesney

When Kenny Chesney needs a break from real life, there are a couple of things he likes to do. He’s probably either grabbing his guitar or relaxing on the beach with a drink in hand.

To guitars, tiki bars and a whole lotta love
Mangoes and Marley, you know, fit me like a glove
Sixth gear with nowhere to steer
When enough is enough
It’s guitars, tiki bars, and a whole lotta love.

This song just sounds like a good time, which is why it’s the perfect addition for your beach trip playlist.

“Blue Clear Sky” by George Strait

This song is about how love finds you out of nowhere.

As writer Bob Dipiero explained to The Boot, the song’s title was actually inspired by a line from Forrest Gump. Initially, Strait was confused by the line being “blue clear” instead of “clear blue,” but ended up growing fond of the lyrical mix-up.

“In the movie, Forrest talks about, ‘Life is like a box of chocolates.’ And also, he was talking about his girlfriend, Jenny, and how she would come and go out of his life. At one point, he says, ‘And out of the blue clear sky, Jenny came back.’ And I was listening, thinking, ‘Hey! It’s clear blue sky, it’s not blue clear sky!’ Just that little turn of phrase stuck in my head.”

“It’s Five O’Clock Somewhere” by Alan Jackson and Jimmy Buffett

It would have felt illegal to make a list like this and not include this classic drinking anthem. Especially if you’re looking forward to an escape from the mundanities of everyday life, “It’s Five O’Clock Somewhere” is the song for you. In the chorus, Jackson and Buffett sing about being ready to get the party started no matter what time of day it is.

Pour me somethin’ tall and strong
Make it a Hurricane before I go insane
It’s only half-past twelve, but I don’t care
It’s five o’clock somewhere.

“Heads Carolina, Tails Claifornia” by Jo Dee Messina

It might be one of her biggest claims to fame now, but “Heads Carolina, Tails California” was actually a last-minute addition to Messina’s debut self-titled project. This song is about travel, so the subject matter is right on the money. But what’s more is that it’s about being happy no matter where you are, because you’re with the one you love. That’s the kind of vacation we all need.

Photo by: Beth Gwinn/Redferns