27 Songs About Vacations

“Club Tropicana” by Wham!

Song Year: 1983

How could anyone resist when George Michael sings about taking you to Club Tropicana with its free drinks and Wonderland-like atmosphere?

The song came from their debut album and became popular after their second album, Make It Big, hit #1 on the album charts and made them a breakout success. After their breakup in 1986, George Michael became a solo superstar.

“Hot Fun in the Summertime” by Sly and the Family Stone

Song Year: 1969

This short, punchy song sounds like it might be about a girl at first, but they refer to summer as “her.”

It's one of the simple songs about vacations that sings about the end of spring, the fun of a country fair, and school being out for the summer.

“Summertime, Summertime” by The Jamies

Song Year: 1958

The catchy chorus of this song is the repeated word, “summertime,” making this a great anthem for anyone who loves summer or takes a vacation in summer.

Its references to teachers, books, and studying make it the perfect song for getting out of school and not having to go back until the fall.

“On the Road Again” by Willie Nelson

Song Year: 1980

Willie Nelson started performing in the 1950s and became one of the most famous country music artists ever. He's had numerous hit songs, including this anthem for traveling and having a good time with friends.

Nelson wrote the Oscar-nominated song for the film Honeysuckle Rose. It became his ninth #1 country hit and one of his most famous songs. He won a Grammy for it, making it one of the ten he's won so far.

“Soak Up the Sun” by Sheryl Crow

Song Year: 2002

“Soak Up the Sun” isn't one of the songs about vacations that refers to going on a holiday. Instead, it encourages you to make the most of what you have. Many of Sheryl Crow's hits were about everyday life and trying to be happy despite difficulties.

The singer decides to soak up the sun, stop taking life too seriously, and make fun wherever she finds it. 

“Mexico” by James Taylor

Song Year: 1975

James Taylor sings about Mexico for several stanzas in what sounds like one of the easygoing songs about vacations south of the border. Then he says he's never been there.

The song was a Top 100 hit for Taylor. Carly Simon sang on the record, as did David Crosby and Graham Nash of Crosby, Stills, and Nash.

“Surfin' USA” by The Beach Boys

Song Year: 1963

“Surfin' USA” was one of the biggest early hits by the Beach Boys, all about spending time on the beach in the summer.

Anyone bound for a beach vacation or dreaming of the ocean can enjoy this song about everyone hitting the waves with their surfboards.

“Some Beach” by Blake Shelton

Song Year: 2004

With its title, a euphemism for a curse word, this song became a #1 country hit for Blake Shelton. He mentions listening to Jimmy Buffet's “Margaritaville” in his truck in the opening lines and suffers frustration with multiple other drivers.

Whenever someone angers him, he launches into the chorus about “some beach” waiting somewhere he could relax.

“Vacation” by Dirty Heads

Song Year: 2017

This tune by reggae-rockers Dirty Heads is one of the songs with vacations in the title that's less about a literal holiday than working a job you love so much that every day feels like one.

Part of the song's popularity was its fun video with Dennis Haskins, who played the school principal in the 1990s teen show Saved by the Bell, singing along to the song while bouncing around the halls of a school.

“Pontoon” by Little Big Town

Song Year: 2012

The song's about partying on a pontoon boat and enjoying the sun and river with friends. It originally started with a phrase containing a word that had to be changed to “hitch” to ensure it would get radio play.

“Pontoon” came from Little Big Town's fifth album and became their first #1 hit.