Best Songs About Vacations

Songs about hitting the road and relaxing can put you in the mood for a vacation, whether a planned retreat, a holiday vacation, or spontaneous time away from life’s obligations.

Enjoy these songs about vacations that take the listener away from the everyday grind for a precious few minutes.

“Vacation” by The Go-Go’s

Song Year: 1982

Despite the title, this song is about being unable to get over an ex-boyfriend. The upbeat music and the video, complete with the entire girl group water-skiing and having fun in the sun, make it a great vacation anthem.

In the video, the summer beach trip is just a fantasy, but that doesn’t make the song any less catchy and fun.

“Permanent Vacation” by Aerosmith

Song Year: 1987

Sometimes a short trip to a beautiful tropical paradise isn’t enough. This track is one of the best songs with vacations in the title. It’s about making a permanent move to a tourist hot spot.

The song mentions places like Montego Bay and St. Tropez. It also references being clean because some band members struggled with addiction.

“Margaritaville” by Jimmy Buffet

Song Year: 1977

This Jimmy Buffet classic is the anthem for people who want to kick back, relax, and have a good time. The opening notes of this song can bring a smile to people’s faces and make them wish they had a margarita in their hand.

“Margaritaville” is the perfect song for beach bums, those who want to be one, and people who crave a getaway from their lives for a little while.

“Summer Nights” by John Travolta and Olivia Newton-John from Grease

Song Year: 1978

The musical film Grease was a huge hit in 1978, in no small part thanks to John Travolta’s and Olivia Newton-John’s portrayals of Danny and Sandy.

The leather-jacketed, tough guy Danny and sweet good-girl Sandy meet and fall in love over summer vacation.

“School’s Out” by Alice Cooper

Song Year: 1972

For kids in school, summer vacation takes forever to come and goes by in a flash. This song became the anthem for kids in school everywhere and a favorite song to play as soon as spring term was over.

The track became shock-rock Alice Cooper’s first top-ten hit and remains one of his most well-known songs today.

“Holiday” by Madonna

Song Year: 1983

“Holiday” is one of the songs about vacations that’s about celebrating life and taking some time to enjoy it. The tune is about a literal break from your troubles and not a metaphor for something else, which makes it a great holiday anthem.

Madonna became the “Queen of Pop” and one of the most famous musical artists in the world. This song was the breakthrough hit in the US that started it all for her.

“Kokomo” by The Beach Boys

Song Year: 1988

The Beach Boys became famous in the 60s with multiple hits, like “Help Me Rhonda,” “In My Room,” and “I Get Around.” Over 20 years later, they released this song that became a #1 single and their last big hit.

The song lists all the wonderful places they’ll go, like Aruba, Montego Bay, and the fictional island of Kokomo near the Florida Keys. “Kokomo” is the perfect song for a vacation, a few hours spent at a beach, or time spent in a vacation state of mind.

“Holiday Road” by Lindsey Buckingham

Song Year: 1983

It’s hard to imagine a better road song than “Holiday Road.” This hit is one of the songs about holidays that doesn’t have many lyrics besides the title, but the chorus is so catchy that you don’t care.

The song became famous largely because it was in the film National Lampoon’s Vacation, a movie starring Chevy Chase that became a hit and a pop-culture phenomenon.

“Escape (The Piña Colada Song) by Rupert Holmes

Song Year: 1979

This song tells a sad story that turns happy about a man bored with his wife who answers a personal ad in the newspaper. The woman in the ad talks about piña coladas, beaches, and escaping to a fun-filled life.

When he answers the ad and meets the woman, it’s his wife, who’s also bored with their marriage, but this realization helps them discover each other again.

“Two Tickets to Paradise” by Eddie Money

Song Year: 1977

This tune is one of the songs about holidays that mention tickets, packing suitcases, and leaving for a vacation. It’s a fun song to take literally, whether about an actual jet-setting vacation or the end of the work week.

Most people think the song is about convincing a woman to have sex with him for the first time. This interpretation doesn’t stop it from being a great vacation anthem, especially for couples.

“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

"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.

“No Shoes, No Shirt, No Problems” by Kenny Chesney

Song Year: 2003

This song about taking time off a difficult job and spending time barefoot and shirtless on a Mexican beach is a wish many people share.

The relatable lyrics and Chesney’s smooth voice helped the song hit #2 on the country chart.

“Toes” by The Zac Brown Band

Song Year: 2006

“Toes” is another of the many songs about vacations on a beach. The singer is on a beach, enjoying the sunshine. It gets its name from his toes soaking in the sea while he’s sitting on the sand.

The song ends with him back at home, sitting in his yard with the same attitude and enjoying life.

“Vacation” by Thomas Rhett

Song Year: 2015

Among the songs with vacations in the title, this track is one of the most lighthearted. It’s not about a breakup or wishing for time off but having a good time.

The song shows you it’s possible to be on vacation and have fun at home or on a tropical beach.

“Blame It on Mexico” by George Strait

Song Year: 1981

“Blame It on Mexico” is about a man in a Mexican bar to get away from it all who meets a woman, falls in love, and gets his heart broken.

He blames his bad luck on Mexico, the music, and drinking too much good Mexican tequila.

“Long Hot Summer” by Keith Urban

Song Year: 2010

Keith Urban sings about wishing he was with the girl he loves on a road trip and enjoying the lazy summer days in “Long Hot Summer.”

Urban wrote the song with pop star Richard Marx, and it became one of his #1 hits on the country song chart.

“Katmandu” by Bob Seger and the Silver Bullet Band

Song Year: 1975

This rock song is one of Bob Seger’s most well-known hits and one of his most fun. He sings about wanting to escape his life for a while by heading to “Katmandu” and taking it easy.

Kathmandu, Nepal, is the home of Buddhism and one of its biggest centers worldwide, making it a great place to escape the hustle and bustle and contemplate life for a while. 

“Come Away With Me” by Nora Jones

Song Year: 2002

In this jazzy, soulful song, Nora Jones urges someone to come away with her. She mentions a bus, a mountaintop, fields, and a tin roof, showing wherever they go will be fine.

This song is perfect for the idea of running away from life’s stresses and how being anywhere with someone you love can be a vacation.

Top Songs About Going On Vacation, Final Thoughts

Some of these songs about vacations are about beaches and traveling. Many more are about summer vacations for students who are done with tests and studying for a few months.

A few songs are metaphors for enjoyable activities instead of literal vacation time.

The tunes are all fun to listen to whether you’re on vacation or dreaming of one. We hope you enjoyed these songs about holidays.

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