21 Best Songs About Vacation For Holiday Moods

Most of us work way too much to have the time to go on vacation. If you haven’t taken one, you’ll probably have a hard time resting your mind after continuously working for so long.

Thankfully, there are plenty of songs about vacations to put you in a state of mind where you’re far from the cold commutes and concrete office buildings. While some songs have a deeper meaning, there are also some that simply are about having a good time and not working. Without further ado, here are the 21 best songs about vacation for holiday moods.

1. Vacation – The Go-Go’s

The Go-Go's - Vacation

Kathy Valentine wrote “Vacation” on a flight back to Los Angeles after visiting her hometown, where she developed a crush on a boy before leaving him behind. Before Valentine joined The Go-Go’s as their bass player and co-songwriter, she wrote a version of “Vacation” for her previous band, The Textones. After joining The Go-Go’s, the band tweaked the song and turned it into the well-known classic traveling song it is today.

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2. Kokomo – The Beach Boys

Although there is no actual “Kokomo” off the coast of the Florida keys, this song by The Beach Boys will make you want to go. The group lists places they would take their lover, ultimately settling on Kokomo. It’s here where you’ll fall in love as you take in the comfort of a sandy beach and a tropical drink in your hand.

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3. Holiday Road – Lindsey Buckingham

Lindsey Buckingham - Holiday Road (Official Music Video)

Lindsey Buckingham wrote this fun road-tripping song for the movie National Lampoon’s Vacation and in all of the sequels. Coming from a more in-depth songwriting background, Buckingham enjoyed creating the simple little ditty, showing a different side to his songwriting abilities.

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4. Margaritaville – Jimmy Buffett

“Margaritaville” is a vacation anthem most people have sung along to at some point in their lives. Inspiration for the song came to Jimmy Buffet after having his first margarita at a restaurant in Texas and wrapping up a tour with his group, The Coral Reefer Band. Afterward, he headed to Key West where he wrote the song. This highlights a laid-back lifestyle, where you can bury your woes in margaritas and easy-listening tunes.

5. Life is a Highway – Tom Cochrane

Tom Cochrane - Life Is A Highway (Official Video)

Another perfect road-tripping song, Tom Cochrane’s classic “Life Is A Highway” is an upbeat tune celebrating living life to its fullest. After returning from a trip to Africa, he was troubled after witnessing the hardships of the residents firsthand. He took the beginnings of a song he had laying around and used the emotion he had after his trip to finish writing the feel-good tune he needed to pull him out of that dark place. It sends a great message of pushing through hard times and enjoying life to the fullest.

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6. On the Road Again – Willie Nelson

Willie Nelson - On The Road Again (Official Audio)

“On The Road Again” is a classic, perfect for any road trip. Willie Nelson wrote this for the movie Honeysuckle Rose while on a plane with the movie’s director. In the song, he sings about his love for traveling to places he’s never gone and compares himself and his musician friends to a “band of gypsies.”

Next: Our playlist of great road trip songs

7. No Shoes, No Shirt, No Problems – Kenny Chesney

Kenny Chesney - No Shoes, No Shirt, No Problems (Official Video)

In this country hit, Kenny Chesney sings about wanting to get away from the overwhelming chaos of everyday life. Working his life away, he wants to trade the blue-collar life for bottomless drinks and bare feet on a sandy beach in Mexico.

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8. Island in the Sun – Harry Belafonte

Harry Belafonte - Island In the Sun (Official Audio)

Harry Belafonte wrote “Island In The Sun” for a movie he starred in of the same name. He performs the song in the movie, singing about a fictional island in the Caribbean called “Santa Marta” and his desire to live the island life forever.

9. Fly Away – Lenny Kravitz

Lenny Kravitz - Fly Away (Official Music Video)

Lenny Kravitz penned “Fly Away” while in the Bahamas, where he often resides throughout the year. With his mother being from the Bahamas, he visited the island quite often as a child.  Having been born in New York, he had experience with big city life and his more serene life back in the Bahamas. He sings about wanting to escape to a place far away, somewhere different than the norm.

10. Two Tickets to Paradise – Eddie Money

Two Tickets to Paradise (2022 Remaster)

“Two Tickets To Paradise” is the product of Eddie Money’s desire to skip town with his then-girlfriend. Her mother disapproved of him, doing everything to keep them apart. Money found inspiration to write the song while on a bus ride through the redwoods in Northern California. He said the “paradise” he sings about is a state of mind and not one place in particular.

11. Toes – Zac Brown Band

Zac Brown Band - Toes (Official Video)

“Toes” is a down-home, feel-good song about taking a break from life in the big city and enjoying the easy life by the beach. It comes to mind when your feet are soaked from walking through the snow when you’d rather have them in the sand down in Mexico and drinking all the fruity beverages you can handle.

12. Miami – Will Smith

Will Smith - Miami

In “Miami,” Will Smith details the luxurious lifestyle and bliss found on the south beach of Miami, Florida. This place is a melting pot of people from all backgrounds, all there to unwind and let loose. When it comes to vacation destinations, very few places can top Miami, and this upbeat tune encapsulates the city’s energy.

13. Coconut Tree – Shakira

Shakira - Coconut Tree (Audio)

In “Coconut Tree,” Shakira tells the story of how, early on in her and her lover’s relationship, they boarded a plane and headed to an island far from the peering eyes of the public. It’s a romantic song about how she fell more in love with him in their hidden paradise.

14. Coconut Tree – Kenny Chesney and Willie Nelson

Coconut Tree (with Willie Nelson)

Shakira isn’t the only one with a “Coconut Tree.” This laid-back vacation song paints a picture of sandy beaches, coconut trees, and relaxation for the listeners. Kenny Chesney and Willie Nelson sing about recharging their energy by hanging out high in the coconut trees, without a care in the world, and enjoying life by the beach.

15. La Isla Bonita – Madonna

Madonna - La Isla Bonita (Official Video)

In “La Isla Bonita” (which translates to The Beautiful Island), Madonna sings about longing to go back to a beautiful island she calls “San Pedro.” Some have speculated that the inspiration for the song is about a town in Belize. Although San Pedro is not an actual island itself, Madonna paints a blissful picture of the gorgeous Latin culture she experienced there.

16. Island Song – Zac Brown Band

Another tropical-themed Zac Brown Band tune, “Island Song” is all about unwinding, singing tunes, dancing, and enjoying copious amounts of adult beverages at the tiki bar by the ocean. Though not among their biggest hits, this is a staple for beachside bars across the country.

17. It’s Five O’Clock Somewhere – Alan Jackson and Jimmy Buffett

Alan Jackson, Jimmy Buffett - It's Five O' Clock Somewhere (Official HD Video)

“It’s Five O’Clock Somewhere” features our old friend Jimmy Buffet singing alongside Alan Jackson in a quitting time anthem. The pair sing about getting fed up with being overworked and pushed to their limit, so their “Jamaican vacation” starts right then and there with a tall drink to soothe their woes.

18. Soak Up the Sun – Sheryl Crow

Sheryl Crow - Soak Up The Sun

One of the quintessential feel-good songs, “Soak Up The Sun” was meant to cheer Sheryl Crow up following surgery. She was en route to Oregon when writing the song, and it became a massive hit. The song grabs at the feeling of wanting to leave the dreary winter months and head to a place where the sun shines bright and instantly improves your mental health.

19. Roam – The B-52’s

The B-52's - Roam (Official Music Video)

Though it’s been revealed in recent years by The B-52’s to actually be a song about death, “Roam” had already been established as one of those tunes where you visualize someone driving down the highway in a convertible. Technically, the song explains a spirit leaving the body and being free to roam, but we shouldn’t wait until we’ve passed to experience what the world has to offer.

20. California Dreamin’ – The Mamas and the Papas

California Dreamin'

When you think of vacation destinations in the United States, California (specifically, Southern California) immediately comes to mind. For those that live in the colder parts of the country, the fall and winter months can take a toll on you mentally. Because of that, a lot of people are “California Dreamin’” when the view outside of the window is dark and gray, especially if snow is involved.

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21. Holiday – Madonna

Sometimes, life can really drag you down in the worst way possible. Because of this, people need a reason to celebrate once in a while, no matter what they’re celebrating. Enter the hit song “Holiday,” where we learn that it would just be so nice if we all just took one day to break away from mundane tasks. Some of us could use more than just one day, though. Thank goodness for holidays, no matter what time of the year they may fall.

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