23 Best Songs About Vacation

The best songs about vacations evoke the feeling of being away from the pressures of daily life where you are free to relax and have fun.

These upbeat and catchy tunes deliver exactly the kind of laid-back feelings that people expect when hitting the road for their next vacation.

Continue reading, and we’ll break down the details of these perfect songs for your next vacation to put you in a holiday mood.

The 23 Best Songs About Vacation

There are many great songs about vacations from over the decades, from classic rock songs to modern-day chart-topping pop hits.

We’ve ensured this playlist covers all genres and eras of music, so there’s something here that caters to all tastes.

Without further ado, here’s our playlist of the 23 best songs about vacation:

23. “Watermelon Sugar” – Harry Styles

We’re beginning this playlist that explores the best songs about vacations with a hit from Harry Styles, “Watermelon Sugar.”

Like the best songs about islands, “Watermelon Sugar” is full of rich and vibrant imagery of coastal waters on a relaxing vacation.

It’s the perfect song to put you in a holiday mood and was released with one of the most colorful music videos ever created.

22. “Two Tickets to Paradise” – Eddie Money

“Two Tickets to Paradise” by Eddie Money is another wonderfully upbeat song by one of the icons of the hard rock genre.

“I’m gonna take you on a trip so far from here,” the lyrics in this classic 1970s song sing, continuing, “I’ve got two tickets in my pocket, baby, we’ll disappear.”

Eddie Money released “Two Tickets to Paradise” on his self-titled album in 1977, which helped to define power pop.

21. “California Dreamin'” – The Mamas & The Papas

The Mamas and the Papas released “California Dreamin'” in the mid-1960s at the height of the hippy movement in the region.

It’s a catchy slice of folk rock and pop that has been widely played to this day and is regarded as a summer vacation anthem.

“California Dreamin'” has been featured in many movies, including on repeat throughout the Wong Kar-Wai classic Chungking Express.

20. “Island in the Sun” – Harry Belafonte

Classic crooner Harry Belafonte is no stranger to writing and performing hit songs, with several Grammy Award wins and nominations to his name.

“Island in the Sun” is one of his best songs, depicting a simple life living on a Caribbean island in the heat of summer.

Released in 1957, it’s a great song by Belafonte and was featured on the soundtrack to Islands in the Sun by Robert Rossen.

19. “Life Is A Highway” – Tom Cochrane

Country music singer Tom Cochrane released “Life is a Highway” in 1991 and received a nomination for Juno Single of the Year.

The lyrics explore themes of travel and adventure that capture the essence of setting out on a summer break with the family.

It’s another great vacation song that draws its inspiration from everyday life and a popular song from his discography.

18. “Holiday” – Madonna

Having released some of the best karaoke songs of all time, Madonna turned her attention to vacation songs with “Holiday.”

In this song, Madonna quite literally celebrates the idea of heading off on a vacation, wherever your destination might be.

Released in 1983, “Holiday” by Madonna cemented her growing reputation as one of the leading lights in the American pop music scene.

17. “On The Road Again” – Willie Nelson

Our number 17 pick returns once again to the country music genre with the classic track by Willie Nelson, “On the Road Again.”

“I just can’t wait to get on the road again; the life I love is makin’ music with my friends,” Nelson sings, “And I can’t wait to get on the road again.”

A hit song from his later period, Willie Nelson featured “On the Road Again” as part of the soundtrack to the movie Honeysuckle Rose, released in 1980.

16. “I’ve Been Everywhere” – Johnny Cash

Like Willie Nelson, Johnny Cash has produced some of the best songs of all time, with “I’ve Been Everywhere” a worthy addition to his discography.

Originally written by Geoff Mack, “I’ve Been Everywhere” sees Cash in fine form, exploring the daily life of a wanderer in search of a vacation destination.

It’s a classic country song that captures the spirit of a road trip into the wilderness and not knowing what to expect.

15. “It’s Five O’Clock Somewhere” – Alan Jackson and Jimmy Buffett

Our first entry into this list of songs about vacation time by Jimmy Buffett sees him collaborating with another musical icon, Alan Jackson.

“It’s Five O’Clock Somewhere” is a masterpiece of country and Western music and a popular reference to the catchphrase used to excuse early drinking.

The official music video was directed by Trey Fanjoy, with the singers lazing about on a luxury yacht as if on a permanent vacation.

14. “Soak Up The Sun” – Sheryl Crow

Sheryl Crow’s vacation song “Soak Up the Sun” is another wonderfully upbeat and catchy song that gets the listener in a holiday mood.

“I’m gonna tell everyone to lighten up. I’m gonna tell ’em that I’ve got no one to blame,” Sheryl Crow sings, “For every time I feel lame, I’m looking up, I’m gonna soak up the sun.”

Sheryl Crow received a Grammy Award nomination for Best Female Pop Vocal Performance for “Soak Up the Sun” in 2002.

13. “Toes” – Zac Brown Band

Having produced one of the best songs about wind, the Zac Brown Band turned their attention to vacation songs with “Toes.”

This unusually-titled song was released by the American country music band in 2009 and discusses the women and alcohol experienced by the narrator on vacation.

Released to positive reception, some critics likened the composition and vocal style to another great country singer, Jimmy Buffet.

12. “No Shoes, No Shirt, No Problems” – Kenny Chesney

Kenny Chesney took aim at vacation songs with “No Shoes, No Shirt, No Problems” in 2003.

Released on the album of the same name, this is another laid-back and smooth tune that’s a perfect song for summer vacations.

The lyrics bring up imagery of flip-flops and sand between your toes as you drink a cool and refreshing cocktail on a beach.

11. “School’s Out” – Alice Cooper

“School’s Out” made something of a resurgence at the turn of the 21st century when it was featured on the soundtrack to Dazed and Confused.

This classic rock song by Alice Cooper has long been an anthem for high school kids on the last day of school before breaking up for a vacation.

It’s a fun, exuberant song with the iconic vocals that helped Alice Cooper hit the Billboard Hot 100 charts on several occasions.

10. “Island In The Sun” – Weezer

Weezer’s “Island in the Sun” captures feeling free and relaxed on vacation with hugely optimistic lyrics from the narrator.

“On an island in the sun we’ll be playing and having fun,” the lyrics sing, continuing with, “And it makes me feel so fine I can’t control my brain.”

The American rock band Weezer has enjoyed a hugely successful career, taking influence from groups such as Metallica, Black Sabbath, and Blink-182.

9. “Margaritaville” – Jimmy Buffett

Our next trip through the discography of Jimmy Buffet is “Margaritaville,” which was released in 1977 on the album Changes in Latitudes, Changes in Altitudes.

It’s another song that blends imagery of summertime with drinking alcohol while lounging about in the Florida Keys.

Two years later, Jimmy Buffet would return to a related theme for his great song about sharks, “Fins.”

8. “Summertime” – DJ Jazzy Jeff & The Fresh Prince

The aptly-titled song “Summertime” from Jazzy Jeff and the Fresh Prince is another popular vacation song played by students.

Released in 1991, “Summertime” is a lively feel good song that won several awards on its initial release.

It helped to cement Will Smith’s popularity in the early 1990s and pave the way for his hugely successful career as a Hollywood star.

7. “I’m on Vacation” – Rhett & Link

Rhett & Link’s “I’m on Vacation” is one of the best vacation songs for holidaymakers and was released with a gorgeous official music video.

“We spent 14 hours on that sandcastle; everything is great (hey) ’cause I’m on vacation,” the song goes, “At least we’re not back at our jobs, which is at an ice cream sandwich factory.”

Anyone eager to escape their boring daily life and get away for a break will find that “I’m on Vacation” puts them in the right mood.

6. “Some Beach” – Blake Shelton

“Some Beach” is often considered to be among the best songs about the sea, which is fitting for the topic of vacation songs.

It’s another iconic country music song from a performer at the top of his game, with beautiful lyrics and guitar.

Released in 2004, Blake Shelton’s “Some Beach” was featured on his album Blake Shelton’s Barn and Grill, receiving acclaim from critics.

5. “Vacation” – Dirty Heads

The Dirty Heads’ song “Vacation” is an alternative indie rock song that also features a beautifully-directed official music video.

It’s another great song that evokes the feeling of the end of term and breaking up from school for a long summer vacation.

Dirty Heads released “Vacation” on their 2017 album Swim Team, with the song breaking out after going viral on TikTok.

4. “Holiday Road” – Lindsay Buckingham

Anyone familiar with the movie National Lampoon’s Vacation will be familiar with “Holiday Road” by Lindsay Buckingham.

This iconic track was the soundtrack to perhaps the most notoriously bad vacation in movie history, following the misadventures of the Griswald family.

Lindsay Buckingham released “Holiday Road” in 1983, which proved to be his most successful single to date.

3. “Vacation” – The Go-Go’s

Another great song about vacations from the early 1980s is “Vacation” by the Go-Go’s, which they released on the album of the same name.

“When you looked at me, I should have run, but I thought it was just for fun,” the lyrics sing, “I see I was wrong, and I’m not so strong, I should have known all along that time would tell.”

Here, the idea of going on a vacation is linked to a lovelorn feeling and desire to have a break from a relationship.

2. “Holiday” – Vampire Weekend

“Holiday” by Vampire Weekend brings us back to the best of indie pop and rock with a release that hit the charts in 2010.

It’s another fine tune that was accompanied by a colorful official music video that captures the vibrancy and fun of a vacation.

Vampire Weekend released “Holiday” on their album Contra, perhaps best known for the singles “Horchata” and “Cousins.”

1. “Kokomo” – The Beach Boys

Last but by no means least, we have “Kokomo” by the Beach Boys, adored by millions of fans for their warm and breezy coastal rock music.

Highly regarded for writing some of the best songs about California, the Beach Boys’ “Kokomo” is the quintessential song to listen to while on vacation.

One of the later releases by this iconic American rock band, “Kokomo,” found a huge audience thanks to its inclusion in the Tom Cruise movie, Cocktail, released in 1988.

Summary

We hope you’ve enjoyed these inspirational songs about vacation that capture the essence of taking a much-needed break from work.

With their beautiful melodies and lyrics that explore the visual splendor of lounging around by palm trees on a golden beach, these songs are a must for holidays.

Whether you’re dreaming of your next break or on the way to a tropical beach, these iconic songs are worth your time.

What do you think is the best song about vacation? Leave a comment below.