25 Of The Best Songs About Vacations And Holidays

Written by Dan Farrant
Last updated

The importance of going on a vacation cannot be emphasized enough. It provides us periods of respite and a chance to step away from the daily hustle and bustle.

In addition, vacations free us from our routines — albeit temporarily — and allow us to rest and rejuvenate. Whether it’s an adventurous trip to a distant land or a quiet retreat in the countryside, vacations promise a change of scenery and treasured memories.

So pause, reflect, and reconnect for a moment as we present to you 25 of the best songs about vacations and holidays. Enjoy reading!

1. “Vacation” By The Go-Go’s

Let’s start the list with a song with “vacation” in the title. The all-female rock band The Go-Go‘s released “Vacation” in 1982 as a single from their album of the same name.

The lyrics paint a picture of a summer romance where the narrator meets a guy during her vacation. He’s supposed to be a fling, thinking it’s all about fun and games. But after going their separate ways, the narrator wishes she had stayed to see more of him.

In the following days, she can’t stop thinking about him. In fact, she thinks she’s going to forget him after a week. But two weeks later, she still hasn’t gotten over him. It’s at this point she realizes that she’s in love.

2. “Margaritaville” By Jimmy Buffett

On the surface, Jimmy Buffett‘s “Margaritaville” epitomizes the laid-back, carefree vacation vibe. It’s about a man enjoying a leisurely time in a tropical paradise, sipping margaritas and basking in the sun. But there’s more to it than meets the eye.

Released in 1977, the song quickly became an anthem for people seeking escape from the daily grind. However, the song chronicles the narrator’s gradual recognition that it was his fault that destroyed his chance with a woman he loved.

At first, he thinks that “it’s nobody’s fault.” Later on, he plays with the idea that “it could be my fault.” Finally, at the end of the song, he recognizes, “it’s my own damn fault.” He comes to that conclusion while wallowing in alcohol.

3. “Vacation” By Dirty Heads

Our next song is a unique take on the concept of vacation. The American reggae rock band Dirty Heads released “Vacation” in 2017 from the Swim Team album.

Thematically, this song with “vacation” in the lyrics explores the idea of loving what you do so much that it feels like being on vacation every day. The narrator recognizes the downside of every job, but the difference between him and others is the right mindset.

The narrator further encourages listeners to change their lives if they’re unhappy with their situation. He urges them to stop waiting for the weekend or a vacation to enjoy life. Instead, he tells us to find something we love doing so that every day feels like a vacation.

4. “Island In The Sun” By Weezer

When life becomes overwhelming, it’s the perfect time to find an idyllic escape where one can relax and let go of all worries. “Island in the Sun” by Weezer encapsulates this idea of a perfect vacation.

The lyrics describe a paradise getaway on an island where one can bask in the sun and appreciate the beauty of nature. It depicts a sense of freedom and tranquility that one often associates with a vacation.

In the song, this getaway serves as an escape from reality, where the narrator can rest and not think about problems and worries. The cherry on top is him being with his loved one and them enjoying each other’s company.

5. “Holiday” By Madonna

Holidays are the same as vacations in that both mean taking a break from the usual routine and stresses in life. However, Madonna‘s “Holiday” goes beyond the traditional idea of a vacation.

The song doesn’t specify the location or destination for the holiday. What it does is emphasize the emotional and psychological break one needs from routines and responsibilities. This aligns with the concept of a vacation during which one can rest and rejuvenate.

In addition, “Holiday” talks about the universal feeling of needing a break from regular life. It suggests a metaphorical holiday — a time of joy, unity, and celebration.

6. “Some Beach” By Blake Shelton

Life is all about ups and downs, though sometimes it’s more of the latter. However, it is up to us how we deal with the difficulties. This is the message conveyed in Blake Shelton‘s country song “Some Beach.”

The song is a humorous story of a man facing various annoyances in his daily life. We’re talking about traffic jams and dental visits. In each situation, he dreams of being on “some beach, somewhere,” a place where he can relax and not worry about the stressors of his daily life.

When you listen to the song for the first time, it may seem like a song about escapism. But the song is a reminder for us to find joy and gratitude even in the midst of difficult situations.

7. “Toes” By Zac Brown Band

Going to a beach for a vacation is a tempting idea. That’s why the narrator in Zac Brown Band‘s “Toes” gives in and enjoys life by the beach with no worries.

The narrator is depicted with his toes in the water, sitting in the sand, and holding a cold beer. It’s a quintessential image of relaxation and leisure — a perfect beach vacation. The lyrics convey a sense of carefree enjoyment and appreciation for this simple pleasure.

However, the song concludes with the narrator returning home. Nevertheless, he continues to appreciate his life, saying, “Life is good today.”

8. “No Shoes, No Shirt, No Problems” By Kenny Chesney

You cannot blame someone for going on a much-needed beach getaway after “working six days a week” for a while. Take it from Kenny Chesney‘s “No Shoes, No Shirt, No Problems.”

In the song, the narrator sings about the joys of being somewhere where there are “no shoes, no shirt, and no problems.” This phrase suggests a location where societal expectations are relaxed. The primary focus is on relaxation and enjoyment.

In essence, the song is about leaving behind the stresses of everyday life. It’s not wrong to trade daily stressors for the simple pleasures of sun, sand, and sea.

9. “Surfin’ U.S.A.” By The Beach Boys

Up next is the 1963 single “Surfin’ U.S.A.” by the rock band The Beach Boys. This song celebrates the surfing culture of the US, particularly in California. It captures the essence of a surfing vacation, idealizing the lifestyle associated with it.

The lyrics list various surfing spots across the US, from California to the Eastern Coast. This paints a picture of a grand surfing road trip, making the song a tribute to these popular vacation spots for surfers and non-surfers alike.

In the context of a vacation, the song conveys the joy of escaping the mundane and embracing adventure. Hence, the song is not just about surfing. It’s also about the ideal vacation, characterized by freedom and appreciation for the American coastal landscape.

10. “Pontoon” By Little Big Town

One of the perfect summer songs is Little Big Town‘s “Pontoon.” At its core, it’s all about having a relaxing and fun-filled time on a pontoon, a flat boat that relies on pontoons to float.

In the lyrics, the pontoon boat is depicted as a place for leisure and relaxation. It’s the perfect place for a party, enjoying a drink, having a barbeque, and hanging out with friends.

The song also reflects the joy of summer days, the freedom of being out in the water, and the camaraderie that comes from sharing such moments with friends. The vibe of this song is carefree and laid-back, much like an ideal vacation.

11. “I’m On Vacation” By Rhett And Link

The humorous and catchy song “I’m on Vacation” by Rhett and Link is about the determination to enjoy a vacation, no matter what. It portrays a strong sense of escapism, where the narrators refuse to let difficulties ruin their vacation.

In the lyrics, the narrators are determined to make the most of their vacation. It’s filled with surfing, enjoying the beach, and worrying about nothing. They declare, “Everything is great, ’cause I’m on vacation.”

The narrators share the importance of maintaining a positive attitude even if things don’t go as planned. Their vacation is still way better than their jobs at an ice cream sandwich factory.

12. “Summertime, Summertime” By The Jamies

The upbeat song “Summertime, Summertime” by The Jamies captures the joy and freedom that come with the summer vacation period. It’s an anthem for the end of the school year and the start of summer.

In relation to vacation, the song reflects the excitement and anticipation of having fun. The narrator plans on swimming every day and dancing every night. And if people complain that they’re not working, they can just say, “It’s summertime.”

In essence, the song is about enjoying summer, when days are filled with sun, leisure, and adventure. It’s about looking forward to the thrill and happiness of summer vacations filled with fun activities.

13. “Hot Fun In The Summertime” By Sly And The Family Stone

Up next, we have a number from the American band Sly and the Family Stone. Released in 1969, “Hot Fun in the Summertime” celebrates the joy and relaxation of the sunny season. And we know that when it’s summertime, it means vacation!

The song highlights the simple pleasures of being outdoors in the sun or going to the beach. Listening to music and spending quality time with friends and family are also activities that people look forward to.

The lyrics mention the end of spring and the return of summer days, indicating a transition into a period of fun and leisure. The song also conveys nostalgia for these enjoyable summer days.

14. “Vacation” By Thomas Rhett

Whether you’re on a real vacation or sitting in traffic, listening to “Vacation” by Thomas Rhett is the thing to do. This energetic anthem is all about taking a break from routine and enjoying life to the fullest.

The song was inspired by a trip that Rhett and his wife took to Hawaii. The lyrics reflect their excitement as they have not taken a vacation in years. The song shows how necessary it is to step away from everyday stresses and immerse oneself in the pleasures of a vacation.

The song’s premise is essentially about partying and living as if you’re always on vacation. It promotes the idea of making every moment count, just like you would on a vacation.

15. “Two Tickets To Paradise” By Eddie Money

Don’t we all look forward to having a vacation to get away from the stressors of life? Eddie Money just has the right idea: he’s got “Two Tickets to Paradise.”

Here, the song suggests a longing to take a break and go somewhere to relax and rejuvenate. The narrator makes it clear that a vacation is something that he and his lover have been planning for a long time. And now the chance presents itself where they can disappear and have fun.

“Two Tickets to Paradise” embodies the concept of escape and new beginnings. The “two tickets” symbolize the opportunity for the couple to find their slice of paradise.

16. “Vacation” By G.R.L.

Don’t be fooled by the upbeat sound of “Vacation” by the girl group G.R.L. When you listen closely to the song, you’ll realize it’s about breakup.

In the lyrics, the narrator has just broken up with her lover and deals with emotional turmoil. Thankfully, she’s got friends who know what to say and do to cheer her up.

The song suggests that a vacation can help her cope with the situation, emphasizing the therapeutic potential of taking a break and focusing on self-care. And what better way to do that than with friends who have your welfare at heart.

17. “Kokomo” By The Beach Boys

The American rock band The Beach Boys has the perfect idea for that ideal vacation with a loved one. Want to know what it is? Listen to their 1988 single “Kokomo.”

The title refers to a fictional island off the Florida Keys. For the narrator, it’s where he wants to take his lover for some time away from the hustle and bustle of life. He envisions spending time on the beach with a “tropical drink melting in your hand.”

Aside from the fictional Kokomo, the song references real Caribbean Islands, including Bermuda, Bahamas, Key Largo, and Montego.

18. “Island Song” By Zac Brown Band

Lead vocalist Zac Brown of Zac Brown Band loves the ocean and island life. That is reflected in their single “Island Song,” a celebration of the quintessential island vacation.

The lyrics find the narrator “unwinding down in the islands.” He revels in the company of friends while indulging in drinks, dancing, and music, all against the backdrop of the picturesque islands. This mirrors typical vacation activities. These carefree and fun-filled moments are what make vacations memorable.

And so the narrator urges his listeners to come with him to celebrate and relax. The islands provide a simple life and connection with nature, guaranteed to uplift your spirit.

19. “Miami” By Will Smith

Miami, Florida, is known for its many amazing beaches. It’s no surprise that a song would be written about this popular vacation destination. Will Smith‘s “Miami” captures the lively atmosphere of this city, making it a perfect anthem for a vacation.

The lyrics portray Miami as an exciting and glamorous destination with beautiful beaches, warm weather, and a buzzing nightlife. It’s about the allure of South Beach, a popular vacation spot known for its parties, clubs, and diverse culture.

Here, the narrator finds the perfect place for fun, excitement, and unique experiences. He soaks up the sun, enjoys the vibrant nightlife, and parties all day.

20. “Club Tropicana” By Wham!

A tropical paradise epitomizes the ultimate vacation fantasy. That’s the idea behind the song “Club Tropicana” by Wham!

The title represents the idea of an idyllic getaway. It’s a destination where people can go to escape the worries of life and indulge in pleasure and relaxation. It’s a paradise where one can drink to his heart’s content and party all day and night.

The lyrics further embody the abundant joy and carefree spirit associated with holidays. The only thing missing, according to the song, is the sea. But the overall atmosphere of fun and freedom makes up for it.

21. “Anywhere” By Rita Ora

When you’re in the company of someone you love, it doesn’t matter where you go, just as long as you’re together. This is the idea Rita Ora sings about in “Anywhere.”

In the lyrics, the narrator longs for change or a break from routine – all elements associated with the idea of going on a vacation. The lines “A million miles from L.A., Just anywhere away with you, I know we’ve got to get away” express the desire to be somewhere else, anywhere but the current location. This resonates with the feeling many have when they crave a vacation.

At its core, “Anywhere” reflects the yearning for escape and the allure of vacation with a loved one. It’s about the urge to venture into the unknown to experience freedom and excitement.

22. “Come Fly With Me” By Frank Sinatra

Although “Come Fly with Me” by Frank Sinatra is not a song that mentions “vacation,” it’s an invitation to travel and experience the world. This makes it highly relevant to the theme of vacation.

The song paints a picture of a globe-trotting adventure that takes listeners to various exotic locations. The narrator implores his listener to escape from the ordinary and embark on an exciting trip to Bombay, Peru, and Acapulco Bay.

These destinations imply an exciting exploration of diverse cultures and landscapes. The song celebrates the freedom and excitement that travel brings.

23. “Summer Holiday” By Cliff Richard And The Shadows

Another song that embodies the essence of a vacation is “Summer Holiday” by Cliff Richard and the Shadows. At its core, it’s about the joy of living in the moment and embracing the opportunities that come our way.

The song encourages listeners to take a break from everyday life and seek adventure through a holiday. And so, the narrator and his partner are going on a summer holiday that may last a week or two.

What they have in mind is a place “where the sun shines brightly” and “where the sea is blue.” They look forward to having fun, laughing, and not worrying about anything else.

24. “Those Lazy Hazy Crazy Days Of Summer” By Nat King Cole

We’re almost at the end of our list with “Those Lazy Hazy Crazy Days of Summer” by Nat King Cole. The narrator reminisces about the carefree, idyllic days of summer when life was simple and full of joy.

The song paints a picture of picnics on the beach, drinking, and drive-in movies — typical activities associated with a summer vacation. It invites listeners to escape from the monotony of life and lose themselves in the magic of summer.

The lyrics reflect the laid-back, fun-filled nature of summer days. They suggest the “lazy,” “hazy,” and “crazy” aspects of this season.

25. “Permanent Vacation” By Aerosmith

Our last song on the list reflects what many of us long for a never-ending holiday! Aerosmith knows this all too well in their 1987 single “Permanent Vacation.”

The lyrics describe the narrator receiving a letter from a friend who is in Montego Bay, a popular vacation spot in Jamaica. He acknowledges his need to get away and give himself a “permanent vacation.”

This sparks a desire in him to leave his current life behind and head to the tropical paradise. In essence, the song is about a yearning for an escape from the daily stresses to a place where one can live freely.

Summing Up Our List Of Vacation Songs

Whether it’s a summer holiday or a dream of a permanent vacation, every holiday has its unique charm and significance that adds to the overall richness of life.

Remember to take a vacation every now and then because you deserve it. It’s your chance to rejuvenate, explore new places, and make unforgettable memories.

So that’s it for our topic today. We hope you found new songs to add to your ultimate vacation playlist.

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Dan Farrant, the founder of Hello Music Theory, has been teaching music for over 15 years, helping hundreds of thousands of students unlock the joy of music. He graduated from The Royal Academy of Music in 2012 and then launched Hello Music Theory in 2014. He plays the guitar, piano, bass guitar and double bass and loves teaching music theory.