20 Songs About Vacations And Holidays

Vacations and holidays hold a special place in my heart, serving as cherished moments that allow us to escape the routine of everyday life. Whether it’s lounging on a sun-soaked beach, exploring vibrant cities, or enjoying a cozy cabin in the mountains, these experiences create lasting memories that we carry with us long after the trip ends. Music has a unique way of capturing the essence of these adventures, evoking feelings of joy, nostalgia, and wanderlust. 

In this playlist, I’m excited to share 20 songs that perfectly encapsulate the spirit of vacations and holidays. Each track tells a story, transporting us to different destinations and reminding us of the bliss that comes with a well-deserved break. 

1. “Holiday” by Madonna

Madonna’s “Holiday” is a classic pop anthem from her debut self-titled album, released in 1983. The song was written by Curtis Hudson and Lisa Stevens and became Madonna’s first hit single, reaching No. 16 on the Billboard Hot 100 and No. 6 in the UK. “Holiday” is celebrated for its upbeat and carefree vibe, encouraging listeners to take a break from their everyday lives and enjoy a moment of relaxation and joy. The track’s success marked a turning point in Madonna’s career, establishing her as a pop icon. Despite its age, “Holiday” remains a timeless track often associated with the spirit of taking a break and enjoying life.

2. “Miami” by Will Smith

“Miami” is a vibrant tribute to the city of Miami by Will Smith, featured on his debut solo album Big Willie Style (1997). Released as a single in 1998, the song peaked at number 17 on the Billboard Hot 100. It samples The Whispers’ 1979 hit “And the Beat Goes On,” adding a disco-infused backdrop that complements the song’s festive and lively portrayal of Miami’s heat, style, and nightlife. The accompanying music video, which won an MTV VMA for Best Male Video, showcases Will Smith and his band escaping the cold of Philadelphia for the sunny beaches of Miami, capturing the essence of a fun and carefree holiday.

3. “Vacation” by G.R.L.

“Vacation” by G.R.L. is the debut single from the American-British-Canadian girl group, released in 2013. The song, written by Bonnie McKee, Dr. Luke, Max Martin, and Cirkut, is an upbeat breakup anthem that emphasizes empowerment and moving on. It was initially released as a B-side to Britney Spears’ “Ooh La La” for The Smurfs 2 soundtrack. The lyrics convey a sense of freedom and fun, as the protagonist decides to take a vacation from a past relationship and enjoy life with friends. The song’s catchy and bubbly nature makes it a fitting addition to any holiday playlist.

4. “Vacation” by Dirty Heads

Dirty Heads’ “Vacation” is an uplifting reggae-rock anthem that celebrates the joy of loving one’s work. Featured on their sixth studio album, the song’s catchy chorus, “I’m on vacation every single day ’cause I love my occupation,” highlights the idea that when you love what you do, every day feels like a holiday. The song encourages listeners to pursue a life where work is a source of happiness and fulfillment, promoting a positive and proactive approach to life. Its motivational message and upbeat rhythm make it a perfect song for those looking to embrace a carefree and joyous lifestyle.

5. “Island In The Sun” by Weezer

“Island in the Sun” by Weezer, released in 2001 as the second single from their self-titled album (also known as the Green Album), is a quintessential song about escapism and the desire for a carefree existence. Written by Rivers Cuomo, the song invites listeners to imagine an idyllic getaway where the worries of the world melt away. The lyrics, “On an island in the sun / We’ll be playin’ and havin’ fun,” evoke a sense of liberation and joy, while the repetitive “Hip, hip” chant adds to the carefree vibe of the song. The island serves as a metaphor for a mental or emotional place of peace and happiness, making it a perfect anthem for those seeking a mental escape from their daily grind.

6. “Toes” by Zac Brown Band

“Toes” by Zac Brown Band is a staple summer song that vividly describes a beach vacation. Released in 2009 as a single from their album The Foundation, the song was inspired by Wyatt Durrette’s vacation in Key West, Florida. The lyrics, “I’ve got my toes in the water, ass in the sand, not a worry in the world, a cold beer in my hand,” encapsulate the essence of relaxation and enjoyment that comes with a beach holiday. The song contrasts the bustling routines of city life with the laid-back pace of a beach town, emphasizing the stress-relieving power of a beach getaway. “Toes” became a significant hit, reaching the top of the country charts and resonating with listeners as an anthem of escapism and leisure.

7. “Island Song” by Zac Brown Band

“Island Song” by Zac Brown Band, featured on their 2012 album Uncaged, brings a fun reggae vibe while maintaining the band’s signature sound. The song is about escaping to an island paradise, enjoying the simple pleasures of life, and having a good time. The lyrics describe a beautiful woman who goes to the islands in search of an island lover, capturing the carefree and romantic essence of a tropical holiday. The upbeat rhythm and catchy chorus make it a lively and enjoyable track that encourages listeners to unwind and enjoy the moment, making it a perfect addition to any vacation-themed playlist.

8. “Summertime, Summertime” by The Jamies

“Summertime, Summertime” by The Jamies is a classic rock and roll song from 1958 that celebrates the end of the academic year and the beginning of summer fun. Written by Tom Jameson, the song became a nationwide hit and is known for its fugal introduction and catchy melody. The lyrics, “It’s Summertime, Summertime, Sum, Sum, Summertime,” invite listeners to join in the summertime activities, including swimming, dancing, and romancing. The song’s upbeat and joyful nature makes it a timeless anthem for the summer season, capturing the excitement and freedom associated with school holidays and warm weather.

9. “Come Fly With Me” by Frank Sinatra

“Come Fly with Me” is a classic song by Frank Sinatra, released in 1958 as the title track of his album Come Fly with Me. Composed by Jimmy Van Heusen with lyrics by Sammy Cahn, the song invites listeners on a glamorous journey to exotic destinations like Bombay, Peru, and Acapulco Bay. The lyrics paint a vivid picture of adventure and leisure, evoking the spirit of the Jet Age when air travel was becoming more accessible to the public. Sinatra’s smooth vocals and the song’s romantic undertones make it an anthem of escapism and possibility, encouraging listeners to break free from their everyday lives and explore new horizons.

10. “Anywhere” by Rita Ora

“Anywhere” by Rita Ora is a dance-pop and electropop song from her second studio album, Phoenix (2018). Released as a single in October 2017, the song was written by Ora, Ali Tamposi, Brian Lee, Nick Gale, and its producers Alesso, Watt, and Sir Nolan. “Anywhere” is about escapism and the desire to leave behind the mundane for an adventurous journey with a loved one. The lyrics, “Take me anywhere, anywhere away from here,” capture the longing for freedom and exploration. The song received positive reviews and became a commercial success, reaching the top 10 in multiple countries. Its accompanying music video, set in various locations around New York City, further emphasizes the theme of adventure and escape.

11. “Pontoon” by Little Big Town

“Pontoon” by Little Big Town is a country song released in April 2012 as the lead single from their fifth studio album, Tornado. Written by Natalie Hemby, Luke Laird, and Barry Dean, the song celebrates the simple pleasures of a leisurely day on a pontoon boat. The lyrics describe a carefree scene of partying on the water, with lines like “Makin’ waves and catchin’ rays up on the roof.” The song’s laid-back vibe and playful lyrics make it a perfect summer anthem. “Pontoon” became Little Big Town’s first No. 1 single on the Billboard Hot Country Songs chart and won the 2013 Grammy Award for Best Country Duo/Group Performance.

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

“Hot Fun in the Summertime” is a 1969 hit by Sly and the Family Stone, released just before their iconic performance at Woodstock. Written and produced by Sly Stone, the song celebrates the joys of summer with its upbeat and nostalgic lyrics. The song reached No. 2 on the Billboard Hot 100 and No. 3 on the Billboard soul singles chart. It is considered one of the greatest summer anthems, with its cheerful melody and references to summer fun and games. The song’s use of strings, a rarity for the band, adds a unique touch to its sound. “Hot Fun in the Summertime” has been covered by various artists and remains a timeless classic that encapsulates the essence of summer.

13. “Vacation” by Thomas Rhett

“Vacation” by Thomas Rhett is a country pop song released on June 13, 2016, as the fourth single from his second studio album, Tangled Up. The song, co-written by Rhett and several others, features an interpolation of War’s “Low Rider” and is characterized by its upbeat and fun lyrics that celebrate the carefree spirit of a vacation. The music video, directed by TK McKamy, showcases Rhett enjoying various activities in Hawaii with his family and friends, emphasizing the song’s theme of relaxation and fun. Despite its lively nature, “Vacation” was Rhett’s first single to miss the top 20 on the charts, peaking at No. 30 on the Country Airplay chart.

14. “Margaritaville” by Jimmy Buffett

“Margaritaville” is a 1977 song by Jimmy Buffett from his album Changes in Latitudes, Changes in Attitudes. This iconic track, which reached No. 8 on the Billboard Hot 100, epitomizes the laid-back, carefree lifestyle associated with tropical vacations. The lyrics describe a leisurely day spent in a tropical paradise, complete with margaritas and minimal worries. The song’s enduring popularity has made it synonymous with Buffett’s brand, leading to a franchise of restaurants, resorts, and merchandise under the Margaritaville name. “Margaritaville” has been inducted into the Grammy Hall of Fame and selected for preservation in the United States National Recording Registry for its cultural significance.

15. “I’m On Vacation” by Rhett and Link

“I’m On Vacation” by Rhett and Link is a comedic song that humorously chronicles the escapades of two friends on a wild vacation. Known for their YouTube channel and comedic music, Rhett and Link bring their signature humor to this track, which details various exaggerated and outlandish vacation activities. The song’s playful lyrics and upbeat tempo make it a fun addition to any vacation-themed playlist, capturing the joy and absurdity that often accompany a much-needed break from work.

16. “Vacation” by The Go-Go’s

“Vacation” by The Go-Go’s is a 1982 single from their album of the same name. The song reached No. 8 on the Billboard Hot 100 and is celebrated for its catchy melody and upbeat tempo. Written by Go-Go’s bassist Kathy Valentine, the song reflects the bittersweet emotions of leaving behind a special place or person after a vacation. The music video, which features the band in various vacation scenarios, including a memorable water-skiing sequence, adds to the song’s fun and nostalgic feel. “Vacation” remains one of the Go-Go’s most beloved tracks and a quintessential summer anthem.

17. “Some Beach” by Blake Shelton

“Some Beach” is a country song by Blake Shelton, released in July 2004 as the second single from his album Blake Shelton’s Barn & Grill. Written by Rory Feek and Paul Overstreet, the song humorously details the frustrations of everyday life, such as dealing with road rage and long waits at the dentist, while the narrator wistfully imagines escaping to a serene beach. The title plays on a Southern dialectal form of the epithet “son of a bitch,” adding a clever twist to the song’s theme of escapism. The song became Shelton’s third number one hit on the Billboard Hot Country Songs chart and spent four weeks at that position, resonating with listeners who dream of a peaceful getaway amidst life’s annoyances.

18. “Summer Holiday” by Cliff Richard and The Shadows

“Summer Holiday” is a classic pop song recorded by Cliff Richard and The Shadows, released in February 1963. Written by Bruce Welch and Brian Bennett, the song is the title track from the film Summer Holiday. It captures the carefree spirit of a summer vacation with lyrics that celebrate taking a break from work and enjoying fun and laughter. The song was a major hit, reaching number one on the UK Singles Chart and becoming one of Richard’s best-known titles. Its cheerful melody and optimistic lyrics make it a timeless anthem for summer holidays.

19. “Permanent Vacation” by Aerosmith

“Permanent Vacation” is a song by Aerosmith from their 1987 album of the same name. The album marked a significant comeback for the band, featuring a more polished, commercial sound that appealed to a broader audience. The song itself embodies the idea of a perpetual holiday, with its upbeat tempo and catchy chorus. The album Permanent Vacation is often credited with revitalizing Aerosmith’s career, blending their hard rock roots with pop sensibilities. The title track, with its island-vibe outro and Stephen Tyler’s harmonica, captures the essence of a never-ending party and carefree lifestyle.

20. “Two Tickets to Paradise” by Eddie Money

“Two Tickets to Paradise” is a 1978 rock song by Eddie Money from his debut self-titled album. Written by Money himself, the song tells the story of a man promising his lover an escape to a paradise where they can leave their troubles behind. The lyrics, “I’ve got two tickets to paradise / Won’t you pack your bags, we’ll leave tonight,” evoke a sense of spontaneous adventure and romantic escapism. The song became a staple on classic rock radio and remains one of Eddie Money’s most enduring hits, symbolizing the dream of a perfect getaway.

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Serena Whitfield

Serena Whitfield is the founder of PlaylistCurator.org. She’s a musician who writes songs for bands. She studied music at the University of Oxford and graduated with distinction. With her expertise, she knows how to review songs and understand what makes good and bad music. Every playlist on our platform is approved by her before publishing to maintain top-notch quality. If you want her to check out your song and maybe get featured on our playlist, submit your song for Serena to evaluate.