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10 Best Songs About Vacation

10 Best Songs About Vacation

With summer vacation on the horizon, it’s the perfect time to start getting in the holiday spirit. Vacation can be a time to rest, re-energise and discover new things, so it’s not a surprise that so many artists have found inspiration whilst traveling and created so many best songs about vacation.

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From tropical adventures to poolside lounging, these songs will get you excited no matter what kind of vacation you’re in for. And if you’re dreaming of a staycation and some downtime in your own home, then you can still put in your headphones and enjoy from the safety of your bed. Here are our 10 favorite best songs about vacation and taking some well-deserved time off. 

“Holiday” – Madonna

This classic track from Madonna is brimming over with vacation joy. A refrain of “Holiday! Celebrate!” leaves no room for uncertainty – we are traveling away, and we are thrilled about it. A good vacation is the cure for all the world’s ills according to Madonna. 

“Holiday” was Madonna’s first mainstream hit in several countries including the US and UK, but it was never originally intended to be a single. The song proved an unexpected hit, getting picked up by radio stations thanks to its infectious hook. 


“Shotgun” – George Ezra

Ezra is ready to take off in “Shotgun”, a laidback hit that propelled the singer into a new stage of his career. Ezra dreams of a European road trip down sunny roads and past unfamiliar architecture and stakes his claim on the most popular seat in the car. The song contains all the summer vibes you could wish for, including an obligatory mention of bikini bottoms and a very British shoutout to lager. 

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“Permanent Vacation” – Aerosmith

Aerosmith decide to live everyone’s dream in this energetic ode to warmer places – specifically St Tropez, a place that they “really, really need”. It’s an invigorating getaway track, other than a slight detour in which Steven Tyler starts insulting his sister. 

“Permanent Vacation” was the title track of Aerosmith’s ninth studio album of the same name, which marked their shift into pop-metal. It’s a shift you can hear in this track, with its upbeat chorus and jaunty, Beach Boys-esque melody. 


“Vacation” – The Go-Go’s

Who amongst us doesn’t dream of running away to a tropical island to shake off heartbreak? The Go-Go’s lament a love affair gone sour in this new wave track and resolve that the only cure is a vacation “meant to be spent all alone”. However, they find that they may have underestimated how easy it is to get an ex out of your head, even on holiday. The track was first released on vinyl in 1982 and also had a holiday-inspired B-side – “Beatnik Beach”. 


“Leaving On A Jet Plane” – John Denver

This 60s track has remained the saddest song about flying away on an airplane since it was first written. We don’t know why the couple Denver sings about are separating, and we don’t know how long for, but we do know that neither of them are happy about it. Denver himself has admitted that the track strikes a “lonely and anguished” chord in him. 

A cover version by folk group Peter, Paul and Mary made the song a hit, allowing Denver to reclaim it in later years once he became more successful. Denver never revealed what the motivation behind the track was, but the cover was widely assumed to be referencing the Vietnam War. 


“Vacation” – Dirty Heads

There’s no need to go far from home to get that holiday feeling according to the Dirty Heads. They’re on vacation everyday thanks to a successful music career and the opportunities that come with it. Most of us can only dream of having a career that feels like a holiday, but if you’re one of the lucky few, then congrats! Feel free to happily bop along to this track. 


“Island In The Sun” – Weezer

Weezer are so relaxed on their trip that it’s hard for them to find the words to express it, or even to have a single thought without their minds drifting happily away. They’re truly in a world of their own – an enviable state of bliss. 

“Island In The Sun” is often ranked up with the best Weezer songs due to its cheerful hook and impressively laidback lyrics. Despite this, it was not initially planned to be on Weezer, the band’s 2001 album, but was included at the last minute. 


“Holiday” – Vampire Weekend

This one will be relatable for many – Vampire Weekend are burying down under the covers and waiting it out until the holidays roll around. The song and especially the music video were intended to exemplify the band’s ‘fish out of water’ feelings as they navigated life in Los Angeles and attempted to fit in, wondering if a little time away would fix all of their problems. We’ve all been there. 


“Margaritaville” – Jimmy Buffet

Buffet rattles through all the cliches you can expect to see on holiday in this breezy track about Florida and a particular drink that Buffet discovered there. It became his most recognisable track, and even led to Buffet opening a chain of restaurants under the same name, so that fans could literally escape to Margaritaville. There’s even one in Key West, where the song is set. 


“Kokomo” – The Beach Boys

Written for the film Cocktail, “Kokomo” describes a fictional utopia near Florida Keys where two lovers enjoy an idyllic island vacation on the beach. The song also references plenty of real islands, but none of them seem quite as idyllic as Kokomo. In contrast to the remote, peaceful island described in the song, the video was filmed at Walt Disney World in Florida. 

Final thoughts

No matter where you’re going – or not going – this summer, the right playlist can set the tone for the best vacation of your life. Just get some of these best songs about vacation going, slather on the sun-cream, and turn the music up.