Vacations can be a time to rest, re-energize and discover new things, so it’s not a surprise that so many artists have found inspiration whilst traveling and have created many songs about vacationing.
From bucket list adventures to poolside lounging, these songs have certainly made me crave a little R and R away from home.
If you’re dreaming of a staycation and some downtime at home, then you can still don your headphones and fantasize about your next trip away.
Here are the best songs about vacations and taking some well-deserved time off.
Top Songs About Vacation
“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.
“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.
“Holiday” – Little Mix
Little Mix feel like they’re on holiday all year long when they’re in love. Describing a warm new love, they explain how their new lover makes them feel like they’re on vacation whenever they touch. He practically puts the sun in their sky and they’re looking forward to some long, hot nights.
This easy dance track was just as much fun to write as it is to listen to. Whilst penning the summer anthem, the group revealed that they were drinking champagne in the studio. Wanting to write something that would match their happy, carefree vibes, they came up with ‘Holiday’.
“On The Beach” – Chris Rea
The beach is a romantic place, as Chris Rea sets out in ‘On The Beach’. Whilst the lyrics of the song aren’t that specific, Rea makes it very clear that the beach in his memory was the setting of a vacation romance that he looks back on fondly.
This beach isn’t just romantic, but mystical. “The secrets of the summer I will keep,” sings Rea. “The sands of time will blow a mystery.” This summer romance may be staying largely under wraps, but it’s no secret how much Rea obviously enjoyed his vacation.
“Come Fly With Me” – Frank Sinatra
Sinatra’s winning vocals seduce the listener into holiday mode as he invites them on an international flight somewhere exotic. Bombay, Peru, it doesn’t matter – Sinatra just wants to go somewhere. He’s convinced that a vacation is the key to a perfect romance and he can’t wait to get started. The weather is apparently perfect for “a flying honeymoon” and he’s keen to take full advantage.
Sinatra already had a bit of a reputation as a jet-setting romancer, so ‘Come Fly With Me’ fit perfectly with his image. It became one of his most popular tracks and was often sung at concerts.
“Wake Up” – Hilary Duff
Duff is tired of the media speculation – she needs a vacation pronto. This won’t be the kind of trip where she spends her days relaxing by the beach, though. Instead, Duff is looking to dance her worries away in any city around the world that she can get to. “Could be New York, maybe Hollywood and Vine,” she sings, “London, Paris, maybe Tokyo…” There’s something happening wherever Duff is, so any destination could be her perfect party vacation.
“Anywhere” – Rita Ora
Rita Ora is itching for a vacation in this wistful dance track. She doesn’t mind where it is, as long as her lover is there too. Keen to go somewhere where no one knows her name, her perfect vacation will involve no involvement from the media, but just a few days of peace with the person she loves.
Ora wrote ‘Anywhere’ after growing sick of her routine in LA. She was dreaming about getting away from the city and channelled her wanderlust into her studio session. The video, shot on the streets of New York, involved her kissing random passers-by.
“The Sea” – Morcheeba
Have you ever felt like you’ve left part of your heart behind on holiday? So have Morcheeba. The band describe a trip to the seaside that they can’t stop dreaming about. The scavenging seagulls and crashing waves have a hold on them, and now they’re finding themselves intensely missing their vacation. After living free by the sea, they’re finding it hard to adjust back to everyday life.
“Summer Nights” – John Travolta, Olivia Newton-John
This classic musical theatre song from Grease depicts a teenage summer romance. Whilst on vacation with their respective families, Sandy and Danny embark on a fling that ends when the weather grows colder. Still, they’re left with plenty of memories from their vacation, which they eagerly relate to their friends. Teenage cliches like walking along the beach, holding hands and staying out a little later than they’d usually be allowed all feature.
“Summer Holiday” – Cliff Richard & The Shadows
“We’re all going on a summer holiday,” sings Cliff Richard cheerfully. “No more working for a week or two.” This gentle ditty is the ultimate feel-good, relaxed celebration of that holiday feeling. With its happy riff and optimistic lyrics, ‘Summer Holiday’ captures how we all feel heading off on vacation.
‘Summer Holiday’ was written for the movie of the same name starring Cliff Richard. Despite being released in the winter, the song topped the UK charts for 14 weeks.
“Holiday” – Dizzee Rascal
Dizzee Rascal is convinced that the listener needs a vacation. He’s even written their packing list for them – their passport, a bikini, and… that’s it. Whether it’s a rave or a relaxing beach trip, he’ll do whatever they want, as long as they’re ready to jet off with him. His only stipulation is that they don’t look at his ugly passport photo and that they let him buy them as much food as they can eat. Sounds like a good deal.
“Summer Nights” – Rascal Flatts
Rascal Flatts couldn’t be more ready for a vacation. It’s time to wind the car roof down, get their flipflops off and head to the beach. They’re not looking to relax in the sun though – they’re eagerly awaiting the sunset so that their holiday can really begin. The most exciting part of their summer vacation happens when it’s getting dark and everyone’s a few drinks in. They’ve got plenty of instructions for the guys, but the ladies? “Y’all keep doing y’all’s thing.”
“Run Away With Me” – Carly Rae Jepsen
Carly Rae Jepsen wants to get to know her new lover on some distant shores, and she wants to leave now. She tells him to pack a bag so that they can leave while everyone’s still sleeping and run away on vacation together. There’s no specific destination in mind – “Baby, take me to the feeling,” she tells him instead. Any vacation spot is perfect as long as it’s just the two of them flying to it in the clouds over the city.
Final Thoughts
No matter where you’re going – or not going, the right playlist can set the tone for the best trip of your life. Just get this vacay playlist organized, slather on the sun-cream, and turn the music up.
Caitlin Devlin is a music, entertainment and lifestyle writer based in London. When she’s not creating playlists for Repeat Replay, she’s reviewing gigs and interviewing artists for Ticketmaster UK and thinking about what her Spotify Wrapped will look like this year.