Out Of Office’s Best Holiday Songs

Madonna, Janet, Will Smith, Cliff Richard, Katy Perry, Dizzee Rascal? We've spent far too long debating this, but here's our shortlist. Tell us yours!

It is undoubtedly a contentious issue, what is your favourite holiday or vacation song? In the USA a holiday song means something like Mariah Carey’s All I Want For Christmas Is You. But over here in the UK a holiday song makes us dream of sunshine, lying on a beach and our favourite summer holiday.

Now our boss is a huge Janet Jackson fan so he’s been trying to influence this list into a list of the top Janet Jackson summer songs, but we thought we should at least let some others in on the list so without further ado here is the Out Of Office list of our favourite holiday songs.

Madonna, Holiday

What an absolute classic. I mean the video might be pretty cheap, but Madonna’s Holiday is synonymous with that feel good factor of being away and enjoying the summer.

Dizzee Rascal, Holiday

Dizzee Rascal certainly copied Madonna’s song title but that is probably where the comparison stops. This tune from 2009 commands us to “fly away, drive away and get away,” if we’re doing nothing of course. So any time you find yourself doing nothing, you best follow Dizzee’s orders and run to the airport as fast as you can on jump on the first plane out of the country.

Janet Jackson, Whoops Now

We told you we were forced to do it. Our boss’ love of Janet Jackson borders on obsessive. He has met her (and interviewed her in his old job) several times. The most famous Jackson sibling still alive released Whoops Now in 1993 and the song became renowned for telling all of those people who couldn’t leave work because their job was being too demanding to think again and escape with their friends anyway. Not that we advocate bunking off work, but there’s a certain joy that comes with setting that Out Of Office corespondent isn’t there knowing that you won’t be back at your desk for a few days.

Will Smith, Miami

Put your hands up if you have visited Miami. If your hand isn’t raised right now then stop what you are doing and book one of our Miami holidays. This absolute tune from the Fresh Prince instructs you to party all night on the beach until the break of dawn. Who are we to argue? Yes, Big Willy.

Cliff Richard, Summer Holiday

No matter whether you love or hate him you cannot deny that Sir Cliff Richard recorded a corker with Summer Holiday. The 1963 song and movie still takes us back to our childhood (no matter what age you are!) and those guitar riffs are the stuff of legend.


John Travolta and Olivia Newton-John, Summer Nights

It turned colder, that’s where it ends. Or so they say. This song screams campness, colour and vivacity and will go down as one of our favourite summer tunes of all time. Oh how we wish John Travolta and Olivia Newton-John had lived happily ever after in real life.

Katy Perry, California Gurls

Candyfloss, a world that is like a modern day Wonkaland and the beautifully gorgeous Katy Perry make for this bubblegum pop song that drives us to a more exciting place than the desk that we presently write this from. Oh to dream. Take us on holiday RIGHT NOW!

What next?

To get going, please submit an enquiry below and one of our expert team will get back to you within the next 24 hours to discuss your requirements. All the prices on our website do not include flights, but we can, of course, arrange them for you and include them in your quote.

Remember, there is no booking fee for using our expert team to plan and book your trip.

Make an Enquiry

Call the team now for a chat on +44 (0)20 7157 1570.
Tap to Call