Like the idea of a workcation? This travel company is giving away $10,000 so you can take a trip anywhere in the world

Do you like the idea of being able to work from anywhere? Online travel agency Kayak is wanting to show you that this dream can be a reality. Whether you’re relaxing in the Maldives, skiing in the Rocky Mountains or sunning yourself in Spain – and juggling work at the same time – they want to show how many companies are changing their remote work policies, and how you can combine the luxury of life and travel at the same time. And what’s more, they are giving one lucky person $10,000 to prove it. With Kayak’s new Roam Remotely sweepstakes, the grand prize winner will receive an expenses-paid trip worth up to $10,000 so that they can work from anywhere they want. The prize comes in the form of four Amex gift cards valued at $2,500 each for a $10,000 total. There is no purchase necessary, but you do have to be US resident from one of the 50 states or District of Columbia. All you need to do to enter is head to Kayak’s Roam Remotely sweepstakes page and complete this short form. The closing date for entries is 3rd February 2022, midday Eastern Time. All entrants should check and consult with their respective employer(s) regarding any immigration, tax, and other legal considerations when considering whether to work remotely from another destination outside of their respective state. Please see the website for full terms and conditions. Good luck! If you’d like to be notified of other competitions like this one in the future, be sure to subscribe to our mailing list.

Paul Johnson

Paul Johnson is Editor of A Luxury Travel Blog and has worked in the travel industry for more than 30 years. He is Winner of the Innovations in Travel ‘Best Travel Influencer’ Award from WIRED magazine. In addition to other awards, the blog has also been voted “one of the world’s best travel blogs” and “best for luxury” by The Daily Telegraph.

Did you enjoy this article?

Receive similar content direct to your inbox.


  1. On paper, working remotely from anywhere in the world, looks attractive. As employees can base themselves where they are getting a lot of enjoyment from their hobbies (biking, hiking, surfing etc) that satisfaction may well spill over to their jobs too. It ought to help employee retention. I’ve got a feeling that the small print might stop some employees from living the dream.

    1. Yes, in theory, I think it’s great to be able to have a lifestyle like this, potentially for both employer and employee. However, I think there are plenty of potential pitfalls and it therefore won’t work for everyone… and indeed it’ll just be impossible to implement for some, depending on their line of work.

  2. My take on the situation is that in future where you work is going to be big in deciding on jobs and careers. Employees used to take a job because it had potential for travel for work. Now they’re going to want to take care of the travel for themselves. Interviews will be about seeing if you can get a green light to work wherever you like.

    1. This is why I chose to run my own business. I immediately have that freedom without being answerable to anyone. Of course, it can have its downsides, but for me the positives easily outweigh any negatives.

Leave a Reply

Your email address will not be published. Required fields are marked *