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How to Win Travel Competitions & Get a Free Holiday!

If you know what to look for to win a free trip, and which ones to enter, you stand a much better chance of winning the thing. 

There are certain rules to winning holiday competitions, which I’ll go through below. There’s a knack. 

I want to tell you how to win a travel competition, or at least, how I did. Five times.

When I first started travel blogging, back in 2011, I’d do anything to travel more. I was earning £19k a year, living in London and going out every weekend. I didn’t have the money to spend on all the trips I wanted to go on, and I needed new material to write about.

– [Updated April 2019] –

Winning travel competitions

How to win free trips

I decided to start entering free holiday competitions. Part of my job at the travel company I worked at was coming up with ideas for competitions to win holidays, and making them stand out so people wanted to enter them.

This meant that researching what other travel companies were doing for holiday comps was all in a day’s work. I needed to look at their methods of entry, what kind of holiday giveaways they were doing and who won them.

Every week I spent more time than I probably should of some time attempting to win the travel competitions I found. Well, seeing as I was already on the page I might as well. 

And then I started winning holidays.

Trigger warning: might make you jealous so just scroll down to the ‘how to win holiday competitions’ bit. 

Travel competitions I’ve won

Logo for VickyFlipFlop

1. G Adventures trip from Zanzibar to Nairobi

Travel competitions

It was some sort of anniversary for the Queen at the time, back in 2012, so the travel company G Adventures asked their Facebook audience to dress up as a King or Queen, send in a pic, and the winner would win the trip.

I dressed up as Martin Luther King, in a suit and ‘tasche, and only went on to win the blummin thing. Shame I can’t find the photo now, probably for the best.

I can vividly remember running on the treadmill at the gym at Swiss Cottage, thinking about how much I wanted the G Adventures trip. I remember saying to myself that if I won, I was really going to make a go of this travel blogging malarkey. And I did. So here I am, four years later and loving the travel blogger life.

And that trip was awesome.

Pin me for laterhow to win travel competition

Winning travel competitions

That trip was the first of a glorious winning streak for me. Over the next two years I went on to win:

2. – Trip for two to Sharm el Sheikh

3. – Two flights to Amsterdam

4. – Trip for two to Cuba

5. – £300 to spend on a trip to Rhodes

6. – A GoPro HERO4

Holiday competitions on my blog

How to Win Travel Competitions

I make it a point to show off competitions for travel on my blog. Why? Because it’s where I began.

There’s no way I would’ve been able to afford those holidays back in the day.

If I hadn’t have entered that first holiday competition to win the trip from Zanzibar to Nairobi, I wouldn’t have had the confidence in myself that I’d done something cool. Something cool enough to write about and to kick start my travel blog into action.

Follow me on Instagram Stories for the latest travel adventures!


How to win travel competitions

1. The more obscure the entry method to the travel competition, the more chance you have to win.

If you need to make a video, a poem or send some sort of photo to enter the competition then less people will be bothered to enter, and the more reason for you to do so.

The harder is, the less people will enter and the more chance you have. You’re looking for low entry competitions, ok? 

Here are the methods of entry for the travel comps I won…

– Trip for two to Sharm el Sheikh – my business card was pulled out the jar at a blogger meet up.

– Two flights to Amsterdam – I entered by Retweeting on Twitter.

– Trip for two to Cuba – I just signed up to a newsletter with my email address, not my one, my personal one (just in case you wondered). 

– £300 to spend on a trip to Rhodes – another email sign up. 

– A GoPro HERO4 – this was actually a second prize, I had to say why I’d be a good person to win a trip to Papua New Guinea. 

Amazingly, you can see that they were actually all pretty simple methods. Although, I’m sure having a travel blog helped me to win some of them, so really, they were quite difficult as I’d spent so long working on this to make me a worthy winner.

But when I say enter the more difficult ones, with higher barriers to entry, it’s that safari trip I’m thinking of. And that’s an awesome prize to win. You just need to go the extra mile – it’s less crowded there! 

win a free trip

2. Free competitions to win holidays

You should always enter the free travel competitions you see, you never know what might happen. I know for a fact and from experience that many of the ones put on by travel companies have a lot less entries than you might think. You do have a chance.

This one time, I told Kara from about all the travel competitions I enter, and that she should too, and a few weeks later she went on to win a trip to Bali for two.


When I worked at, we had a travel competition to win a trip for two to the Cook Islands. Seriously, we had about ten entries because the method of entry was a video. And people can’t be bothered to make videos. 

The harder the travel comp is, the less people enter, the more chance you have. 

How to win free trips

VickyFlipFlop Story

1. Do you know about Tweetdeck? Well basically it’s a tool that makes Twitter easier to use and follow, and you can set up feeds to follow certain hashtags. At one time I had it set up to follow hashtags like #competition and #win. That way I was seeing every competition that came through.

You can also just log on to Twitter and do this too.

2. Keep your online eyes peeled for holiday competitions that don’t seem to be very well advertised. One of the best ways of doing this is following your favourite companies on Facebook. Always think of creative answers for competitions to be in with the best chance. There’s genuinely no point in entering if you don’t at least try a little bit. 

3. Look at the ending date, if it’s in anything more than a month the competition you’re looking at is probably a scam to just collect email addresses with no intention of ever having any winners.

4. Is it relatively difficult to enter? Then do it now. The more barriers to entry there are, the less entrants there’ll be, and the more chance you have. As I’ve said before. 

5. Does the competition owner do competitions all the time? If so then it’s less likely you’ll win. You’ll have seen magazines that do competitions every week, and will have a few hundred or thousand comp queens who enter every time. That’s not the kind of competition you’re looking for.

For example, I’d rather enter this competition with Rickshaw Travel,
rather than this one with escapism Magazine.

Holiday competitions to enter 

Winning travel competitions

Kinda, but it’s not just luck. You got be in it, to win it.

You could try out comping sites, to find the best travel competitions. Ones like Loquax, Money Saving Expert, Wanderlust and Travel Scoop all feature the latest and greatest holiday comps out there. Spend a rainy Sunday going through and entering them all, you never know. 

Check out Taylor Hearts Travel’s weekly competition round up to win a trip (hopefully). I’m pretty sure that’s where I found the Cuba competition!

Or Rosemary and Pork Belly also do a holiday competition round up, that could be totally worth a look. 

And I’ve actually just gone through and entered loads of competitions on there, so wish me luck. Maybe?

And just one final tip for entering travel competitions: if you’re worried about the inevitable spam, set up a different email address. But, don’t forget to check it! 

Win a free trip

Friends who’ve won a holiday competition

Steve won a flight to Sweden and accommodation for TWENTY people. He was the most popular guy ever when he had a whole section of the plane to himself and his friends. When the airline phoned him to tell him he’d won he totally didn’t believe them and put the phone down on them. This was just a email address to enter competition. 

Steve’s a right jammy one and also won a trip to Peru, to climb Machu Piccu. I know!

*But, we call him jammy but then he does enter every competition he sees! 

Macca won a £250 holiday voucher of his choice, for uploading a Tweet about an event he was at. That was it! 

Jai won a luxury cruise for two by putting her business card in a bowl. She’s also won an amazing holiday to Egypt doing exactly the same thing! 

See, just enter and you don’t know where it might lead!

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