How to win holiday competitions

Blue Waters Resort, Antigua ©
Blue Waters Resort, Antigua

It can be done.
We’re living proof, having had two big holiday wins.

And the feeling you get when you receive that winners email or message is amazing.

Of course you need a lot of luck.

But there are things you can do to increase your chances. So here’s our guide to entering – and winning – holiday competitions.

Blues Brothers Universal Studios Orlando ©rosemaryandporkbelly
Blue Brothers at Universal Studios, Florida

How to find the best holiday competitions

The easiest thing to do is bookmark our holiday and travel competitions page and come back daily or weekly.

Pork Belly curates this list to present genuine competitions, with proper terms and conditions. This diligence helps weed out any of the phoney ones. He highlights particular entry requirements or restrictions to save you time.

You can also subscribe to our newsletter – we send out one a fortnight, featuring six of the best holiday competitions on The Pork Belly List.

But there are hundreds of holiday competitions so here are a few other websites and forums we trust:

SuperLucky Di – packed with news of the latest comps and hints and tips on the best way to increase your chances. Di is a BIG winner herself and her advice is worth heeding.

The Prizefinder, Loquax and Moneysaving Expert – these are user-generated forums which we’ve found to be reliable and useful in sourcing good competitions. Create a profile and you can use the power of algorithms (or gorilla-rithms as Pork Belly calls ’em) to serve up competitions that match what you’re looking for. Also very good for finding ‘closing soon’ comps you may have missed.

Padstow Christmas Festival chefs ©
Meeting the chefs at Padstow Christmas Festival

How to enter holiday competitions

First of all only go in for competitions you really want to win!

Many comps say the prize is non-transferable so please, please, please don’t enter if you can’t go on the set dates or don’t actually want that hotel, destination or experience.

It’s why we never enter cruise competitions – I have no sea-legs at all.
(True – I get seasick while the ship’s still in harbour!)

Plus entering for something you don’t want takes the chance away fom others who do. We don’t enter if the prize is specifically for families with young children, dog-owners or people with accessibility needs.

It’s just not fair.

Islands of Adventure Orlando Florida ©rosemaryandporkbelly
Islands of Adventure, Florida

Second and most important rule is Read The Terms And Conditions

Pork Belly does a scoot through to find if there are any particular issues but always check for yourself that you meet the requirements.

And some comps have rules about what they expect in return – your photos, stories etc which they want to use in future advertising. If you’re not comfortable with this, then don’t enter.

There are hundreds of other comps out there without any such restrictions.

Thirdly look for the unusual.

If all that’s required to enter is to like a Facebook post or provide an email address then you will be one of thousands, perhaps millions of entries.

But if it needs a little effort – a quiz, a few words about why you want to win, a photo, a video – then fewer people will bother and your chances of winning shoot up.

In the days before the internet, when slogans were the popular way to enter a comp, we won four bikes because we took the time to work up a little poem. Mind you we once slaved over a perfect little slogan and won … an oven glove!

Is it safe to enter holiday competitions online?

The answer is yes – but you need to be careful.

Only enter on a device that has a strong virus protection package installed. If you get any sort of alert, don’t go any further. It may be very sensitive and giving a false positive warning but you don’t want to run the risk of being infected with malware, so back away immediately!

There are plenty of comps on trusted sites, it’s just not worth the risk.

If Pork Belly finds something a bit hinky he won’t put it on his list but instead contacts the site owner. Sometimes it’s something they can easily fix and the comp goes up later.

Universal Studios Theme Park Florida ©rosemaryandporkbelly
Universal Studios, Florida

How not to get scammed or spammed when entering holiday competitions

Sites that host competitions may well be safe, but isn’t there a risk you’ll be spammed for ever afterwards?

Well no, not if they’re a legitimate company abiding by the data protection laws that apply in their base country.

But there are steps you can take as well:

  1. Set up a dedicated email account for entering comps. That keeps your personal inbox free of clutter.
  2. Only sign up to newsletters if it is a condition of entry. Most promoters want your email details and will ask you to go on their list, but it won’t affect your chances of winning if you don’t. Be selective.
  3. That said, we often sign up just to see what other offers the company has – it’s easy to unsubscribe if you’re getting too much or it’s not relevant. Legitimate companies won’t hassle you and will appreciate you dropping off the list if you’re no longer interested.
  4. Be selective with comps run on social media platforms. There are some great ones with excellent prizes, but it’s all too easy for less-than-scrupuluous firms to take advantage of a simple ‘like and share’ option. Plus when entry is just the click of a button you will be one among hundreds of thousands. It’s a personal thing but we rarely enter social media based comps at all, and The Pork Belly List only features ones that don’t require a social media account to enter.
Hard Rock Hotel Orlando Florida ©rosemaryandporkbelly
Hard Rock Hotel, Orlando – our family home for 7 days!

Should I pay to enter competitions?

Hmmm .. we never do.

In the UK lotteries are strictly regulated under The Gambling Act and promoters have to be licensed.

But if there is an element of skill involved, however small, then it’s no longer a lottery but a competition and doesn’t come under the Act.

If more than one person gets the right answer, completes the puzzle or whatever the entry requires, then a winner will be drawn at random from all the correct answers.

This can be an email entry or by post. Under the rules, a free entry has to be treated in exactly the same way as a pay-to-enter one, so with a little effort and/or the cost of a stamp you stand just as good a chance of winning.

Other comps have one free entry then you can pay to boost your chances further.

You may also decide you want to pay if you know by doing so you’re supporting a good cause. Some companies run contests where they give a sizeable chunk of what they make to a charity or non-profit organisation.

It’s up to you

As for us? We’ll buy a raffle ticket at a village fete, but that’s as far as it goes.

And finally ….

What’s it like to win a holiday competition?


The feeling when you get that ‘you’ve won’ email or phone call is indescribable.

Your first reaction will be, ‘I don’t believe it!’

And that’s exactly the right way to respond.

Before you reply, check back.
• Did you actually enter that competition?
• Is this the company that’s running it?
• Are the details they’ve given the right ones – can I call a different number and get through to the same person?

Never click on any link in any email until you’re sure it’s legitimate.

If the terms and conditions of the comp are no longer on their website, ask them for a copy so you can refresh your memory of what they’re offering.

Then you can relax and enjoy your win!

The Snow Queen and Jack Frost, Padstow ©
Padstow Christmas Festival

What have Rosemary and Pork Belly won?

We’ve been entering travel competitions on and off for many years and have had two spectacular, amazing and glorious holiday wins.

One was a family holiday at Universal in Orlando, Florida – Hard Rock Hotel, theme park tickets and fast passes.

And here’s a cautionary tale – we nearly didn’t enter!

I’d seen the leaflet and thought, ‘Nah, not a chance’ and popped it in the recycling. Pork Belly salvaged it, smoothed out the crumples, and went ahead and entered.

So never say never – one entry is better than no entry.

Men in Black ride Universal Studios ©rosemaryandporkbelly
MIB at Universal Studios, Florida

The other was our trip to Antigua, staying at Blue Waters Resort.

We’ve also had a few smaller UK travel wins the best one a trip to Padstow for their Christmas Festival – 3 days of eating, drinking and demonstrations.

And next?
Well, we’re still entering, still dreaming.

How about you?
Have you ever won a holiday?
What are your top tips for entering holiday competitions?

All photographs taken while enjoying a competition win copyright ©rosemaryandporkbelly

Where to next?
Holiday and Travel Competitions
Dog-friendly holiday cottages UK
A guide to the Prosecco Road

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