Yes, we do mean when, not if! Keep on checking our holiday competitions page and follow our top tips, and we’re sure you’ll be lucky … eventually.
So let’s fast-forward to that moment when you get the email, message or letter, saying you’ve won a trip of a lifetime.
Here’s where you need this, your ultimate guide to seizing the prize, navigating passport, health, insurance, and visa essentials, after winning that dream holiday.
And if it’s a trip abroad, your first thought will be, ‘Where the heck did I put my passport?’
As it sinks in, you’ll let out a whoop of excitement and rush to tell everyone.
Then you come back down with a bump and go, ‘Now what?’
Don’t worry, we’ve been there. So we’ve made a jet-setter’s checklist, unveiling the essential steps to turn your prize into unforgettable memories.
Based on our own experience, here are 7 things to know when you win a holiday competition.

1. Check it’s not a scam
Sad to say, competition scams on social media seem to be on the increase.
But, if you’ve followed our tips for entering, and done your homework, this shouldn’t happen to you.
But, better safe than sorry, you do need to do a bit of checking.
This is especially relevant if your notification came via a social media message.
Never click on any links, even if you’re sure they’re genuine.
Instead, contact the promoter by phone or email to double-check you have really won, and what the prize is.
Reputable companies will always follow up with some form of written confirmation.
And that takes you to step number 2.
2. Read the small print
Our mantra when entering competitions is ‘always read the Ts & Cs’ as most companies will make the prize details very clear.

But, let’s face it, we can’t remember everything for every competition we enter.
So this is the time to look closely and make sure that you meet the criteria they set (age restrictions, how many people it’s for, available dates etc.)
If you don’t, they may still honour your win, but don’t assume they will.
That said, do make sure in any follow-up conversations you have with the promoter that you know exactly what the prize is and what it includes.
We did have to challenge one prize supplier, trying to get us to settle for a lesser level of accommodation than the prize stated.
We stuck to our guns and, by being flexible on the choice of resort hotel and travel dates, and with the help of the promoter, we finally spent a fabulous family week in a Club Level room at the Hard Rock Hotel in Orlando with theme park entrance.

In our experience, quibbles like this are rare, and most of our wins have been exactly as advertised.
3. Get insurance
It’s unlikely travel insurance is included for holiday wins, especially if the trip involves activities like skiing, scuba-diving etc.
As soon as you have your prize holiday dates confirmed, get the best travel insurance you can afford for everyone in your party. If your trip is cancelled, you may not be entitled to a payout, as it was free, but you will still be entitled to recompense for delays, lost luggage, and any medical care you (hopefully won’t) need.
4. Check the extras
This goes back to number 1, check the small print (preferably before you enter) so there are no cost surprises.
Gratuities, transport to and from airports, drinks and other sundries are unlikely to be included, so you will need to budget for them.
Flights or train fares to and from the prize destination are sometimes included, but often not.
Local taxes aren’t something we’re used to in the UK, but many countries have additional charges for overnight stays. They’re not usually a lot, and sometimes included, but you do need to know about them in advance so when you’re presented with a bill at the end of your winning stay, it doesn’t sour the experience.
5. Check entry requirements
If you’ve won a prize in your home country, you can skip this part, but for most of us, a trip abroad is what we hope for. It’s certainly why we keep entering competitions and have done for more than 20 years!
And of course, as Dylan famously said, ‘The times they are a-changing’ for foreign travel. So now is the time to wise-up.
The best and most trusted source of information for travel from the UK is the Government’s Foreign Travel Advice website. There you will find everything you need from entry requirements to health advice.
Another useful source of government travel information is the Travel Aware campaign.
This is especially important for any vaccinations that may be needed, as these will have to be arranged, and sometimes paid for, in advance.
Having run our holiday competitions list page for several years, we know most of the prize destinations are for the UK, Europe, the Caribbean, the Maldives, Australia, USA and Canada, so here’s a summary of the latest requirements for these destinations.
Travelling to Europe

Across the Schengen area, travel is straightforward, but a little more time-consuming at arrivals and departures for UK residents than it used to be.
The European Travel and Information System (ETIAS), originally planned for 2023, is still not in operation and a start date has not been confirmed.
Once in place it will speed things up at Border Control for residents of many countries as long as they have applied, and paid for, an ETIAS waiver in advance.
When it’s in operation, airports will install smart passport gates, which mean you only have to look into a camera for facial recognition not scan your passport, although you will still need a physical passport to travel.
You can keep up to date with the implementation schedule on the official ETIAS site.
Travelling to the Caribbean

Okay, with 16 independent countries within the area, it’s hard to generalise.
Most UK tourists don’t need a visa, but passports should have at least six months left to run and blank pages for entry and exit stamps.
However, as always, there are a few exceptions.
The Cayman Islands, where a visa may be required
Cuba, which requires a tourist card available via the Cuban Embassy in London
Travel is not currently advised to Haiti, so it’s unlikely to crop up as a prize!
Travelling to the Maldives
You will get a 30-day tourist visa on arrival, there is no need to apply in advance.
There is a fairly extensive list of medical conditions to check before you go, but for the vast majority of UK travellers, very few vaccinations and certificates are required.
Travelling to Australia
You do need a visa to enter the country as a tourist, but apply for the free eVISITOR pass, and you can stay for up to 3 months. Other visas are available for longer or multiple visits, just in case you’re interested in a return trip after your prize holiday!
Full details of conditions and eligibility on the official eVISITOR website.
Travelling to America

You will have to have either an Electronic System for Travel Authorisation (ESTA) visa waiver or a full visa to enter or travel through the USA as a visitor.
ESTAs in 2024 are $21 but make sure you use the official US Homeland Security website to apply, or you may find you’re charged more.
Travelling to Canada
Similar to the USA, you will need an Electronic Travel Authorisation (eTA) for tourist trips of up to six months.
In 2024 the cost is $7 and again, make sure you use the official site.
6. Check your passport NOW!
Everyone, regardless of nationality or destination, should check their passports regularly.
It’s amazing how quickly time flies and they run out!
You can apply for a new one or renew an existing one on the official UK government site
But once again, be sure your passport meets the requirements of entry to your prize destination.

Pay particular attention to the issue date, not just the expiry date, as this is what’s checked on entering most countries.
You can read here about how some UK passport holders have been caught out.
7. Say Thank You
It’s amazing how few people do this, but we think it’s essential. You’ve won a prize, and a few words of thanks to the promoter and prize-giver never go amiss. It’ll give them a warm, fuzzy feeling.
Once you’ve had your holiday, why not let them know how it was.
If you have social media, tag them in your pictures.
For one of our family holiday wins, long before the rise of the internet, we actually created a mock newsletter with pictures and text of our winning week.
They loved it.
So from prize to paradise – pack your bags with purpose, now you know what to do after winning a holiday.
The 7 things to know when you win a holiday competition, in brief
1. Check it’s not a scam
2. Read the small print
3. Get insurance
4. Check the extras
5. Check the entry requirements (UK residents)
6. Check your passport/apply for one NOW (UK residents)
7. Say thank you
Where to next?
• Fabulous worldwide film locations
• How to avoid holiday rip-offs
• How to avoid holiday car rental mistakes