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Tips for Winning Travel Contests Part 2 – Mistakes to Avoid

This is the final installment of the two-part series about Tips for Winning Travel Contests. Read Tips for Winning Travel Contests Part 1 – Which Contests to Enter here.

Disclaimer: While this post has advice about entering travel contests it is for informational purposes only. I assume no responsibility or liability for any action you choose to take or not take because of this post. Aside from winning one legitimate charity raffle (Passports With Purpose) all contests I’ve entered and won have been contests that are free to enter. If you have to “pay to enter” or make a purchase do some research and double check the contest you are entering is legitimate and not a scam. A legit contest should always have the option of entering without purchase.


In the first part of this series I talked about the contests I’ve won, which has been a good few. I also mentioned how it’s important to enter travel contests. Even if you don’t think you’ll win it’s always worth it to enter.

Well it’s actually not that straightforward. There are actually several contests I won’t enter, and there are a few mistakes you should avoid making when entering travel contests.

Tips for Winning Travel Contests – Mistakes to Avoid

The Mistake – Falling for Contest Scams

This mistake is at the top because in my opinion it is the most important rule. You don’t want to fall for contest scams. At best it’ll be a waste of your time. At the worst it could cost you a lot of money, and even your personal information/identity. Unfortunately there are contest scammers out there. These scams might look legitimate at first, but they’re not. They’re trying to get you to part with your money, and sometimes even personal information (like your passport or credit card number, which could be used in identity theft). Here are some things to help you decide if a contest is legitimate or not.

    • Is the company/brand hosting the contest a legitimate company? Is it one you’ve heard of before? Have they been around a while? That’s not to say a new company/brand can’t host a travel contest, but if suddenly there’s a company/brand that comes out of nowhere and is hosting a contest with some amazing luxury vacation prize it could be a bit of a red flag. Do some more research.
    • Similarly to the first point, are the prize sponsors legitimate companies? Are the companies ones you’re familiar with or have heard of yourself? Have they been around a while. If a contest seems to be run by a company/brand you’ve never heard of with a vacation prize from a company you’ve never heard of it very well could be a scam.
    • Are they asking for money, bank, or credit card details? If they are this is very likely a scam. Now I should say there are charity raffles where you can donate money in exchange for a raffle ticket or entry into a contest. This is what I did a few years back with Passports with Purpose (a great yearly travel charity fundraiser, which has since ended). I made a few $20 entries and won a $500 travel voucher. However the difference between a charity raffle/fundraiser and a scam is that the charity will be registered in the country it’s in, and you should (depending on your country’s laws) be able to get a tax deductible receipt for your donation. If it’s not a registered charity and a legitimate company then you should not pay anything for a chance to win. Even in a contest where it says you need to make a purchase there should be a way to enter without making a purchase (like the trip I won to New Orleans).
    • Are they asking for too much information? Asking for your name, contact email and/phone, and maybe your home address is legitimate. They may need you to confirm (usually by checking a box) that you’re the age of majority (particularly if the contest is hosted by alcohol brand). Maybe you’ll have to enter a skill testing question to prove you’re a person and not a robot. If a contest asks you for your ID, passport, bank/personal finance information (as mentioned before) or any other personal information be wary. While you may need to provide passport information to claim a prize involving international travel you shouldn’t need your passport just to enter a contest.
    • Is something else off? Are you getting a weird, gut feeling not to enter? Did you “win” a contest you don’t recall entering? I always think it’s best to trust your intuition. If something seems weird then don’t enter, or at least do some more research first.

These are just a few things to lookout for in regards to possible contest scams. While it’s geared to American readers the About Contest page is a great resource for contest scams. If you think a contest is scam contact your local police department to report your suspicions. Help other people by putting the scam to an end.

Las Vegas, Nevada

The Mistake – Entering with an Automatic Form

Most travel contests I enter are online and the entry forms are pretty easy to complete. Many just require some basic information like your name and contact details (usually phone number/email and sometimes an address). When you’re entering multiple contests a day it can be a bit of an annoyance to retype the same information over and over. You might think about using an auto-fill program (like Google Chrome has) to make entering your contests easy.

I’d caution against using autofills. Many times if you check the contest rules/regulations using automatic entry programs, including autofills are against the contest rules. If you use these programs when they’re not allowed you’re basically voiding your entry and wasting your time. If the contest prohibits autofills or any other sort of automatic entry make sure to type everything in the old fashion way so your entry will not be in valid.

The Mistake – Entering Popularity Contests

You’ve probably seen these contests, where you have to get people to vote for your photo/video/tweet/writing, etc. These contests are a pain to enter and annoying to see because you’ll often see people overwhelming their friends, family and complete strangers with “Vote for Me!” pleads on social media. I never liked popularity contests in High School, and they’re just as annoying to me now.

Now that’s not to say you can’t enter popularity or voting contests, just be cognizant of how many you’re entering and how often your begging your friends/family/colleagues/that guy you met at a college party once ten years ago/random strangers to vote for you to win a trip to Hawaii. Don’t be spamming (for lack of a better term) the same people over and over and over again.

The Mistake – Not Knowing Your Talents/Skills

There are some contests where the winner is picked based on a skill or talent, rather than being randomly selected. It helps to know what your skills are and where you should spend your time entering contests. As an example I’m not a videographer so I’ll skip over contests where you have to make a video essay to win. It just doesn’t make sense for me to spend time entering a contest with a skill or talent I’m not that good at (yet). Now writing contests I will enter, and I have won a few travel writing contests before.

The way I think about skill-based contests is like this, am I okay with spending my time on creating this entry even if I don’t win? Basically if the contest is for a skill or talent I have or one I’d like to spend time developing (and if the contest isn’t a scam and I actually want to win the prize) then I’m okay with entering a skill based contest. Or take it like this. I’m a writer, so I like entering writing contests because it helps me develop my skills. Even if I don’t win anything I feel the time spent honing and developing my writing is worth it. I’m not a graphic designer, and I don’t have any desire to be a graphic designer. Entering a contest where I have to create a graphic design is just wasting my time because I don’t have that talent and it’s not something I have a desire to develop.

The Mistake – Entering Complicated Contests

Filling out a form, maybe sharing a contest on social media is one thing, but I only have so much time in a day (I have other things to do aside from entering contests). If a contest is really complicated to enter then I probably won’t enter it (unless the prize is amazing and worth the extra effort). One time I saw a contest where you filled out an entry form and then only if you referred a friend to the contest, and they referred another friend would your original entry get counted. It was like the pyramid scheme of contests. Not worth it. Entering and winning contests is fun, but you still need to live your life.

The British Columbia Legislature in Victoria

The Mistake – Not Knowing BEDMAS

All right so this rule might just be for my fellow Canadians. See in Canada contests have to have a skill testing question for people to answer. This usually takes the form of math question. I was never great at math, but I do remember the rule of BEDMAS from entering so many contests. That is first you do anything in Brackets, then any exponents (which I haven’t seen in contests, but it could happen), then any multiplication or division (whatever is first on the left), and then any addition/subtraction (again whatever is first on the left). BEDMAS is acronym to help you remember this rule.

So 2+10X100 = 1002. You do the multiplication of 10X100 first, then the addition of +2. Or take (15÷3)x13+7 = 72. First you do the bracket (which gives you 5). Then you multiply that by 13 (giving you 65) and then you add 7 giving the final answer of 72.

I can’t believe I just did two math problems on my travel blog and explained a math rule. I hate math, but to win a contest I’ll do some math. To be honest though most skill testing questions are pretty simple 2+2 sort of thing.

The Mistake – Enter Contests with Unrealistic Travel Expectations

There will always be travel restrictions on the prize. Depending on where you live you might have to pay taxes and fees, so you’ll have to decide if the prize is worth taking. One time I saw a contest to win a trip to Costa Rica. Sounds great, right? Well the prize only included airfare from Miami. If I entered I’d need to pay my own airfare (about $800 at the time) for a last minute flight to Miami, which was something I couldn’t afford at the time.

The Prize – Entering Contests You Can’t Win

This is something I’ve noticed now that I live in Ireland. There are contests here that I can’t enter because I’m not an Irish citizen. Yet there are contests with sponsors back home in Canada that I can’t enter right now either, because either the prize is back in Canada or I’d have to be in Canada to claim the prize. This is one reason why I like entering online contests because many (not all) are open to citizens world wide. I also like entering contests where the prize is a voucher for a hotel or airline rather than a trip itself. With a hotel voucher you can usually use it in a variety of locations. If you win a trip/vacation somewhere then you’ve got more restrictions on where/when you can use your prize.

This Mistake – Not Checking Your Email or Phone

When you enter a contest the rules will tell you when and how they will be contacting the winner. I have a secondary email (to prevent my main emails from being inundated with contest sponsor emails) to enter contests. Even still I remember to check my contest email every day. If you’re contacted as a winner make sure to respond right away, because if you wait too long then you might be disqualified and they’ll have to choose another winner. You don’t want to mess up that.

The Mistake – Not Having a Passport

When I won that trip to New Orleans it was for 2 people, so I called a friend and asked if she wanted to come with me. Of course she said yes, but the problem was her Passport had expired. We had to show we had a valid passport for international travel (since we were flying from Canada) to claim the prize, so my friend had to pay for a rush passport. It was a tight squeeze, but she managed to get it just in time. If you’re entering travel contests I’d recommend getting a valid passport ahead of time. Actually you should just always have a passport because it’s a great incentive to help you travel.

The Mistake – Only Entering Travel Contests

I’ve focused on travel contests because I love traveling, but that’s not to say those are the only contests you should enter. I have a friend who loves going to the movies and she always seems to be winning free movie tickets. If the prize is one you want, if the contest is legitimate, and if you are legally allowed to enter then go for it.


I hope this series has given you some information to help you enter contests, and has inspired you to enter a few contests for yourself.

Have you won any contests? Leave a comment below.

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