I don’t like the term lucky. It makes it seem like we have no control over our lives, and I don’t believe that’s true. Sometimes though a person can luck out with certain opportunities, like how I got a message a couple months ago from Beers and Beans that I won a travel contest they had. The prize, a $100 Roomorama voucher. This is the fifth contest I’ve won in the past year and a half. My other recent prize winnings:
- A $200 Hotels Combined voucher from a contest on A Dangerous Business. I used that prize to stay in Victoria, BC.
- A Moleskine travel journal from a contest on Tend To Travel.
- A $50 Urban Adventures Voucher for the Blog Your Backyard Contest. I’ll be taking a Pub Crawl tour in Houston with this prize.
- A Camelbak backpack from a contest on Adventurous Kate.
So what is my secret to winning? First let me go over what I didn’t do to win these contests.
- I did not consult the services of a psychic, medium, tarot card reader, palm reader, numerologist, or any other person/organization/group to win.
- I did not pay any money to increase my odds to win.
- I did not use a lucky penny, four-leaf clover, rabbit’s foot (eww), or another lucky charm to win.
- I did not bribe the companies or the contest owners to win (that’s usually against contest rules).

The bed in my suite at The Helm’s Inn in Victoria. Just one prize from one of the contests I’ve won.
With that out of the way what did I do? What is my amazing, earth shattering, life changing, space-time continuum altering, secret to winning?
I entered. That might seem like a given, but it’s really the most important step. I like to say, “you got to be in it to win it.” A little cheesy, but it’s true.
Here are some other tactics I’ve used. Of course none of these are guarantees to winning a contest, but I don’t think using them hurt my chances.
- I entered contests where I had better odds of winning. I am not a math person, so I’m not going to try and learn everything there is to know about random numbers and the laws of probability. I do understand that a smaller contest, with say a 1 in 10 chance of winning, will give me better odds of winning than entering a contest with a 1 in 1,000,000 chance of winning. Often blogs will have small contests with better odds of winning. Of course that’s not to say you’re guaranteed to win a smaller contest, or that you can’t win a larger contest, it’s just your odds of winning a smaller contest is greater than winning a larger contest.
- I only entered contests with prizes I wanted to win. A prize with a week of surfing school in Hawaii might sound nice to some (and granted I would want to go to Hawaii) but I can’t swim (at all) and so surfing lessons would really just be a waste for me. Many contests have a rule where you can’t trade or sell off your prize, so why waste your time and enter a contest with a prize you don’t want or need? Plus entering contests just to win something you don’t want just decreases the odds of winning for those who enter and want the prize.
- I only entered contests I could win. As a Canadian there are a lot of US based contests that I can’t enter. It’s just a waste of time to try and enter a contest that isn’t available to you. Even if you did win, you’re entry would be discarded and you wouldn’t get the prize.
- I took my time entering when necessary. There are some contests where all you have to do is enter your basic information (name, age, etc) and maybe enter a skill-testing question (in Canada at least). There are other contests where you have to answer a question, maybe write a story, submit a photo or a video. If your odds of winning depend on a skill you’ll be evaluated on you should take the time to submit the best entry you can.
- I used social media when the contest asked for it. My mother doesn’t have a Facebook account, or a Twitter account. She thinks they’re a waste of time, and well they can be, but there a lot of contests that require social media accounts just to enter. Having Facebook and Twitter especially can help increase your odds of being able to just enter certain contests.
- I check websites that have free contest listings, like Free Travel Contests, just like its name implies it lists free travel contests. I also subscribe to a lot of travel blogs that have free travel contests. Subscribe to a wide variety of blogs and do a search in your RSS reader for terms like contest, giveaway, and freebie to see if there’s a blog sponsored contest you can enter.
Every country will have their own laws about the differences (if any) between a contest, sweepstakes, and a lottery. Make sure you know your country’s rules, because you don’t want to get ripped off by contest scams. Don’t give out your credit card info, bank account info, or anything else that seems suspicious. Never wire or transfer money to enter a contest. A contest should be *free to enter. While, depending on your country’s rules, you may have to pay taxes on your prize you shouldn’t have to pay any money up front to claim a prize. Unfortunately there are scammers out there so it’s important to be informed about what’s legitimate and what is not. Know the rules for entering and winning contests in your country, and read the contest rules carefully. Usually travel contests have pretty amazing prizes, but if it sounds way to good to be true then it just might be.
*There are legitimate contests with payments that support charities such as Passports with Purpose. With these contests your payment is actually a donation you make to a charity, and you have the choice of putting your name in for a contest draw, in addition to your donation. PWP is a great charity organization, completely legitimate, but even with a paid contest there should be a way of letting you enter the sweepstakes without purchase. I think that entering a sweepstakes like this and not making a donation defeats the purpose, and I’d imagine there’d be some negative karma heading your way if you won a prize, and didn’t make a donation. Still if it’s a legitimate contest you should be able to enter for free without purchase.
I wouldn’t rely on winning contests to be your only way of traveling, but entering free travel contests could help you with your travels if you win. Enter a contest, and who knows what might happen.
Update April 3, 2013: since originally publishing this post I’ve won several contests including a week car rental from CarRentals.Co.UK and Wild Junket Magazine, a set of business cards from ArtOfBackPacking and Uprinting, a one-night stay at Radisson Hotels from The Planet D,, a series of DK Eyewitness Guides from The Traveling Canucks and an all-expense paid weekend trip to New Orleans with Southern Comfort.
Despite what it may seem this isn’t a sponsored post, although I am definitely grateful to all the companies, bloggers, and others persons who’ve given me such great prizes. Please note the advice in this post may or may not be applicable to all contest situations, and that Traveler Ahoy and myself lay not claim in guaranteeing that you will necessarily win contests, sweepstakes and/or lotteries using the methods described within this post.











excellent tips. I once won satellite Tv for three years when I was 8. I did the spot the difference in the local newspaper. Made me very popular with my parents. You’ve inspired me to re-enter the game.
What I don’t like about contests is that it’s a lot of promotion to be done on behalf of who’s running it. The first thing usually is sharing the fact of entering with my friends on Facebook. I know this is publicity they want but I don’t see how it can be interesting to my friends, really.
Thanks for the comment. You bring up a good point. A lot of contests have heavy promotions, but read the fine print carefully. Sometimes the telling your friends on Facebook is just option that people click anyways. I try not to overwhelm my social media accounts with contest information because it can get to be too much.
Very few do that because you earn points for sharing, points for commenting, points fr subscribing to their newsletter, etc. The more points-the more chance to win.
Very true. Most of the contests I’ve won haven’t had too much social media bombardment, a like on Facebook, a follow on Twitter, and maybe a Tweet. If a Facebook contest is run via an app you can set it so that you are the only person who sees posts from the contest. Usually though these are for bigger contests with smaller odds of winning.
I definitely recommend finding small competitions to win. I’ve won three things this year which has been REALLY exciting – flights to Amsterdam, a tour from Zanzibar to Nairobi and a holiday to Egypt. Been a bit crazy and all my friends hate me now
Wow. You’ve done really well for yourself. Congrats on all your wins.
You are very lucky, I rarely win anything and I swear I`m entering!
Thanks for the comment. Rarely winning a contest is still better than not winning. Keep entering and who knows what could happen.
I love that you’ve made winning your thing!!!!
Thanks for the comment. I love that you think winning is my thing. I hope it can be your thing as well.
Ohhh, thanks so much for the link to the Free Travel Contests site!! Great tips, you are so right (clearly, given your successes!!)!
Thanks for the comment. I figure with everything I’ve won recently I better spread the karma and help some other people win too.
Those are really good tips! Congrats on winning all of these contests. I didn’t know about the Free Travel Contests site. However, I think I am going to ban you from the contests I have coming up in the future!
What a fun post and I’ll be checking out that site too. This year I have won two books – one a Thai cookbook and one was an excellent read about hiking in Europe. Not a lot but the entering was easy. And I went to the Calgary outdoor show and won a $500 coupon off a trip to Laidman Lodge – which I’m using that this summer.
Thanks for the comment Leigh. You bring up a good point about contests at trade shows. There was one in Edmonton for travel around Alberta and they had a ton of contests that were really easy to enter. Congrats on your wins. I’m sure you’ll really enjoy your trip to Laidman Lodge.
i think the most I have ever won in my whole life is a hairdryer. Luck just never seems to be on my side. Well done on your run
Thanks. The most I ever won before this was a book in grade school, so your luck can definitely change.
I never enter contests, but I did win 2 round-trip business class tickets on AirTran a few years ago after buying raffle tickets. Best $20 I ever spent! I’ll be checking out the Free Travel Contests site for sure. Thanks for the tip!
That does sound like a great deal. I don’t usually go for lotteries, but I don’t mind supporting raffles for a good cause.
Loved it. Interesting and now I want to join all the new contests:)
You should definitely enter contest. You never know what might happen.
Hahaha, love this! And so true. Reminds me of that joke about the dude praying to win the lottery, and then god answers with, “Well buy a ticket!” Har har.
Very funny. I’m very much a realist, but still a part of me dreams about winning the lottery.
I think the most important to fill your information, as a lot of people are saying any contests, but how you can win something if you even didn’t enter that contest
Yep. Wishful thinking only goes so far. You can’t win if you don’t enter.