Tips for Winning Travel Contests Part 1 | Which Contests to Enter

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.

This isn’t something I’ve talked before on this platform, but I like entering travel contests. I probably like entering contests because I’ve won a few (about 20 or so, though I’ve stopped keeping track). The prizes I’ve gotten have been as small as a free app for my smartphone to free hotel stays. My biggest score was an all-expense paid trip to New Orleans.

Even though I’ve won a few contests I am not luckier than anyone else. My name was just randomly drawn for some of the contests I entered. In a few cases I won a contest because I was evaluated on a skill (usually writing), and some people thought my contest entry was the strongest one submitted. In a couple circumstances I won something because I was one of the first people to comment on a specific blog post that was giving away a prize. Yes, sometimes winning is that easy. Here are my other tips.

Actually Enter Contests

This might sound silly and obvious, but sometimes we overlook these simple things. Some people might have a defeatist attitude when it comes to contests. Why bother trying ? I’ll never win. They don’t enter the contest, which means obviously they won’t win the contest. Don’t have that attitude. Actually go ahead and have that attitude if you want. The fewer contests you enter the better chance I have of winning, right?

I do believe in having a positive attitude. Maybe you can call it the law of attraction or whatnot, but I think what you put out is what you get back. When you enter a contest don’t put out a negative “I’ll never win attitude.” Be positive and hopeful. You’re entering a contest. You’re not getting a root canal. This should be fun. For my fellow Canadians Contest Canada has a good selection of contests to enter, including travel contest.

Street in London, UK.

I love entering travel contests. Recently I won an apartment stay in London.

Enter Contests With Better Odds of Winning

I’m horrible at math, but I know I have better odds winning a contest with a 1 in 10 chance of winning than a contest with a 1 in 1,000,000 chance of winning. I like entering blog hosted contests because they’re usually smaller contests with better odds of winning. Of course better odds of winning doesn’t guarantee a win, and I have entered (and won) larger contests too. No matter the odds the worst thing that can happen is that I won’t win, and then I am no worse off than before.

Enter Contests You Want To Win

I’m not an adventure sports traveler. A contest to win a week of rock climbing and camping doesn’t sound like my idea of fun. If the prize doesn’t appeal to you then don’t enter the contest. With contests most prizes can’t be transferred or sold. Entering contests that you don’t want to win only decreases the odds of winning for the people who do want that prize.

Take Time Entering Contest When Necessary

Some contests you just have to fill out a form with your basic information (name, age, etc) and maybe enter a skill-testing question (in Canada at least). Other contests you might also have to write a story, submit a photo, or a video or show some other skill/talent. If the odds of winning depends on a skill that you’ll be evaluated on then take the time to submit the best entry you can.

Use Social Media When Needed

Some contests will give you extra entries for sharing your contest entries on social media. Just be careful not to constantly bombard your followers with contest information. One trick I use to overwhelm my Facebook friends with contest information is I’ll share different contests with specific friends who might be interested in it. My 80 year old grandmother isn’t going to be interested in a trip to Las Vegas, but my 30 year old cousin might be.

Make sure to check the terms and conditions to see if sharing will increase you odds of winning. Sometimes a sharing Facebook or Twitter sharing box will pop up after you submit a contest entry online, but if you check the rules sharing the contest won’t increase your chances of winning. If that’s the case I’ll only share that contest if it’s something my followers would be interested in.

Keep Track Of The Contests You Enter

You might not like creating spreadsheets as much as I do, but I have a spreadsheet where I keep track of what contests I’ve entered, when I entered, and when the contest ends. Furthermore I have contests where I can enter daily separated from contests limited to one-time entries. Keeping track of the contests you’ve entered won’t give you better odds of winning, but it can prevent you from accidentally entering a contest multiple times. With some contests you may be limited to one entry so entering multiple times, even by accident, could void your entry all together.

Yes. I am a nerd.

Read The Rules

Yes, reading the rules is boring, but you want to make sure you are legally allowed to enter the contest. You want to know when the contest ends, how many times you’re allowed to enter, and if there are other restrictions (for example some contests allow only one entry per household, not per person). Other things you’ll want to find out would be when the draw date for the prize is, how winners will be contacted, how much time prize winners have to claim their prize, and if there are conditions are attached to the prize. Reading the rules is boring, but it’s important.

A Short Story on Why You Should Read The Fine Print for Contests

Once upon a time there was a traveler named Alouise who fell in love with the city of New Orleans when she went there in June 2012. She was sad when she had to come home, and knew she would have to go back to the city again. One day she saw a certain liquor brand was holding a contest to win a weekend trip to New Orleans. The website said you had to purchase any specially marked bottles of said liquor brand to get a pin number. Then you could use the pin to enter an online form to win a trip to New Orleans.

Alouise never had this particular type of liquor before. She didn’t want to buy a bunch of liquor she might not like, even for the chance spend a weekend in one of her favourite cities. So she decided to read the contest rules. Wondrous news appeared when she learned she wouldn’t have to make a purchase. All she would need to do is send an email to the contest organizer to request a pin for a contest entry.

Alouise sent an email to the contest organizer requesting a pin for the New Orleans contest. Within a day she received a response and a pin number. Excitedly she enter the pin number into the online contest form, and thought about the amazing time she would have in New Orleans when she won this trip. A few weeks later she got a fantastic email telling she had won the trip for two to New Orleans. While the trip was very short (there was only 36 hours in New Orleans) and she was exhausted when she got home she had a great time, and was excited she got to back to a city she loved. Alouise was very glad she read the fine print and decided to enter the contest. If she hadn’t she would have never got the chance to go back to one of her favourite cities for free. The end.

Save our Cemeteries Tour in New Orleans

I took a friend with me to New Orleans and she really wanted to do a cemetery tour. This is one we did with Save Our Cemeteries a volunteer-based organization committed to preserving and restoring cemeteries in New Orleans. It was a great tour.

Hopefully you’ll be able to put some of these tips to use to help you win some travel contests. Coming up in the second part of this series I’ll talk about some of the mistakes you should avoid when entering travel contests.

Things You Should Know

This post has not been sponsored or endorsed by any particular organisation or brand. All views and opinions in this post are my own.
If anyone is interested the hotel I stayed in New Orleans was The Blake Hotel in the Central Business District.

Have you won any travel contests?

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One Response to Tips for Winning Travel Contests Part 1 | Which Contests to Enter

  1. Ryan Biddulph August 2, 2017 at 7:33 AM #

    I like your tips Alouise. Timely too as I just entered a digital nomad contest a few hours ago. Free trip, 3 weeks, all expenses paid, and the 3 locations are super close to New Jersey which is key these days because I want to be close to home. Good note on actually wanting to win these too. I caught myself a few times when about to enter cool-sounding contests that actually were not up my alley. Gotta have your energy right to align with the win.

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