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

Disclaimer: This post 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 charity raffle all contests I’ve entered have been free to enter. If you have to “pay to enter” or buy something do some research. Check that the contest is legitimate and not a scam. A legit contest should always have the option of entering without a purchase.

This isn’t something I’ve talked before on this platform, but I like entering travel contests. I 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.

Am I Just Lucky?

Although I’ve won a few contests I am not luckier than anyone else. My name was randomly drawn for some of the contests I entered. In a few cases I won a contest because the contest evaluated me on a skill (usually writing). In those cases someone judged my contest entry as the strongest one. In a couple circumstances I won something because I was the first person to comment on a blog post. Yes, sometimes winning is that easy. Here are my tips to help you win travel contests (winning not guaranteed).

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 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. 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.

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. Still I know the odds of winning a contest with a 1 in 10 chance are better than a contest with a 1 in 1,000,000 chance. I like entering blog hosted contests. Why? 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 you usually are not able to transfer or sell the winning prize. Entering contests that you don’t want to win is pointless. You don’t want the prize and it decreases the odds of winning for the people who do want to win.

Take Time Entering Contest When Necessary

Some contests you fill out a form with your basic information (name, age, etc). You might need to 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 then take the time to submit the best entry you can.

Use Social Media When Needed

Some contests will give you entries for sharing your entry on social media. Be careful not to bombard your followers with contest information. I only share contests with people who will want the prize. My 80 year old grandmother won’t want to win 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. Often, 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 the prize is something I know someone will want.

Keep Track Of The Contests You Enter

You might not like creating spreadsheets as much as I do, but I have a contest spreadsheet. Here I keep track of what contests I’ve entered, when I entered, and when the contest ends. Furthermore I have daily entry contests separated from contests limited to one-time entry. Keeping track of the contests you’ve entered won’t give you better odds of winning. It can prevent you from entering a contest several times when it’s not allowed. If you enter a contest several times when it’s not allowed it could void your entries. Then you won’t win, and you’ve wasted your time.
Yes. I am a nerd.

Read The Rules

Yes, reading the rules is boring, but you want to make sure you are allowed (in a legal sense) to enter the contest. Find out the following
  • Can you enter the contest? Is it open to people in your country/state/province?
  • Do you need to be a specific age to enter (over 18 or 21). If you are underage and can enter do you need a parent’s permission
  • How often can you enter the contest?
  • Are there other limits to entering? Some contests are one entry per household, not per person.
  • When is the draw date for the prize?
  • How are winners contacted (by phone, email)?
  • How long do prize winners have to claim their prize? If you’re selected as a winner you may have to respond within a certain time period. If not the contest might have to pick another winner.
  • Are there conditions are the prize? Do you need to pay taxes or fees on the prize? Are travel dates (for travel prizes) restricted to a specific period?
Reading the rules is boring, but it’s important. You don’t want to waste time entering a contest you can’t win. Or worse enter a contest incorrectly and not be able to claim a prize if you win.

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

Once upon a time there was a traveler named Alouise. She 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 buy a 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. So she decided to read the contest rules. Wondrous news appeared when she learned she wouldn’t have to buy anything. 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. Excited she entered the pin number into the online contest form. She 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 (only 36 hours in New Orleans) she had a great time. She was happy 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 wanted to do a cemetery tour. This is one we did with Save Our Cemeteries a volunteer-based organization. They help to preserve and restore cemeteries in New Orleans. It was a great tour.

I hope you can put some of these tips to use to help you win some travel contests. Next in this series Mistakes to Avoid When Entering Travel Contests.
Things You Should Know

This post is not sponsored or endorsed by any particular organisation or brand. All views and opinions in this post are my own.
The hotel my friend and I stayed at in New Orleans was The Blake Hotel in the Central Business District. As it was part of the New Orleans prize I won the stay was free. The hotel was quite nice in a good central location.

Have you won any travel contests?


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2 Responses 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.

    • Alouise August 3, 2017 at 11:32 PM #

      That contest sounds like it’d be a great one to win. And yes I totally agree you gotta have your energy right to align, but I hate saying things like that cause it sounds a bit woo woo. But then again that woo woo has helped me win a few contests, so I can’t complain. Thanks for the comment Ryan.

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