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

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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 travel 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.


I haven’t talked about this much before, but I like entering travel contests. I love entering contests because I’ve won a few of them (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 most significant win was an all-expense paid trip to New Orleans.

Am I Lucky?

Although I’ve won a few travel 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 something because the contest evaluated me on a skill (usually writing). In those instances, my contest entry was judged as the strongest one. A couple of times  I “won” a prize 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).

How About Actually Entering 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 travel 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 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 travel contests to enter.

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 travel 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 traveller. 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 depend on a skill then take the time to send 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. I know my 80-year-old grandmother won’t be interested in a trip to Las Vegas, but my 30-year-old cousin might.

Make sure to check the terms and conditions to see if sharing will increase your 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.

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 specified 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 essential. 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.

Why You Should Read The Fine Print for Contests

Once upon a time, there was a traveller 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 particular liquor brand was holding a contest to win a weekend trip to New Orleans. The website said you had to buy a specially marked bottle 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. There 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 fantastic time she would have in New Orleans when she won this trip. A few weeks later she got an email telling she had won the trip for two to New Orleans from this contest. 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.

New Orleans Cemetery.

When I won the trip to New Orleans, my friend 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 an excellent tour.

So yes entering contests and making sure you read the rules and regulations is a good thing.

I hope you can put some of these tips to use to help you win some travel contests. Next in this series is the post Mistakes to Avoid When Entering Travel Contests.


Have you won any travel contests?

8 comments on “Tips for Winning Travel Contests Part 1 | Which Contests to Enter

  1. 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.

    • 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.

  2. Great tips and opinion for those wanting to get involved and enter such competitions. I am sure this article will help guide people down the right path to victory

  3. There are some great tips, and I think some apply to not just travel contest but any lucky draw or contests. After all, if you want to win, at least you have to be in the game. Thanks for sharing with us! @knycx.journeying

  4. Very interesting post! I fall into that category of why should I waste my time, but I like your tips and may reconsider if it is something that I really want or like. I agree wholeheartedly with the tip to do blog hosted giveaways/contests. The odds just seem better with those, right?

  5. I have never participated in a travel contest before but they always tempt me. Love the mention to the law of attraction and keeping a positive attitude! Maybe I’ll give one a shot sometime soon :).

  6. Whenever I hold a contest or giveaway on my blog, I always wish all my friends would enter. They just don’t realize how few people really enter, and how good the odds are that they could win. It’s way more fun to be able to offer a prize to someone I know, but I’m always fair and choose the winner by random drawing! Good tips, by the way — and so cool that you’ve won some great prizes!

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