Travel Contest Tips – Win Free Trips and Goodies

I have been fortunate to have won some contest prizes: small trips, travel prizes, and two cars (yes, two cars!). People tell me I am so lucky. When I ask them if they enter contests, the most common response is, “No, I will never win.”

Cannot argue with that logic. If you do not enter contests, you have no chance of winning. The Great One, Wayne Gretzky said, “You miss 100% of the shots you don’t take.”

By no means am I a contest expert. I just wanted to share some tips I have learned. Perhaps one of your 2011 resolutions will be to enter a few contests. You never know what will happen.

  1. You must enter a contest to have any chance of winning it. Obvious but I will restate it.
  2. Contest versus sweepstakes. A sweepstakes selects a random winner. A contest requires some skill. Both are usually called contests, as I do in this post. A true contest may require you to answer a question about the sponsor’s business or something about the prize, play a skill game (which might just be clicking a spin button), etc.
  3. I usually only enter single entry contests and sweeps. Contests (and sweeps) may let you enter daily, weekly, one time, unlimited times. I am not a professional contest enter-er and do not want to spend my time organizing daily entries. If a daily entry contest has an attractive prize–like 1,000,000 frequent flyer points or a Super Bowl trip–I might enter a few times. Inevitably, I forget about it after a couple of days.
  4. Local and regional contests offer better chances to win. I won my second car and a trip from local businesses. I won Chris Guillebeau’s “Become Your Own Travel Ninja” by commenting on a blog post.
  5. Read the rules. I won the second car by sending in a post card for a second chance opportunity. Yes, I was very lucky. Also, a half million other people could have qualified by doing the same thing and not chucking that piece of mail.
  6. Save time by finding a central contest listing spot. Instead of looking all over the Internet for travel contests, I visit There are countless other contest and sweeps websites.
  7. Winners can negotiate the prize value. When you win a prize (I know you will!), determine if the listed value is overinflated. I won a two night resort stay value at $1300. When I ready to make a reservation, the daily room rates were around $100, with the most expensive room at $249. I thanked the prize sponsor but said that my tax liability was more than the prize value. I was ready to decline the prize. Instead the prize sponsor revalued the prize at $700 and reserved a phenomenal suite for me.

Feeling lucky? Perhaps these tips help inspire you to enter a few extra contests in 2011. If you win, let me know. If you have other contest tips to share, let everyone know by submitting a comment.

By the way, about those two cars. One was a “classic car” won in a national contest. Basically, it was a junker car with a fancy paint job. I had to desludge the engine the day after I took ownership. Anyway, it was a great car but by no means a new car or restored one. The other car was a base model car with no extras. I applied the contest value to the value of a new car. Yes, it was free money and I was fortunate to win.

No, I have not won a lottery. Maybe 2011 is the year!

Happy travels and best wishes for a lucky 2011.

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