8 Great Contest Tips – How I Won Cars, Trips, and more!

Here are some of my favorite contest tips, with a particular focus on increasing your odds to win travel contests.

I have been fortunate to win some amazing contest prizes—trips, travel prizes, and two cars (yes, two cars!).

People say I am so lucky. But when I ask 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 will never win.

Wayne Gretzky, The Great One, said, “You miss 100% of the shots you don’t take.

Another favorite quote is from George Bernard Shaw: “People who say it cannot be done should not interrupt those who are doing it.

So, yes, you must actually enter a contest to have any chance to winning. That is my first tip. Good luck!

1. Enter a contest to have a chance to win

Do you see “Win a trip to Hawaii” and pass over it, thinking you will never win? Well, change that thinking. An obvious statement perhaps, but I must restate it. In order to win a trip contest—or any contest—you must actually enter the contest. The more contests you enter, the better chance you have of winning. Capisce?

2. Difference Between Contest and Sweepstakes

A sweepstakes selects a random winner. A contest requires some skill. 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.

Although most of the east entry contests are actually sweepstakes, for the sake of convenience, in this article I call both “contests.”

3. Focus on single entry contests

Contests (and sweeps) may let you enter daily, weekly, one time, unlimited times. I am not a serial contest enter-er. 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. Otherwise, I stick to “enter one time” contests.

4. Better chances to win local contests and blogs

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.

contest tips: the Funness Mobile was the second car I won in a contest
the Funness Mobile was the second car I won

5. Do not ignore large contests

I was amazed to win a trip to Hawaii in a Facebook contest, a free Caribbean resort stay and other prizes on Instagram, and a $500 travel voucher in a major Twitter chat. Yes, you can win Twitter contests—details in Finding Travel Deals in Twitter Chats.

6. Read Contest Rules

I won that second car by mailing in a postcard (remember them?) for a second chance opportunity. Yes, I was extraordinarily lucky. Also, hundreds of thousands of people could have qualified by doing the same thing and not chucking that piece of mail. Remember tip #1, you must actually enter a contest to have any chance of winning.

view from my hotel room in Hawaii
win a trip to Hawaii? Here is the view from my Kona hotel room

7. Find central contest listings

Sure, you can type “travel contests” into Google and find some on your own. Instead of scouring the Internet for travel contests, I click on the contest links in JohnnyJet’s weekly newsletter. Countless other websites list contests and sweeps so find the best source for you.

8. Negotiate contest prize values

When you win a prize—I know you will!—determine if the listed value is overinflated. I won a travel contest with a two night resort stay (with dinner) valued at $1,300. 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.

sitting room of my suite at The Greenbrier
win a trip in a local contest: sitting room in my suite at The Greenbrier resort WV

Feeling lucky? Perhaps these contest tips help inspire you to enter a few extra contests. If you win, let me know.

By the way, about those two cars.

One was a “classic car” from 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. Of course, it was a great car but by no means a new car or restored one.

first car I won in a contest
contest tips: first car I won in a contest

The second 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.

Both were fun cars for scenic drives.

No, I have not won MegaMillions or Powerball but perhaps it is time to win another car; it HAS been about 10 years.

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22 thoughts on “8 Great Contest Tips – How I Won Cars, Trips, and more!”

  1. A car that’s incredible i wouldn’t say I have won anything in my life. Ill have to start having a go again

  2. i really want to win something because I’m pretty much poor, my sister had cancer my brother almost died getting his tonsils out and my car got stolen and i need to pay all those bills to the hospital so i cant afford a new car and this would just make everything better it would give me hope if i won at least 1 thing. Thank You!!!!

  3. recently won 2 3-day VIP passes to our favorite music festival. I proposed to my gf the first night on stage with ehr favorite artist. Won the VIP’s on a facebook thread by Pedialyte. I “liked” the post, I commented, I used their hashtag (which wasnt required) and I went to Pedialytes webpage, liked the page, liked a couple of their posts, commented on multiple posts (all of which wasnt a requirement) and a few days later we won. Could have been random but I beleve being relevant in a contest sponsors algorithms might help your odds. Just a thought.

    btw getting on stae with my now fiancee also happened by me simply asking via email. Stay posi peeps.

  4. Being in it to win it is key Charles. I used to write off any contest, fearing odds stacked up against me. Now I join more though. Who knows? I feel it’s fun to join and if you win, even more fun. Nice rides dude.

  5. I have won gift certificates…most recently was my $50 one from McDonalds, free tickets to see the Black Eye Peas and a few others. I have recently started back. Wish me luck. Best advice I can give is enter local contest or ones that have a limited amount of states for people to enter and small amount of time to enter. It betters your chances of winning.

  6. I have entered about 15-25 contests every day for 8 years and have not ONCE! Almost every contest with a trip for the prize, the winner was a professional travel writer,i kid you not.I think they are all fixed or fake.

  7. Great post! I’ve not won contests per se but have won many travel items from Twitter – a few $50 gift cards to Nordstrom, cruise swag (robe and stuff), $250 Expedia voucher for a photo they used, 40k Intercontinebtal points (used in Johannesburg as part of safari trip) and a two night stay in Sydney at the Pullman hotel which gave me a great reason to plan a RTW trip.

    Most involved participating in a chat, a retweet or submitting a photo. I could use a new car so going to invest in some postcards!

  8. This is a cool post! I had no idea you were such a lucky person… or at least that you were smart enough to take advantage of opportunities to be lucky 🙂

  9. Awesome stuff. A ninja indeed. Remember the Smokies always have a spot for you and yours!Truly my very best wishes,

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