How to Enter and Win Travel Contests

I’ve “won” six travel contests/sweepstakes. One allowed my husband and I to fly to Australia for 10 days, all on someone else’s dime. (Thank you yet again Australian Tourism, Delta Airlines, and most of all, Virgin Australia.) Two were the “lottery” for regular priced tickets at big sporting events (Final Four and Masters). One was a reduced price vacation to an all-inclusive in Cancun. One was frequent flyer points. The other was a runner-up t-shirt. Actually two t-shirts, in different sizes, presumably so that one would fit. 

Six wins in hundreds may not sound worth it, but you can’t win if you don’t play. And a few tips will help you enter the right contests and increase your odds to win travel contests! So I’ll tell you what I’ve learned about avoiding scams, finding and picking the right contests for you, and maximizing your time with a cleaner inbox.

Top Travel Contest Tip- Avoiding the Scams

If you read all the way through this and remember nothing else from this blog, remember these two things: A LEGITIMATE CONTEST WILL NOT ASK FOR TOO MUCH INFORMATION AND IT WILL HAVE OFFICIAL RULES. Standard travel contests will need, at minimum, your email address. Most will ask you for your name, your country of origin (if open to more than one country) and postal code. Later they will use this to verify who you are and that you in turn aren’t hustling them. The vast majority of contests will not ask you for your phone number, full mailing address, birth date, etc. Some contests may step you to a section where you might fill that out, but it’s likely for their own marketing purposes. You should be able to skip.

No legitimate contests will ask you for your payment information or social security up front.  You don’t want to enter or “win” travel contests that are pushing that from the entry. Scam! If you win, and the prize is big enough, you will eventually have to provide your social security number. This is legitimate for tax purposes and comes with some very official looking papers. What you win will be reported by the company to the IRS and will be counted as additional income in your taxes. (It’s a special earnings category and wasn’t nearly the dent we thought it would be.) 

If you win, you will get paperwork with official affidavits, contact information for the contest representative, and will have to provide copies of a legal ID and passport number if it’s an international trip. At this point if any concerns come up, you should be able to contact someone from the host company.  If these things are all true, congrats, you won a legitimate travel contest!

Quite simply, read the rules of each contest. Rules tell you if this is really a contest you want (see below). But they also show you if this is an honest contest, a scame, or a timeshare sell. A legitimate contest will describe eligibility to enter, how to enter, what the prize is, and all of the legal jargon that covers the company. Read the fine print. No surprises. (Or you can let me read the fine print for you by following Travel Your Bucket on Facebook!)

Is This Really a Travel Contest You Want to Win?

I can’t believe I’m saying this but not every trip is one you want. I’m not just talking about turning down an obviously dangerous or unappealing place. Not all trips are equal, even if the destination is appealing. For instance, two trips headline “Dream Trip to Italy.” But one’s small print is a fully paid trip to Italy. The other’s is four nights in Milan with a $500 air voucher. Can you afford the extra thousand or more for air for two? Does the second trip allow you to extend your days on your own dime if you want to see more of Italy? Is the 6 day trip to Milan just right for you or do you really want to see Rome?

Another example: you really want to see Machu Picchu. But are you interested in the 8-day all-expense paid trip there with the yoga excursion that focuses on specific chakras? Or you want to go to Scotland but do you want the 10-day trip that sees the Scottish Highlands by way of hikes and whisky testing? I’m all for the shotgun approach to entering every trip but make sure you know what the prize is and what to expect.

There tend to be two types of travel contests. Most are based on pure luck and some are what I loosely call skill contests. Luck is as simple as entering your name. Luck helped us “win” the drawing for the Final Four tickets in New Orleans. Because of this we could buy directly from the NCAA without getting gouged. Same with the Master’s practice round tickets. Luck helped my husband win a trip to Cancun at a bar’s trivia night. All you had to do was show up! These are the easiest to enter and thus most people flock to win these travel contests.

Skill contests call out to all of us 80s/90s kids that loved Where in the World is Carmen San Diego? They tend to be trivia type contests that involve some geographic knowledge (or the ability to operate a search engine.)

That’s how I won the trip Down Under, guessing each of the locations in Australia from the hints and pinning a map. It’s also how I got that t-shirt from Expedia as one of the 25 runner-ups. (Grand prize got 1 million Expedia points) But hey, that’s ok, I won that t-shirt 7 years ago and still sleep in it. So it’s pretty much the same as a free trip to Paris! Right? Sigh. Regardless, these contests are a bit harder or take a bit more time so the odds are more in your favor.

Maximizing Your Travel Contest Time- Better Odds, Cleaner Inbox

Last piece, addressing how to enter these without it taking over your life. First, I strongly recommend that you set up an additional email that you use when you enter trips. I am not saying make a whole bunch of extra email addresses and enter them all! As I mentioned, if you win, you have to prove who you are. If you tried to hustle the system, they will disqualify you sooner or later. What I am saying is consider making an extra email address that you use solely for entering contests and only enter contests from that one address.

A designated contest email funnels all of the extra things that you will get signed up for into this space and you can keep this separate from your regular life. You scan for the “you won” titles and delete or read the rest at your leisure. Not only does it keep your main inbox cleaner, it makes you less likely to accidently delete an important email. I almost deleted that winning email for Australia. This close.  They wouldn’t have sent it twice and I had 72 hours to respond before they moved on. (Note: 72 hours to respond is standard. Then you’re out.)  I was about ready to junk it when I was on a cleaning spree in my regular inbox. I’ve kept things separate since.

Once you enter travel contests, you will find that similar sites that offer contests will now be in your inbox. They build upon themselves, thus more contest emails. You will start to get an idea for the companies that give out really fantastic trips and the ones that are able to sponsor portions of some great destinations. I’ll also post some of the best sites on my page as well.

Finally, most contests are a one time only submission. Enter and wait. A few, however, allow daily or weekly entries. I star those ones and return to them regularly to re-enter. I’m not a math wiz but even I know 30 entries give me better odds than 1. You must decide if it’s worth it to you. Additionally, many sites will offer extra entries if you share the contest on social media. I ‘m still learning social media, but I do post on Facebook and follow on Instagram to help my friends and get my entries. Just remember people may get sick of the spam.

So keep your eyes open for legitimate trips that fit your interests and jump right in. You may win nothing. You may get some t-shirts on your doorstep after playing a fun, online scavenger hunt. Or you may find yourself in seat 26B, between your spouse and the ecstatic, ultimately Bali wedding-bound Robert, getting ready to leave LAX and fly 13 hours to the other side of the planet. It’s a great big world out there, and almost anything can happen. Enter those travel contests and prepare to win! If you’re not prepared to wait for the win, there are always ways to hussle flight points, hussle hotel points, and other travel hacks to make those dream trips come true.

May the road rise to meet you, travelers, and may Lady Luck be by your side.

If you don’t win a trip, you can still go. Don’t call it a dream, call it a plan. Grab a Dragontree Rituals of Living Dreambook Planner. It’s been making my goals happen for 5 years.