Are you stressed out at work and ready for a vacation? Or perhaps the winter blues have you wishing you could head South? It is time to get away! How amazing would it be if that escape of yours was free because you won the trip? Sounds to good to be true, right? But it’s not. On any given day there are over a hundred legit travel sweepstakes you could be entering to win a vacation.
Last fall I had just gotten home from an amazing vacation in Thailand (I paid for that one out of pocket, unfortunately!). I realized I had no other planned vacation in my future and of course my travel budget was running low having just gotten home from a trip. Winter was coming though, and I really wanted a tropical escape- some sun and sand is so rejuvenating part way through the long winter. Filled with hope, I found a listing of travel sweepstakes, and went down the list entering them. In December, the phone call came, I had won a cruise from Florida to Mexico! The prize also included our flights and all ground transportation. A couple months later my husband and I were snorkeling in Cozumel and I couldn’t stop thinking “Wow, I won this!”.
To help beginners and advanced sweepers alike, here are some of my favorite tips for winning travel prizes. Hopefully this winter it will be you on that beach.
8 Tips to Find & Win More Travel Sweepstakes
1) Find a reliable list of sweepstakes.
Actually, find a few reliable lists of sweepstakes. You can find your state’s listing and search for travel sweepstakes for your state or region. There are also large national listings that you can filter by prize. My favorite lists, for sorting by prize, are from The Balance. They offer a list of travel within the United States and a separate list for international travel. This can be nice if you don’t have a passport, you could just enter from the United State’s list. You will also want to filter listings to show which ones are expiring first, that way you won’t miss an entry before the sweepstake closes.
2) Enter daily sweepstakes daily.
Once you have had entering sweepstakes as a hobby for a while, you quickly learn the importance of this once. It is really just basic math. If the sweepstake has a 30 day entry period and you are allowed one entry per day, a person who enters 30 times is much more likely to win than the person who only has one entry in the running. Finding daily entries could increase your odds because most people aren’t going to remember or have the commitment to enter every single day, so you will hopefully have more entries when it closes. This does not have to take a lot of time. With a program like Roboform or using your phone’s autocomplete mode, you can fill in the entry form very quickly each day. Learn more about efficiently entering sweepstakes here.
3) Really focus on finding local ones.
This is all about increasing your odds again. If the sweepstake is only open to people residing in your state, think of how many less people are going to enter that than a large national contest. You can also be on the lookout for ones you need to enter in person. I’ve seen new banks and grocery stores both offer vacation giveaways when you came, in person, to visit their new location. Plus, I always get a thrill out of folding my paper entry form trying to put lots of folds in it, so they have so many spots to grab my lucky little slip (We should have seen this hobby coming when I was a child, because I’ve been doing that for as long as I can remember!).
4) Look for niche/demographic specific sweepstakes.
This once again, you guessed it, increases your odds. If you have a passport, enter all the international ones. Less people are entering those if they are focusing on US only trips. There are also hobby specific trips like dive trips, ski trips and rugged trips out West. I saw one recently for a ski trip. If it had just been for me to go stay at a ski resort in Alaska, I would have entered in a heart beat, but this trip included going out every day on off beaten paths and being taken there by helicopter. Now I ski, but it is much closer to bunny hill sking than being dropped out of a helicopter. There is no way I would have been able to keep up if I had won this trip, and I feel it would be a little rude to take a prize like that from someone who would be fulfilling a life dream by winning it. The point is, only very serious skiers could enter to win that one, and it really trims down the amount of eligible people to enter – less enteries, better odds for you.
5) Google “enter to win” and “all inclusive” or “Bahamas”.
Knowing key words to search such as “enter to win” or “official rules” and then searching a place or a phrase like “all inclusive” can help turn up results of sweepstakes not listed on popular listing websites. Make sure to set your Google search to results from the past week or month, so that you are only seeing current results.
6) Follow travel companies on social media.
Travel websites and resorts sometimes have giveaways that are only available on their social media channels and better yet, some of them have short entry periods. Make sure you are following the official page of these companies. There are quiet a few spam ones out there that claim to be giving away dream vacations, but they aren’t the official social media page of that company. Alaska Air wrote a nice blog post about this very topic. If you want to learn more about how to tell if a social media contest is legit, check out their post.
7) Expand to skill based contests.
Even if you don’t think you are the best writer or photographer, I highly encourage you to still check out some skill based contest. Instead of just throwing your name in a hat for these companies will judge your entry for a writing, photo, video or recipe contest. The key to these are to read the official rules and see what the judging criteria is and what rules are all in place. A photo contest might not allow logos to be shown in the picture and require the photograph to be a certain size. Think how many people enter these without reading the rules and get themselves disqualified. Simply following the rules will narrow it down to less entries. Really cater your entry to fit exactly what the sponsor is looking for in their judging criteria. Contest entries take much longer than hitting auto-fill, so many people won’t take the time or effort to enter. That helps make these contests more winnable. I’ve been fortunate enough to win a pair of airplane tickets from one writing contest and some cash that we used for a vacation on another- so needless to say I am hooked!
8) Share ones with referrals to get max entries.
Giveaways that are run through Gleam or Woobox and a couple other platforms usually have the option to share to receive more entries. Some of these are very lucrative and will offer you five more entries for each person you get to sign up, so it is definitely worth taking advantage of this. I prefer to post these shared posts on sweepstake specific Facebook groups that are set to ‘Closed’ or ‘Secret’, so that I am not constantly posting on my own Facebook page and possibly annoying friends and family that don’t care to enter.