How I Win Free Trips With My Sweepstaking Habit

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How I Win Free Trips With My Sweepstaking Habit

I Win Free Trips With My Sweepstaking Habit

I won a trip to Holguin, Cuba, where I smoked cigars, basked in tropical rainstorms, and listened to the locals tell stories that taught me a hell of a lot more about Cuba than I thought I knew.

I won a trip to Whistler, British Columbia that included whitewater rafting, ziplining, mountain biking, and a many-course dinner for two (guys, there was a cocktail that tasted more like cake than cake does).

At the beginning of this year, I won $1,000 in tickets for music festivals on beautiful Vancouver Island that provided me with a whole slew of sunny days full of cider to look forward to.

My two free trips to New York City were especially thrilling – one included car service and a Broadway show! I used to live there and I can tell you that no, I was certainly not residing in midtown, and yes, I was certainly surviving off of corn meal cakes dipped in ketchup, or 99c fresh slice if I was feeling lavish.

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The author on her winning trip to Cuba, exhibiting a standard basic bitch pose sure to do her ancestors proud

Okay, okay. How did I get so “lucky”?

I guess Benjamin Franklin said it best when he said, “diligence is the mother of good luck”. He also said that wine is “constant proof that God loves us, and loves to see us happy”, so I’m not going to argue with the guy.

Look. Maybe you get up early to watch the sunrise, or maybe you even get up early to go for a run (wow, that’s cute no really, wow, good for you). Well, I get up early and sweepstake.

How To Win Free Trips By Sweepstaking

My treasured morning routine, which often ends up being a highlight of my day, is waking up, turning classical radio on (don’t mess with my Dvorak), making coffee, and opening about 150 Google Chrome tabs simultaneously. It’s sort of reminiscent of extreme couponing, but while you do sometimes end up with a year’s supply of toilet paper, you also have a shot at going on an all-expenses-paid trip.

The idea is simple: Find contests, and enter them.

There’s no big secret to it, other than sourcing the contests (I’m not going to spell it out for you, but Google is your friend). I’ve inspired a few people to start… and they lasted a few days before getting incredibly bored, which leaves organizational freaks like me to win the BBQ’s and the electric toothbrushes… or most recently, $25 to a local sex shop (I’ll take the FANCY lube please)!

But if you’re truly interested in winning free trips by sweepstaking:

  1. Find contests, and figure out which ones are worth entering for you.
  2. If they allow daily entry, keep track of them so you can revisit them each day. You could do this in your bookmarks, or perhaps a delightful spreadsheet. Ooh!
  3. Delete a contest when it ends, and add to the list when you find a new one.
  4. Check your email regularly. This includes all spam folders.
  5. Rinse, repeat.
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The author on her winning trip to Whistler, smiling through her certainty of impending death.

You learn things along the way, like creating a separate email, so you don’t end up drowning in spam. Each contest must by law have their “rules & regulations” available – become acquainted with them, and follow them explicitly. They will tell you how much of your information is, essentially, being shared/sold (you’ll have to decide what you’re comfortable with, if you are comfortable with it at all) and will also tell you what the contest provider considers “one day”, in relation to how often you can enter. It could be 24 hours from your last entry, or perhaps they reset their entries at midnight EST.

Here is also where you will discover if you are not eligible for the prize – this happens often for Quebecers due to various Canadian law, and could also be the case if you’ve already won a prize from the mother company in a certain period of time. It’s all tedious… and I revel in it.

If organizational tasks were a chocolate fountain, I would STICK MY FACE IN IT.

Then again, if a chocolate fountain was a chocolate fountain, I would also stick my face in it. I digress. What I’m saying is that I’m the kind of person that will organize your filing cabinet for you, and like it. I mean, I am a self-employed contract worker, and I still do my own taxes. You get it.

How did this slightly-embarrassing and highly-satisfying sweepstaking hobby start?

Well, my friend won a trip to Vegas from MTV, and I prodded her about it until she explained the concept of “contesting” to me. She’s since given it up because I guess she has a life, or something, but I carry on her legacy. I started in 2012, and in a streak of beginner’s luck, won $1,000 at HMV. That was all it took to hook me, and here I am five years later, a few vacations and a couple Nintendo DS’s richer.

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The author on her winning trip to New York City, thinking hard about pizza

But Is Winning Free Trips From Sweepstaking For You?

Keep in mind, it’s not all sunshine and Kitchen Aid mixers. While I only spend about half an hour per day doing it, which seems to surprise people more than anything else, it took time to organize my system in the first place. Oh, and did I mention that you should check your spam folders? I’ll say it again: check them. Or don’t, and end up like me, losing a $13,000 cash prize from Listerine because you didn’t realize you had an additional junk mail folder in your brand new gmail account, hiding in a drop down menu. Oh, the Antarctica trip that could have been.

Anyway, you can easily go months or more with nothing but a 25% off yogurt coupon to show for your time, so if you’re impatient, it may not be the hobby for you. Make peace with the fact that you may never win that coveted vacation. I do it for the process, the routine, and the rush of birthday-like joy when I get that special phone call or email. If you’re American, note that you may have to pay taxes on your wins, whereas Canadians such as myself, do not. #canadianprivilege #notallcanadians #waityesallcanadians

Sweeptstaking is a weird hobby, and I’m a weird lady, and that shit just works out.

Maybe it will work out for you, too. However, travel is a privilege I cherish. I’d be remiss if I wrote a post for a travel website, let alone a particularly woke travel website (raise your damn hands for Kiona), without noting that being born into a nation with a strong passport is major, and that being Caucasian affords me a certain freedom to travel without the comparable stigma and challenges that a Woman Of Color may experience in so many countries. I keep these facts in mind when I use my hard-earned pennies from my 60+ hour work weeks to travel the world, and if I can occasionally travel on someone else’s dime, you bet I will.

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The author in her natural habitat, on a trip she paid for her own damn self.
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About The Author

You can find Giordana working as a stand-in on a film set in British Columbia or hiking up mountains with her dog, David Bowie. Follow her woodsy adventures on the social media buttons below! Disclaimer: She is not a travel blogger. She doesn’t even own a floppy hat. 

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