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How I went to Hawaii for Free

By David Carlson / Last updated: November 7, 2015 / Giveaway, Lifestyle, Save Money, Travel

We may receive compensation from companies mentioned within this post via affiliate links. Read our full advertiser disclosure. Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities.
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How I went to Hawaii for Free
This is a sponsored post. I am a Shop Your Way blogger, but all opinions are my own.

Every single day there are hundreds – no, thousands – of articles published about travel.

One topic related to travel that people like to read and write about is travel hacking. Travel hacking is using credit card rewards and other strategies to travel for cheap or even free.

Every once in a while we’ll have articles about travel hacking. For example I wrote this post explaining How to go to Vegas for Free. I also warned people not to throw out their junk mail in Mail Credit Card Offers > Online Credit Card Offers.

Those of you who are familiar with travel hacking know that it’s entirely possible to get free or reduced trips if you plan properly.

You also likely assume that I used credit card rewards to go to Hawaii for free.

That was not the case.

So how did I go to Hawaii for free? Allow me to explain.

How I went to Hawaii for Free

You’ve probably watched someone win a trip on Wheel of Fortune or The Price is Right, but it almost seems fake because, seriously, how many people actually win trips?

I used to feel that way. Until I became one of those people. I won a free trip to Hawaii

Now, I didn’t go on a game show to win. I didn’t even have to leave my home. I did it through an online giveaway.

What I won was as week-long trip to Hawaii for two including airfare and hotel. The value was close to $5,000 and we stayed at the Royal Hawaiian on Waikiki beach.

It still seems surreal to know that I won the trip, but knowing what I know now it is far from an impossibility.

The Hawaii trip actually is the second trip I won. The other trip I won was a trip to the MLB All-Star Game.

The ironic thing was that the All-Star game was in Minneapolis that year so it was already in my home town. Instead of getting free flights I negotiated getting $500 cash. My wife and I did stay in a (nice) hotel for free, just for fun. We ended up selling the $300 face value All-Star game tickets on Stub Hub and pocketed the cash.

One thing people don’t realize is just how many online giveaways and sweepstakes are out there. I don’t think it’s an understatement to say that thousands of online giveaways end every single week.

The difficulty with giveaways is that you have to know where to look for them. Some are in obscure places. For example the band Incubus gave away a trip to Las Vegas recently but you wouldn’t really know about it unless you were on their email list.

My wife and I used to put together a weekly “giveaway roundup” post on Young Adult Money that went up every Friday. It had between 100-300 giveaways that were ending within the next week. It was a pretty popular post but took a lot of time and effort to put together. Unfortunately we had to discontinue it once my wife started grad school.

Where do you find these giveaways?

One valuable thing about Shop Your Way is that they typically have hundreds of giveaways going on at any one time, including travel giveaways. Right now they are giving away a trip to Las Vegas that includes tickets and backstage passes to Maroon 5’s New Year’s Eve show. The trip has an approximate retail value of $2,895.

I don’t know about you, but regardless of what “extras” are included in the trip, but I’m always up for a free trip to Vegas!

Like I said, there are typically hundreds of giveaways going on at Shop Your Way. You can view them by category, such as “Getaways,” or view them all at once.

SYW Giveaways

As someone who has entered thousands of giveaways over the past few years (and won some big ones), believe me when I say there is huge value in being able to enter a bunch of giveaways all in one place. Most people who enter multiple giveaways end up jumping from site to site. With Shop Your Way you can enter a ton without having to jump around to different sites for different giveaways.

While there are tons of other giveaways, there is one particular one that I wanted to highlight today. It runs through November 17th, so you’ll have to head over there ASAP if you want to enter this one.

The giveaway is called WANT IT. WIN IT. NOW!. What you do is you create a wish list on ShopYourWay.com, enter the giveaway, and find out instantly if you’ve won what you want. It’s that simple!

If you want to enter the WANT IT. WIN IT. NOW! giveaway head on over to ShopYourWay.com/WinNow. Past the giveaway date? No worries – like I said, there are tons of giveaways on the site!

To get you excited about winning some awesome free stuff, here’s a few pics from our free trip to Hawaii:

Hanauma Bay

Royal Hawaiian

The Royal Hawaiian 2

Waikiki Beach

P1110688

P1110579

P1110524

P1110776

Who knows? Maybe you’ll win a giveaway to go to Hawaii for free!

Check out all the giveaways at ShopYourWay.com.

What giveaways have you won? Do you like the idea of being able to enter multiple giveaways all at one website?

All photos copyright David Carlson.

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David Carlson

David Carlson is the founder of Young Adult Money. He is a nationally recognized speaker and the author of Student Loan Solution (2019) and Hustle Away Debt (2016). His opinions have been featured on such media outlets as The New York Times, The Washington Post, Cheddar, NBC's KARE11, and more.
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Comments, responses, and other user-generated content is not provided or commissioned by this site or our advertisers. Responses have not been reviewed, approved, or otherwise endorsed by this website or its advertisers. It is not the responsibility of advertisers or this website to ensure that all comments and/or questions are answered. With all that being said, please comment away!

Reader Interactions

Comments

  1. theYachtless says

    Wow, that is so amazing that you got to take that trip! Coincidentally, I was actually in Hawaii a couple of months ago, and I totally know that hotel, even though I did not stay in it. I was only in Waikiki for about a day and then drove around Oahu and camped (a nice cheap way to see the island!). It was an amazing trip, especially since I hadn’t taken a vacation in years. It sounds like you had a fantastic trip too! I will definitely check out Shop Your Way, as I am always up for free travel. :)

  2. DC @ Young Adult Money says

    theYachtless That’s awesome that you were in Hawaii!  I bet camping was a good way to save money as hotels seem to be the reason going to Hawaii ends up being so dang expensive.  Oahu is a beautiful island and we were lucky enough to be able to make a loop around it one of the days and see the North Shore.  The eastern side of the island is incredible.

  3. mycareercrusade says

    Great pics DC, not sure if I’ve seen them on Facebook previously but they’re awesome buddy!
    Love the idea of being able to enter multiple give-aways at one site, you considering a new business idea?
    Cheers & hope you’re well :)

  4. Gary @ Super Saving Tips says

    Great pix! My wife enters a lot of giveaways and won a $1,000 Amazon gift card earlier this year. I don’t think she enters on Shop Your Way though, so I’ll have to mention it to her.

  5. DC @ Young Adult Money says

    mycareercrusade Thanks man, it was a wonderful trip!  Almost forgot to tell you we were *almost* going to go to Australia this Summer (our Summer), but it would be too cold.  My wife wants to scuba dive in the great barrier reef!  I told her you lived there, though, and it would be awesome to meet up sometime down the road.

  6. DC @ Young Adult Money says

    Gary @ Super Saving Tips Wow that’s a big win!  Congrats to her!

  7. Jason @ The Butler Journal says

    Looks like you had a wonderful time in Hawaii. I still haven’t won any major giveaways yet, but I know my time is coming.

  8. twocuphouse says

    Thanks for sharing!  I hadn’t heard of this before, but we’ll be checking it out this weekend.  Wouldn’t mind a vacay, myself.  ;)

  9. DC @ Young Adult Money says

    Jason @ The Butler Journal You’re due, Jason!  Best of luck!

  10. DC @ Young Adult Money says

    twocuphouse No problem! Best of luck winning a giveaway1

  11. howtoliveinus says

    Incredible! I recently went to Hawaii myself and reduced my costs by a lot, but this is just over the top! Hope you had a great time!

    PEter

  12. DC @ Young Adult Money says

    howtoliveinus Thanks, we definitely had an amazing time.  I hope you had a good time in Hawaii as well!

  13. Chonce says

    That’s awesome that you won the trip! It looks like you had a ton of fun. I tend to have decent luck with raffles and I don’t really have anything to lose so I will definitely look into this.

  14. DC @ Young Adult Money says

    Chonce Best of luck, Chonce!  I would love to win another big trip like this, so I keep on entering the big giveaways.  It’s really crazy to go somewhere like Hawaii for free!

  15. believeinabudget says

    Awesome!! That’s quite a vacation to win. I tend to do fairly well with raffles. I think the biggest item thing I have won were a couple annual tickets to Universal Studios (which was great when I lived in Orlando.) I don’t know if anything can top Hawaii though!

  16. Laura Beth @ How To Get Rich Slowly says

    I have never won anything in my life. But I’m heading over there now to check it out!

  17. DC @ Young Adult Money says

    believeinabudget Considering how expensive amusement parks have become, those Universal Studios annual passes seem like a HUGE win! Congrats!

    I saw a giveaway for a trip to the Maldives a year ago.  I think that’s the one travel giveaway that would top Hawaii.

  18. DC @ Young Adult Money says

    Laura Beth @ How To Get Rich Slowly Good luck!  You can’t win if you don’t enter ;)

  19. Eyesonthedollar says

    That is the best prize I’ve seen anyone win online. I have won a few giveaways, but nothing like a trip to Hawaii. I’m glad you guys got to go and enjoy.

  20. DC @ Young Adult Money says

    Eyesonthedollar Thanks Kim!  It still feels surreal.  It was such an incredible vacation.

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