I was walking to my train to work one morning listening to the She Explores Podcast. I like to listen to stories of adventures and the outdoors on my commute downtown because it gives me a little mental escape from my office in the city before I start my day. 

This episode was about how the guest speaker became a Park Ranger in New Zealand, so it was perfect to start my day before heading to my mundane job downtown. To my surprise, she had gotten the opportunity starting by entering and winning a contest for a free flight to New Zealand.

Then, being the savvy child of two park rangers, she worked it out to spend the longest time she could on her visa there. She traveled to New Zealand for six months gaining experience working for the parks and making the necessary connections for a more long-term position.

My main takeaway was that this girl changed her life to one of adventure in New Zealand from a contest! I see these giveaways and contests all the time, on the radio, on social media, at public events – and always wonder if anyone actually wins those things. Now I never pass up the opportunity, and I have won quite a few little things over the years. By far, though, the best contest I won was the time we went on our honeymoon for nearly free. Keep reading to see how we did it.

Our Original Honeymoon Plans Were Canceled

My husband (who is Costa Rican) and I got married in Costa Rica. We planned to honeymoon in Cancun, Mexico as it is a bit more budget friendly than Costa Rica. While we were planning the festivities, I got into the habit of entering giveaways and contests in the hopes of having a fun luxurious honeymoon, stretching our tight budget a bit further for the whole celebration. Unfortunately, nothing panned out, but I subscribed to so many things that my inbox was completely out of control (oops!) 

We ended up purchasing a budget flight to Cancun from Costa Rica. The plan was to stay in an all-inclusive resort, figuring that it would save us from spending too much going out and about the whole week. Later, though, due to unforeseen circumstances we needed to cancel those plans. We postponed the honeymoon while we moved entirely across the country to Seattle, and got settled in.

Chateau Ste Michelle

A Local Winery Hosted a Giveaway Contest

That Christmas, I noticed a local winery in Washington announced a photo contest for the holidays. Each week, you could submit a photo that matched the theme, which the winery used to choose a winner. 

Then, each winner also entered into the final round for the grand prize. I entered every single week, with pictures of holiday crafts, light decorations, date night, celebrations, etc. Finally, during the last week, the contest was for a photo of a holiday party.

We entered a photo from a 20’s themed party and I couldn’t believe it but the winery chose our photo! We won that week! The prizes included an event-hosting book, a winery-themed blanket, a marble and wood cutting board, plastic stemless wine glasses (which happen to now be my favorite ones to use), some cheese labels, and a marble wine stopper.

We Were Entered for the Grand Prize

The only time I ever remember winning something before was back when Teen Magazine used to put a code every day on the calendar and if you went online to enter it, you were entered for that day’s giveaway. I received a package with some scented chapsticks that I had completely forgotten about entering the contest for, and I was just ecstatic. Then this winery contest was so much more exciting to win!

After the holidays the winery put the 5 winners of each week’s contest together into an album on social media. This time the Grand Prize Winner would have their photo’s likes counted as votes towards their overall score, along with other criteria the winery would use. 

My friends and family shared the post all over social media and everyone pitched in to help us win. We far surpassed the rest of the entrants, but the votes were only a part of the score so we still weren’t sure if we would be the grand prize winners. Finally, after an agonizing wait of approximately one day (haha) we found out we won and couldn’t believe it!

The Reward

We were beyond ourselves with excitement and thankful to everyone who helped us get the votes that helped us win. 

The grand prize was amazing, and included a full set of red, white, and champagne wine glasses, a tablet, a luggage from Nordstrom’s and some packing cubes, a $100 spa gift card, a GoPro, a $1,000 gift card to Airbnb, and a $1,000 Visa gift card. 

With all of this we would finally be able to take our honeymoon, so we began to plan it out.

Unfortunately, when we originally canceled our trip, the travel agent had booked the all-inclusive resort stay through some third-party organization. They refused to refund us or extend credit despite our extenuating circumstances. We would have to start over on accommodations from scratch. The budget airline also had a policy against cancellation. However, after a long emotional phone call with customer service they agreed to let us use the flight credit.

When we originally bought our flights we were planning to fly round-trip from Costa Rica. Now that we were in Seattle, the flights with this airline to Cancun were going to cost double the price. Our airline credit covered one seat and the $1,000 Visa gift card we had won covered the rest.

We love the idea of supporting locals when we travel. We were also a little sour after being stung by the resort not helping us move our stay or refund. This meant we were not inclined to stay in another resort. Winning this contest with an Airbnb gift card allowed us to pivot from the all-inclusive stay we had previously planned, and instead search for locally-owned accommodation.

We Used the Prize to Travel to Mexico

That summer we finally got to take our honeymoon. I completely fell in love with Mexico during our week there. We decided to spend half our time in Playa del Carmen. On the last day, we rented a car to pack up our things and spend the day exploring Chichen Itza. Using the remainder of the Visa gift card we rented the car and drove to Chichen Itza, since it’s located between our two stays.

After that we returned to the Cancun area for our last few nights. We found two Airbnbs, one in each town, each with a pool and close to the ocean. They were close to everything we needed, but not quite in the touristy “Zona Hotelera”.

The key things to look for to make sure you are supporting someone local and not international are location, reviews, and the owner’s profile. If they have a ton of listings under their name, they are likely investing in rental properties. To support locals we avoided any listings like that. Our stay in Playa del Carmen was owned by someone who turned out to live in Canada, but it was his only property listed on the app.

The stay in Cancun was just outside of the “hotel zone” and owned and operated as an Airbnb by two local Mexican women. They were so friendly and hospitable, and it was an absolutely lovely stay. They were even able to recommend an authentic restaurant around the block for some of the most delicious Mexican food.

Moving Forward

Ever since that trip, I have been entering different travel and giveaway contests on social media and through email. I am hoping for another huge win but it has not happened since. I have won a few smaller contests in the meantime. 

A printed photo of Seattle from a local photographer, a healthy care package that included some of those Bolthouse smoothies and juices and a workout clothing set through Instagram giveaways to name a few. Even so, there hasn’t been anything as big as this winery giveaway that funded our honeymoon. Now that I know it is possible though, I will keep trying! 

What about you, are you convinced to start entering giveaways and contests now? Have you ever won a travel giveaway? Let me know in the comments!

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