How To Win A Free Trip Abroad

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Me winning a free trip abroad

Of course, this goes without saying but I’ll say it anyway. The first thing you need to do to win a free trip abroad is to simply show up? Now you probably wondering, “Show up where?” In my case, I joined a community called Travel Massive in October of 2016 after attending an event they hosted at the TBEX conference in Manila. Being a traveler, it was only logical to remain active with the Chicago Travel Massive chapter once I returned home. A question you can ask yourself; however, is:

What can I gain from joining a group like travel massive or something similar?

All smile from the winning 4

Local events with like-minded travelers

Most of the Travel Massive events I’ve attended have been pretty darn awesome. Drinks, food, sometimes dancing, but always great conversation and connections made.

  1. The first event I attended upon returning home was hosted by Toronto tourism. Although I didn’t win anything, my attendance at least gave me a chance. And attending alone was a blast! It was held at Goose Island Brewery and featured an open bar, great food, a tour of the brewery, and a networking session with other travelers and travel professionals.
  2. My second event was hosted by Fort Myers and Sanibel tourism. While the food wasn’t as good as the spread put on by Toronto tourism (sorry Fort Myersjust keeping it real!), I did win one of the prizes of the evening. Not a trip, but a pretty sweet backpack—baby stepping toward the BIG prize.
free backpack

Thanks Fort Myers and Sanibel Tourism!

  1. I’ve heard the phrase, “third time’s the charm” and I must admit—it just might be true. I am EG III, after all, named after my father and grandfather, but the third and most modern version. And at my third and most recent Travel Massive event (which took place during the third week of November–coincidence I think not), out of hundreds of attendees, yours truly won the golden goose. Roundtrip airfare and a 5-day, 4-night stay at a boutique hotel in Taipei, Taiwan!

Arrival at the airport in Taiwan

Well, I sort of won…

How it all went down

A big reason why going to the events and networking is important are the people you meet and the friendships/relationships you build. While attending the Fort Myers event, I had the opportunity to speak with several people throughout the course of the night. One person from that evening, Arnold, crossed my path once again at the Taiwan-hosted event. While I won’t go into all the conversation details, the most important exchange went kind of like this:

Where’s your plus-one that will accompany you if you win?” I asked.

“I didn’t bring one. What about you?” he replied.

Couldn’t make it. My sister was supposed to join me and she canceled last minute.” I followed.

“Well, how about this? If I win, you’re my plus one and if you win, I’ll be yours.” Arnold continued.

That’s a bet. Deal!

Imagine my surprise when the first name chosen was Arnold! And the rest, as they say, is history…

Even though my name wasn’t called, thanks to a bit of luck and perhaps divine intervention, I still managed to walk away a winner!

Me winning a free trip abroad

Other places to look for scoring a free trip abroad

Travel Massive is not the end all be all when it comes to winning a free trip abroad. If you live near a major city, then be on the lookout for tourism boards that periodically come into town to promote their destination. Another option is by simply entering competitions online. Begin your search at websites like the balance, which have comprehensive listings for numerous trips and competitions you can enter for free!

Best of luck my travel friends, and remember if you’re in need of a plus oneI’m your guy!

Elephant Trail hike

The view of Taipei from Elephant Trail hike

Taipei City tour

Paparazzi was out and I was all smiles!

In the comments below, let me know what the best thing you’ve ever won has been!


  1. Yes, one must show up. This means a lot of hard work, a friendly nature and help from God. By the way, I clicked the link of the balance website. I thought I would let you know that.

  2. Milton Coyne says:

    oh my gosh I wanna experience this too!!! I never had a chance to travel abroad but I do love traveling in different places in the country.. one thing great about living in an archipelago is that each island offers dfferent taste and experience hehe
    Anyway, since you have mentioned that TBEX in Manila… I suppose they have chapter here in my country too (Philippines)
    Gosh I would like to meet other travel buddies through ths group too

    • EG III says:

      I met a TON of bloggers from the Philippines at TBEX Manila. You should definitely link up with some because your country rocks when it comes to social media activity and engagement!

  3. Natasha says:

    What a great turn of events! Nice way to end your third travel massive. And what a heartwarming story. I’m sure your friendship with Arnold was solidified then too!

  4. Wow, congrats man, and kudos to Arnold for keeping his word! I’ll definitely be checking out Travel Massive after reading this. Even if i don’t win a trip, the connections and experiences seem amazing

  5. Stacie says:

    A free trip? I’m down for that. I’ve always thought things like this were too good to be true but I guess not!

  6. Kim says:

    Sooo I never heard of Travel Massive, and now I have to research, especially if it means a free trip. I have always been skeptical about entering contests for trips because I never thought they actually chose a winner.

    • EG III says:

      I was a skeptic too…but now I’m living proof!! It kind of reminds me of a time I went to see a pair of illusionist perform. I was a skeptic then until they took me up on stage and I became a part of the performance.

  7. I always consider myself lucky. I win things, but never anything as cool as a trip to someplace over seas. Congratulations! This is such a fantastic experience.

  8. I need to win a free trip! I got the travel itch back in July was able to travel again in September and now I’m itchy again. HAVE FUN!!!

  9. This is awesome! Who doesn’t love a good free trip!

  10. Krupa says:

    Congratulations! Winning a trip to abroad is great. You are so lucky. I never tried showing up for any kind of conferences n stuff so I think I need to do that. Thanks for sharing .

  11. Ashley DTKAustin says:

    SO AWESOME!!!!! I am seriously so jealous!! I never win anything so enjoy!!!!

  12. KatWalkSF says:

    So many great ideas!

  13. Regina says:

    Great article! I’m realizing I need to travel and get out more! Great post!

  14. This sounds like a fabulous idea! I need to win a free tip to ring in the new year!

  15. Dominique says:

    I’m a major lover of travel. Going to put your tips to good use!

  16. Danijela says:

    Hehehe, so lovely! Hope you and Arnold had some great time in Taipei. I’m sure you’ll write about that one, right?
    Incredible how everything regarding travel can be unpredictable, even at such an event! 🙂

  17. Dope! I gotta get out more and see this world. Loved this post.

  18. Britney says:

    Congrats! This is awesome! Thanks for sharing! Until now, I had never heard of Travel Massive or anything similar.

  19. Chelsea says:

    I’ve never heard of this group. I definitely need a vacation so I may have to consider it.

  20. Joyce Brewer says:

    Congratulations. I had a streak where I would win lots of prizes at events. I once won a small smoker/bbq grill, but I left it at my old house when I moved.

  21. Eva says:

    This is really cool! I gotta get my son to do more traveling. He is 18, has a passport, and I don’t think he understands the powerful combination of a US passport and youth!

  22. Mimi Green says:

    That’s so freaking dope. Sometimes timing is everything, you were at the right place at the right time. Congrats! I can’t think of anything I’ve won that was amazing. I need to enter more contest.

  23. Kita says:

    I need to be a part of this travel massive. I’ve never traveled abroad but looking forward to it nest year.

  24. Rachel says:

    thanks for the heads up about Travel Massive, I just had a look and joined up – but looks a little quieter over here in the UK. The balance looks really cool – do you know if its only open to US residents though, non e of them seem to be available for anywhere else 🙁

    • EG III says:

      While a large majority of their contest do tailor toward US/Canadian residents, they have some international ones as well.

  25. Kasi says:

    These are great tips and orgs to join for travel lovers. Congrats on sort of winning the free trip, lol! Looks like you had a great time!

  26. Tomiko says:

    I receive their emails but never read them.. I literally deleted an email from them yesterday.. heads to deleted files to go retrieve the email now

  27. I love Travel Massive. I am a part of their Philadelphia chapter! I have to check out their events though!

  28. I am definitely down for winning a free trip abroad haha! I just checked out Travel Massive for myself and it sounds like a wonderful community to be part of! I just joined .

  29. Ola says:

    I’ve never heard of Travel Massive before. But I must say it’s exciting to hear that there is a chapter in my hometown Chicago. I’d like to go to at least one even to see what it’s about. So I’ll check them out next. Thanks!

  30. Travis Is Everything says:

    My man international!… Whenever you get back in Chicagoland Area, we gotta get up at L.A. Fitness so I can run you out the GYM!!!

  31. Nikoleta says:

    I want one of those! 🙂

  32. Patty says:

    This sounds amazing and totally worth it!

  33. Amalia says:

    You’re so lucky!! Looks like Travel Massive is a great community to join to, enjoy your travels!

  34. Chris Buggs says:

    That adventure looks and sounds magical!

  35. Tisha says:

    Congrats! There’s nothing I need more rn than a free trip! Will have to start looking for similar offers in my area!

  36. How fun! That is so awesome that you won!

  37. Julia Comil says:

    I did not know about this!! Great article!!

  38. Polly Doyke says:

    You are the coolest guy who is a master at connecting and letting the forces work for you. You are my inspiration! I have never won anything yet but I am certain I will.

  39. Never heard of this but it looks like a great idea. I definitely want to do more traveling next year.

  40. WHOA!!! What the??? I never heard of this before. I need to get hip and connected! That’s what’s up!

  41. Michael-Paul Dix says:

    Damn! I need to get up on that! There’s a big world to see. Congratulations

  42. Tamara K. Young-King says:

    Eddie, great article! Congratulations doesn’t seem adequate. Can you say LUCKY BASTARD! Really, my absence secured your victory, if i had been there Arnold would have to have gone without you. Regardless, I’m so excited for you as begin your domestic journey to continue your international life . I know Mommy is beaming because you are living her dream of seeing the world! LOVE YOU BROTHER!

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