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Travel Tales & Fails
 Submit Your Story Before Time Runs Out








Share Your Best Travel Tale or Fail…

Post one short video and you could win your next vacation!

Three Easy Steps

Choose Your Video

Choose a video of your travel tale or fail that is 60 seconds or under.

Post and Submit

Submit your video at the bottom of this page with your name and email. (Feel free to also post to your social media and tag us).

Follow and Vote

Follow us (Instagram, TikTok, Facebook) & vote for your favorite tale on IG during the last week to help pick the winner!


Travel Tales & Fails

You decide whose video is the winner!

HelloVacay is introducing Travel Tales and Fails, a contest where anyone can submit a video (60 seconds or under) that highlights their best or worst travel moment. Many of these will be featured on social media—however the very best will win a week long all-accommodations-paid trip for two to one of many beautiful resorts!

Just visit this page to upload your video directly and officially enter the competition! Start your video with the phrase “This is my HelloVacay Tale (or Fail)”, or some variation of this phrase.

The best part: the community decides. You will get the chance to vote on whose tale is crowned winner—see below to check out a few destinations we’ve highlighted, where you’ll vote and how you can submit today.

You Choose Where to Go!

HelloVacay has sourced resorts at a number of amazing destinations for our contest winner, who will earn a trip for two with all accommodations paid. Our winner will choose which destination is their favorite. Below, we decided to highlight nine of our favorite spots—these are just a few of many places you could travel to.

Las Vegas


Lake Tahoe





Costa del Sol

Martha's Vineyard

And Many More…

Your Tale Will be Seen & Heard

While only one can win the grand prize of a free week-long vacation, many of your tales will be featured across our social media pages. We’ll be doing some light production to enhance these stories, and are happy to send you a copy of the video as well for your own personal use.
Frequently Asked Questions
  • When does the competition end?The competition will end on April 10 at 11:59PM Pacific Time, at which point the winner will be announced shortly after through social media and direct email.
  • How quickly will I receive my trip if I win?This will be dependent on what dates work best for you and which location you prefer, but it could be as quickly as a couple weeks!
  • What is the duration of my covered stay?The winner will receive a week-long, accommodations-paid trip.
  • How many people can the room accommodate?The room will be able to accommodate at least two people, though this varies by resort and you may be able bring more at certain locations.
  • What if I want to travel somewhere outside of your examples?Our examples are just nine out of many amazing global destinations, so you certainly can take your pick of spots that are outside of our example locations.
  • Does this include airfare?The winner will not have airfare covered, however all accommodations will be provided free of charge.
  • What happens if my stay is cancelled due to COVID lockdowns?If COVID or lockdowns interfere with your stay before you take your trip, we will find a way to ensure you get the opportunity to take the trip at a later date or take a trip to a separate location which is more open (your choice).
  • How will the voting process take place?The voting process will happen through Instagram, particularly in a series of Instagram Stories where users will be able to vote for one submission or another. This voting process will begin a few days before the end of the contest, so follow us and keep your eyes peeled!
  • Is there a minimum age?The minimum age for check-in is set by the individual hotels. The minimum age is typically between 18-25 years old, and we recommend that the winner confirm prior to confirming their reservation.
  • Who is HelloVacay? Have you done this contest before? Why are you running this contest?HelloVacay is a travel technology company and this is our first time running this contest (but probably not our last!). We created this contest as a way to build up our social media presence and stir some creativity in the online travel community.
  • How much information do I need to share to enter the contest?You only need to share your name and email (so we know where to reach you if you win).
Telling Your Tale: Tips and Tricks
When telling a short, compelling story, a little planning makes a big difference. Here are a few of our top storytelling tips:
  • Plan your story—know what you want to say
  • Tell the story like you talk
  • Be expressive and add humor or surprise
  • Leave out the details that don’t matter
  • Add a call to action—ask your followers to follow you or HelloVacay for more
  • Leave some questions unanswered, then answer it in the comments if someone asks!
  • Have fun!
Tips for effective composition:
  • Use vertical (portrait) orientation and hold your phone steady
  • Be sure that your face is well-lit. Try to use a room with a lot of natural light.
  • Be aware of your background–tidy your space or use a visually interesting background
  • Don't be afraid to use some text on your opening frame

Submit Your Story

Pack your suitcase, because once you submit there’s a chance you’ll be flying out in no time…