Extended! With everything that is going on around the world, between an election and a pandemic, we understand that entering a photo challenge might be the last thing on your mind. However, we could all use an escape right now, and there’s something to be said about how therapeutic it can be to relive your favorite memories. With that in mind, we’ve extended our #PPOnceUponATime challenge until November 8, 2020, in hopes that you will take a moment to share, and that this experience of traveling down memory lane offers you something special. Stay well, friends. #PassionPassport


They say a photo is worth a thousand words… in this week’s #PPOnceUponATime challenge, we want to know just what those words are.

In all likelihood, one time or another, we’ve all captured a moment that embodies a great story within it. Whether you have endured a treacherous hike to catch the sunset from a mountain’s peak or have had a meaningful encounter with a stranger on the street and walked away with their portrait, we want to know the story behind your most memorable travel moments.

To enter:

    1. Share a photo/video from your travels with a meaningful or memorable story behind it by November 8, 2020, 11:59 am EST.
    2. Take us into the scene through a detailed caption describing the story behind this moment. 
    3. Tag #PPOnceUponATime and @passionpassport for a chance to be featured.

#PPOnceUponATime Guest Judges:

  1. Rebecca Ume Crook (@sticklittleleaves) / Educator & Photographer
  2. Sam Vox (@sam.vox) / Photographer
  3. Andrew and Emily (@alongdustyroads) / Travel Bloggers

*NOTE: Entries must be posted or re-posted (i.e. you cannot simply ‘tag’ an older photo/video) from a public account during the challenge period. Those posted from private accounts and/or posted outside of the challenge period will NOT be considered eligible for a feature.

We’ll announce the winner and honorable mentions the following week on our Instagram feed based on Quality of ImageQuality of Caption, and Creativity/Interpretation of the Theme.



For @passionpassport‘s #PPOnceUponATime challenge // “This trip was special for me—a trip to Rome with my parents to visit a nearby small town just outside of Rome where my father was born—a place he has not been back to for 60 years. On the day I took this photo, I wasn’t supposed to still be in the city. My parents had left to visit family, and I was on my way to the airport to head back home to London. However, I realized that I accidentally swapped passports with my mother, so I was unable to board my flight. With no choice but to return to the city, I spent the day exploring on my own. For the first time in my life, I was alone in a foreign place, and while I was somewhat anxious about it, looking back now, I truly enjoyed the experience. I shared the details of my mishap on my Instagram. My community’s response was beautiful, with an influx of supportive messages and suggestions on how to spend my new-found extra day in Rome.

As I made my way from my hotel to the area of Monti, a recommendation by one of my followers from Rome, I passed this restaurant and stopped to take a photo of its colorful facade. It wasn’t until I walked away and looked back that I spotted the Fiat parked in front, which was very unlike me to miss a vintage car parked, so I headed back to take another photo.

The gentleman pictured in the photo was standing behind the car on his own, so, naturally, I waited for him to move. When it appeared he was about to leave, I got ready to take the photo as a woman walked towards him, and they embraced. It was not at all what I expected to happen, but I took the photo without thinking twice, and it has become one of my favorite travel photos ever! Often, I find myself hesitant to take photographs with people in them, but as the saying goes: ‘When in Rome!’”

Photo and Words by @oncewaslost_📍 Rome, Italy

Check our full Terms & Conditions, and contact our Social Media Manager, Alex Ortega, at alex.o@transfer.passionpassport.com with any questions. No questions? Get going!