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Contributed photo by Stephanie Hays. Stephanie Hays, her husband, Peter Woolcock, and their 2-year-old son, Hays, pose on a roof in Bangkok, Thailand. The family is on a worldwide trip as part of a promotion called "Live Anywhere on Airbnb."

In this space in August, we told readers about a lucky Chattanooga family who won a year of free travel accommodations in the "Live Anywhere on Airbnb" contest.

Now, Stephanie Hays, her husband, Peter Woolcock, and her 2-year-old son, Hays, are at the mid-point in their around-the-world journey.

They are among 12 travel parties worldwide chosen from 314,000 applicants to participate in the Airbnb promotion. Hays is a former brand manager for Chattanooga Tourism Co., and Woolcock formerly ran an after-school soccer program here.

We caught up with Shephanie Hays recently as the family settled into a stay in Cape Town, South Africa, after spending several months in Europe. Below is a Q&A conducted by e-mail describing their travels so far.

Q: When did you leave Chattanooga, and what has your itinerary been so far?

Hays: We left on Sept. 1. We spent four weeks in Rome and then four weeks in Athens. Then we visited friends in Istanbul for a few days before making our way to Marrakech [Morocco], where we [stayed] for three weeks. For Thanksgiving, we already had plans to visit Pete's family in Cornwall [U.K.], so we'll be there for two weeks before heading to Bangkok, Thailand for one month. [We spent] the month of January in Sri Lanka. We're trying to stay flexible due to ever-changing COVID situations and restrictions. Staying safe, and keeping [son] Hays safe, is our #1 priority, of course.

Q: Did you get to pick the accommodations in each stop and have they been nice?

Hays: Yes, Airbnb's "Live Anywhere" program (we are participants along with 11 others plus their companions) is all about gaining insight into what it means to live in Airbnbs long-term. We're given a budget and are allowed to book homes in any location so long as we spend at least four weeks in each listing.

Since we choose them, they're as nice as we pick. Before this program, Pete and I had stayed at 40-plus Airbnbs in 19 countries, so we know what we like. And so far, we haven't encountered anything unexpected.

In Rome and Athens, we prioritized location first and foremost (and saving some budget for a few side trips), so our apartments were quite modest In Rome, we were right across the street from an amazing playground. We knew that when we booked but didn't realize just how perfect that would be to allow Hays to burn off some energy and interact with other children every day.

We stayed in our own riad (a riad is a type of family home centered around a courtyard) in Marrakech's medina (old city.) It was absolutely incredible.

The place we're in currently in Cape Town is from 1905 and is the first Airbnb we've stayed in where the host had actually lived, (and stays between bookings, I think), so it really feels like a home. We've been surprised at how much that's impacted our stay. I think we were perhaps a little homesick, but having somewhere homey, albeit it not "our" home, has totally scratched that itch.

We've been amazed at how well Hays has adapted, too. He calls each place "new home" for our first week or so, but other than that, seems unfazed.

Q: Have your parents (Ken and Ellen Hays, of Chattanooga joined you for any portion of the trip, so far?

Hays: Yes. My parents are trying to meet up with us as much as possible. We call them our "bonus companions" since Airbnb refers to me as the participant and Pete and Hays as my "companions" (each participant is allowed up to three). They joined us for a few days in Rome (they were already traveling in France) and in Bangkok and Sri Lanka. My dad also met up with us in Athens, and we visited some Greek Islands.

Q: Have you run into any unexpected challenges?

Hays: Keeping up with COVID restrictions is tricky, but expected. While in Marrakech and traveling to the U.K. to visit Pete's family immediately after, Morocco banned U.K. visitors, so our British Airways flight from Marrakech to London was canceled, but as soon as we heard the news, we had already rebooked with a layover in Lisbon.

Honestly, we're amazed COVID hasn't derailed us even more (knock wood!) It's certainly forced us to change plans, but we wouldn't be in Cape Town, most likely, in that case, so we can always see the bright side.

In the minor challenge category, of course we always appreciate EPB when we experience the internet speeds the majority of the world have to put up with.

Q. Without getting too personal, have the economics of the trip worked so far?

Hays: Peter and I were saving to take a year off and travel but weren't planning to go until early 2023 (at the earliest). So, when we saw the Airbnb program, we figured it was worth it to apply and speed up our plans.

Quitting our jobs is scary — although Pete likes the unknown more than me! — but this is a once-in-a-lifetime experience. Airbnb is covering our accommodation, and we're staying in much nicer places than we would have been able to our own, and they also provided a transportation allowance.

We have a massive Google spreadsheet where we track each and every expense so that we have an understanding of where our money is going and can budget accordingly. And we're trying to balance visiting places in Western Europe (that are more expensive) with less expensive destinations, like Southeast Asia. Traveling slowly, like we're doing, also means we have many evenings where we cook at home and can spread out museums and attractions over the course of the month. We're not pressed to do everything in a short period of time.

Also, we listed our own [Chattanooga] home on Airbnb, and it's been doing really well. So that has been really nice – to have some income to offset our traveling. We've been Airbnb hosts since 2012 (always a room in our home, not the whole house like now), and we really enjoy it (outside of the financial benefits.) It's so nice knowing that while we're going, others get to enjoy our home in the Southside.

Q: What's it been like traveling with a young child?

Hays: Surprisingly, traveling with Hays has been easier than we imagined. He's SO adaptable, and any of the challenges of traveling with a toddler are far outweighed by getting to see him experience so many different things.

We had originally planned to travel when he was 3 or 4 because we thought 2 years old might be too young. But this is such a fun age.

I don't think that traveling with a toddler is necessarily for everyone, but we've been pleased to realize that we enjoy travel with Hays as much as we enjoyed it without him. That wasn't necessarily a given, and you don't really know until you try it, so we're happy it's worked out that way.

Q: Have you been journaling on your blog or posting on social media?

Hays: I'm posting daily on Instagram (@awaywithhays), and we have started a YouTube channel: (or just search "Away with Hays"). We're trying to keep up with both things regularly so that Hays has photos and videos to look back on, since obviously he won't remember what a wild year he had as a 2-year-old! That keeps me motivated.

Q: How would you rate the experience so far? Has it met or exceeded your expectations?

Hays: How would we rate it?! It's absolutely a dream. It still doesn't seem real. I wake up every morning and go to bed every night (and everything in between) just so insanely grateful for this experience and this time with Pete and Hays. It is 100% a dream come true in every way assuming I'm able to get employed again at the end of the year.

My favorite thing in the world is to travel, and more specifically, to plan travel; and now I spend every waking moment doing just that. But there's literally nothing else I love to do more. When we were selected, I was humbled by how many friends said "oh yeah, that makes sense"— but it's because they know I'm obsessed with traveling. We are so, so lucky.

This interview has been edited for length.

Life Stories is published on Mondays. Contact Mark Kennedy at or 423-757-6645. Follow him on Twitter @TFPcolumnist.