Ryan Sager
The Sager family in Switzerland.

Meet: Ryan Sager, Expedition Co-Founder and Media Entrepreneur

Before Ryan Sager and his wife, Emily, had their daughter, friends and acquaintances warned him that parenthood would doom their travels. 

“People were so negative and so insistent,” he said. “But it didn’t seem like it had to be true.”

He resolved that their family would be an exception. “We were going to travel aggressively,” he said. “We weren’t going to wait three or five years to get on a plane.” 

When their daughter, Sarah, was six months old, they road-tripped from New York City to French Canada. Her first plane trip came soon after.

Now 6 years old, Sarah often takes the lead on hikes, pushing her parents farther than they’d otherwise go. And Ryan—a former editor at The Wall Street Journal and Time magazine—has created The Expedition.

“I thought parents should have a place that tells them it’s absolutely possible to travel,” he said. “That gives them moral support and practical support, all in one place.”

Ryan shared his secret for booking a vacation rental that over-delivers, how his family finds under-the-radar destinations, and his take on the worst aspect of traveling with kids. 

Before we had a kid we traveled…

extensively and adventurously. We drove the Dempster Highway in the Yukon. We went to Patagonia. We did a lot of long hikes, a lot of nature. We do less stuff now where we’re 100 miles from civilization. 

The main thing that changed after we became parents is…

now we stay almost exclusively in vacation rentals instead of hotels. Especially when Sarah was littler, we needed the space and didn’t want to be worried about her being up crying with people in the room next door.

The secret to a successful vacation rental is…

digging deep into the reviews and photos. You have to get good at understanding what a real estate photograph looks like rather than a realistic one. A great sign is if reviews say “it’s so much better than the pictures,” or “the pictures don’t do it justice.” I also check the location on Google Maps if I can, and if the house has a name, there’s usually a separate website for it somewhere, so I check that out, too.

The worst part of traveling with kids is…

the cab ride home from the airport. Everyone’s tired, you’re coming down from the vacation. The exhaustion can make Sarah carsick. It’s a real failure point.

On our bucket list are…

so many destinations in Asia. We haven’t really explored that part of the world and there are so many places I’d like to visit. Taiwan, Thailand, Tokyo. I almost took a job in Hong Kong when I got out of college, but I’ve still never been there. Maybe when Sarah’s a little older.

When we travel we always seek out…

less touristed parts of the world. In Chile, one of the nicest trips we took was to the lakes region—it’s a little more obscure than the desert and Patagonia. One of our favorite parts of Italy is Emilia-Romagna. People don’t really speak English, and it’s well-priced. In Switzerland we were in Graubünden, in the far east. It’s an area where people speak Romansch, and foreigners don’t visit very much. We have this book I love, Off the Tourist Trail, that suggests alternatives to popular destinations.

I try to bring home from our trips…

something local, an artifact of everyday life. In Chile we bought an old-style license plate. I encourage Sarah to find little things that will last longer than a generic toy. We rode the Chocolate Train in Switzerland and she has a little tin train from that trip.

To keep our daughter busy in restaurants we…

have drawing contests. She draws a picture and one of her parents draws a picture and we have “blind judging.” She has an unblemished track record. We get very creative about how we mock the other parent’s drawing.

The pain points for traveling with an only child…

are similar to the overall existence of an only child. She often looks for us to take the role of playmate and honorary sibling, and she wants that participation in games and fun at all times. With a sibling she might be off doing her own thing. But we benefit from the lack of fights. And now that she’s 6 and self-contained and wheels her own bag, it seems super easy to travel with her. 

Sara Clemence is a freelance journalist, formerly travel editor for The Wall Street Journal and news director for Travel + Leisure. She's the author of Away & Aware, a guide to mindful travel.