Must-Read Tips for Traveling With Kids (You’ll Thank Us Later!)

Must-Read Tips for Traveling With Kids (You’ll Thank Us Later!)

Vivacious, friendly and optimistic. Ambitious, hard-working and whip smart. These are the two sides of Highland Park mom Sarah Stopek Hirsch, one of Chicago’s top family travel bloggers. Recently, over a decadent lunch at Sixteen, we chatted about how she went from award-winning marketing promotions entrepreneur to starting less than a year ago. And below, she shares some of her best tips for making traveling with kids a positive experience for the whole family.

Make It Better: When did you first fall in love with traveling?

Stopek Hirsch: I’ve always loved to travel. Growing up, my fondest memories are family vacations. When my husband and I met, we traveled a ton together before having our son. Once my son was born, we were trying to figure out if we could still see the world like we liked to. The answer is, yes! It wasn’t as difficult as people made it out to be. The more I did it, the more of an expert I became and it became the topic of conversation among other families in Highland Park. We would swap tips on great places to stay and the best places to visit.

What inspired you to start

I was at a point in my career, as an entrepreneur, where I was looking for something new — a passion project — and I thought, “What was my favorite thing to do?” I loved traveling with my son, but how could I turn that into a business?

My goal with WellTraveledKids is to inspire families to travel together and be a resource that offers guidance on where to go and tips for places you’re already going. I only have one kid [Harry, age 5] so I’ve brought in additional authors with diverse families with different ages and numbers of kids to share their stories to make the site a comprehensive resource for families.

Does Harry love traveling as much as you do?

Absolutely! If you ask my son what he did on a typical day after preschool, he says he doesn’t remember. But when we’re traveling, it’s a completely different story. He can tell you in detail what we did, and he can point to a world map and show you where we went. Everything he’s seeing and learning is going to resonate and stick with him. I love traveling with my kid — it ‘s my biggest passion. If there’s a way for me to help other kids experience travel through my site, that’s even better.


It’s been less than a year since you founded and it’s amazing how far you’ve come with the site and the community you’ve built. It couldn’t all be smooth sailing though — what were some of the biggest challenges you faced?

Having been a successful entrepreneur before, I kind of forgot what the beginning stages of starting a business are. I felt so passionate that I overlooked the fact that I didn’t have a background in writing or running a travel magazine. I’ve been very fortunate in that I have 30 authors in less than a year but it’s a bigger challenge to build an audience than I would have guessed. I thought if I put great content out, people would just find it. I discovered that it takes a lot longer to build a social media presence, figure out SEO, working with real parents to tell their stories and editing some of their work — it’s all been more than I guessed it would be. It’s a 24/7 job having a magazine on the internet. I’m always thinking about it and there are always things I could be doing. It adds to the excitement and I’m up for the challenge, but there’s a lot more to it than I ever would have guessed. It looks so seamless and easy when I follow my favorite travel bloggers online.

What’s been the most fulfilling part of founding WellTraveledKids?

Seeing how travel has affected Harry made me realize how important it is for kids to have opportunities to explore. So that inspired me to give 50 percent of the profits from my site to fund opportunities for less fortunate kids to travel outside of their daily life.

I think the most fulfilling part of WellTraveledKids so far was when I had a chance to take 30 special needs high school kids from Johnson College Prep to the Skydeck and explore downtown Chicago. They were now a part of the skyline that they could see from their home every day but had never been to. And to see how my son immediately bonded with these kids that he might not have met otherwise was so touching. At the end of the day, I feel like we took as much if not more from the experience as they did. It was fulfilling to know that at not even a year in I’m moving toward the philanthropy goals of the site.

What are some of your business goals for the next year?

I’d definitely like to do more philanthropy trips, and to attract more sponsors to help fund those trips, to share more stories and tips from travel industry experts and I want to start hearing from kids in the next year, especially now there are so many high schoolers that are doing amazing trips where they are volunteering in third-world countries or backpacking through Europe. I’d love to hear their stories and how they are impacting their views on the world. (E-mail [email protected] if your kid or teen has a story to share!)

What was your first trip with Harry?

When he was 6 months old, we took a family vacation to Phoenix for Cubs spring training. We took him to Cubs games, laid at the pools and escaped from the Chicago winter. Even as a baby he was totally a pro, and because that trip went well and we planned it well, it gave us the courage to do other trips.

Do you have a most memorable trip as a family?

The trip that was most meaningful and that inspired WellTraveledKids was when Harry was 2 and we took him to Hawaii with my parents. His speech developed late and he wasn’t talking much at the beginning of the trip. After two weeks in Hawaii, he was talking so much! This is when he fell in love with maps, and he loved finding the different islands we had visited. We bought him a conch shell, and he would talk about conch shells, whales and luaus. Watching his speech develop through that trip — and I’m no child development expert — that was really what sparked my understanding of how taking a kid out of their everyday environment can really improve their overall development.


Any trips you’re looking forward to taking? 

We just got Harry his passport! Up until now we’ve stuck to travel in the 50 states. We’re going to Turks & Caicos in a couple of weeks. I was named a Beaches mom, so we’re attending the Social Media on the Sand conference. Harry was so excited when we went to the post office with him, and he can’t wait to have stamps in his passport and go to an island he hasn’t been to. He already knows where it is in on the map.

Any advice for people looking to start their own blog or business? 

I would say just do it. If you spend too much time researching it and talking to people, you’ll talk yourself out of it. Even though there are a lot of challenges along the way, there’s nothing better than being an entrepreneur. It’s an exciting life that not everyone is brave enough to explore, but those who do find the rewards are wonderful.

Sarah’s Tips for Traveling With Kids

1. Visualize every step of the way — from leaving your house for the airport to coming home. Make a list of everything you’ll need. You’re much more likely to have a successful trip.

2. Don’t overschedule. Sightseeing trips are great and it’s good to have a list of things you want to do, but just pick a couple of things you want to accomplish each day and leave the day open to see through your kids’ eyes.

3. Always call ahead and ask your hotel if they do anything special for kids. In Chicago, there are a handful of hotels like The Peninsula that go above and beyond.

4. Let hotels know if you’re celebrating a special milestone as a family. Don’t be afraid to politely ask for an upgrade.

5. When flying with a baby, you can check all of your baby gear for free — stroller, car seat — and it won’t count against your checked bags on United, American and most major airlines.

6. Prioritize sightseeing. Make a list of what adults prefer and another of what kids want to do. Do the adult activity first, and then the kid one next as a reward and they can run wild and have a good time. For example, in Chicago, we took Harry to the Art Institute and then went to Maggie Daly Park and he ran and played.


7. Lots of people wait until kids are older to take them to Disney, but kids under 3 are free, and not a lot of people know that.

8. Never underestimate the value of an off day. We find everybody bounces back if you don’t do two theme park or major sightseeing days in a row. Kids love to just splash in the pool and it makes for a more enjoyable active day the next day.

9. Rehearse ahead of time with the kids. Let them know a week ahead what the plan is. Walk through the entire experience. Surprising kids is exciting, but I’ve heard stories where it has backfired and the kids are caught off guard and it’s not as fun as the parents hoped.

10. Kids should have their own bag. Harry loves having his own suitcase and they can help carry some of their own healthy snacks, activities, toys, cards and art supplies.

11. Come prepared with enough diapers, extra clothes, snacks, bottles and emergency medication to prepare for any unexpected flight delays.

12. Splurge for help to make it a vacation and not feel like work. Hire a porter at the airport to help drag your bags or rent cars with car seats so you don’t need to bring your own. Maybe rent a spacious suite so you can spread out.

13. Ask yourself why you’re going — Is it for relaxation, adventure, sightseeing? Set goals and understand your limitations. Make sure everyone understands the goals so they’re enthusiastic about the plans.


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