Little C’s Traveling Friends: 5 Year Old Ilana and 9 Month Old Evie

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While I am always happy to share my own traveling stories with my family, there are tons of other great traveling families out there with kids of different ages, different numbers of kids, and who have had different experiences than me.  As part of my “Little C’s Traveling Friends” series, I am sharing different family’s stories so we can all learn from their experiences.  If you would like to be a part of this series just shoot us an email at

First, can you tell me a little bit about your family?

I am a freelance writer who focuses on travel and credit cards, while my wife is finishing her doctorate in pharmacy. We are by nature a traveling family.  I grew up in Atlanta and have family up and down the east coast, so it was common for us to take family vacations within a couple hours flight of home. While we live in Denver now, it is also a major city in a rural region, so we still have to take to the skies to see our family around the country.

My wife Janna has spent roughly equal parts of her life in Russia, Israel, and in the United States, and we try hard to visit our friends and relatives in Israel at least every other year. And since we both grew up traveling to some extent, it only seemed natural that we would take along our kids. We have a 5 year old named Ilana who recently became a big sister to Evie, who is now nine months old.

Sounds like an interesting family!  How has your traveling pattern changed (or not changed) since you have had kids?

As our family has grown, our accumulation of points and miles has kept pace, so we haven’t had to curtail our travels as much as we feared. These days, every family trip is designed around the kids, but it is not as bad as it sounds. We try to avoid very early or late flights, visit children’s museums instead of history museums, and always try to meet up with other families who have kids. Overall, we keep our travel at a slower pace with the kids, and we try to not change hotels as often as we would otherwise. With all the extra baby gear to pack and unpack, it is easier if we just base ourselves in one place for as long as possible.

Where all have you traveled with your children, and what have been some memorable experiences on some of those trips (both good and bad)?

Ilana has five years on her little sister, and definitely has been on the most trips with us. We have taken her to visit family in New York, Atlanta, Ft. Lauderdale, and Los Angeles, but also on weekend getaways to San Diego, Albuquerque, and Austin. Her big vacation that she still talks about was a trip to St. Thomas three years ago. In addition, she has now been to Israel with us three times, with a fun stopover in Italy while returning from out last trip. We stayed at an agri-tourism lodge on a farm near Parma and enjoyed locally grown food from the region. It was great fun to tour wineries, explore castles, and to see how Parmesan cheese is made. And to top it off, we flew home in part on a Lufthansa A380 in business class.

Last summer, when it was still only three of us (Evie was well along the way, but not with us yet), we all flew to Seattle and joined my parents on a train trip to Los Angeles. We took the Amtrak Coast Starlight train 36 hours to Los Angeles, and it was a big hit with Ilana. We all enjoyed bedroom accommodations with a private bathroom and a shower. Compared to first class airline seats, it was truly luxurious. The food was included, but so-so, yet the views were spectacular!

This winter, we decided to go big for Evie’s first trip. We spent took two weeks to visit family in Salta, in northern Argentina, with stopovers in Ft. Lauderdale and Buenos Aires. In Salta, Ilana spent a week playing with her cousin, while we all toured the area, hung out by the grill, and played with Evie. At five months old, Evie traveled exceptionally well, while at five years old, Ilana is already a pro!

But it isn’t always as fun as it sounds. Our worst experience was probably when Ilana got sick on one of the Israel trips. It was just a common cold and a fever, but it took her two days to get over it. All we could do is huddle in our room and wait for her to get better, and it was much more difficult to comfort a sick child while we were away from home.

What are some tips for traveling with kids that you have learned along the way (gear, where to sit on the airplane or train, choosing hotels, destinations, flying or riding the train with infants, etc.)?

Our philosophy is to travel light and work as a team. For example, one of us will get dropped off at the curb with the kids while the other parks the car, so we don’t have to schlep everything across the airport. And if renting a car at a distant lot, one of us will claim the bags and go to the curb while the other gets the car. It saves us so much time and effort.

With infants and toddlers, we keep things light by using the most compact strollers we can find that still have some storage space. With infants, we use the Baby Trend Snap-N-Go with a car seat. For toddlers, Baby Trend also makes this really compact stroller that has probably flown over 100,000 miles with us and still works great. And at around $50 each, they are much less expensive than the SUVs of the stroller world. When folded, they are so compact that we have little trouble fitting them into a rental car. On board airplanes, we’ve had good results with the CARES harness when Ilana was between the ages of two and four.

For non-stop domestic flights, we will gate check the stroller, but if we have a close connection or need to clear customs on arrival, we check it through and carry our kids. We learned the hard way that it’s no fun to wait for gate-checked items when we need to hurry to catch our next flight or we don’t want to be the last in line at customs. That is why when it comes to choosing seats, we like to be as close to the exit as possible. On widebodies, I found that it is usually the second door on the left. We board and exit quickly by only carrying on a backpack/diaper bag (that can fit in the stroller’s storage basket) and one standard roll-on suitcase.

As Ilana grew older, she started carrying her own toys and books in a small backpack, and that helped her to become part of the team. And while we restrict television time at home, we always bring a laptop and let her watch movies on the plane. Also, be sure to contact the airline and let them know that you are traveling with children, as they sometimes offer special meals for kids and even gifts (this is much more common on foreign airlines than on US airlines). For example, Ilana now has so many toys from Lufthansa, that she us recently informed us that they are her “favorite airline.” My wife and I had a good laugh, and we couldn’t help but agree.

When traveling with an infant, I like to advise people to do whatever they can to avoid lap child fees. With most airlines charging infants without a seat 10% of full fare ticket, the cost can be outrageous, especially in business or first class. I did a lot of research in this area for this article I wrote for The Points Guy. In our experience, small infants work well as lap children in coach, while large infants do fine in business and first. The rest should probably have their own seat.

How do points and miles figure into your family travels?

When my wife and I first went to Israel together in 2006, it cost us $1,500 each for a long and uncomfortable flight in coach. We knew that we couldn’t regularly sustain that expense, especially as our family grew. So we dove into the world of points and miles. We scrapped together enough miles from credit cards, business trips, and promotional offers so that we could make our next trip in business class, using United miles for a partner award to Tel Aviv, something we could never afford to pay for. Ilana was less than a year old at the time, and we were positively giddy when three Lufthansa flight attendants assembled a bassinet on the bulkhead and made up the bed with fresh linens. Think of it like Lufthansa’s first lie flat business class product. Then, we burst out laughing when they rolled a desert card down the aisle. We were definitely “kettles” back then!

Today, we enjoy a Southwest Companion Pass earned largely from their 50,000 point credit card sign up bonuses, and a wealth of other points and miles acquired through manufactured spending. Southwest is definitely our preferred carrier within the U.S., as their program takes all the stress out of finding award seats. With no bag fees and no change fees, it is a no-brainer. But when we want to go overseas, it is a huge challenge finding three award seats together, especially in business class. For example, we cobbled together our Argentina trip by using miles from Southwest, British Airways, and American. Eventually, we will probably have to travel two each on different award itineraries, so we are savoring our flights together for now.

And while we are too busy at home to gallivant around the world like some single travelers and childless couples do, it is nice to know that our travels are limited only by our time and energy, not the cost.

What future trips are on your horizon?

We are going to Hawaii in June, to celebrate Ilana’s graduation from kindergarten, and my wife’s graduation from pharmacy school. We have first class seats on United’s non-stop flight from Denver to Maui, and a week at the Hyatt. As I write this on May 1st, it is snowing hard in Denver, so you can imagine how excited we are!

Last year’s train trip was so much fun, that we will ride the rails again from Denver to Lake Tahoe this August. My family used to take ski trips there when I was younger, and I am excited to go back and experience it in the summer. From there, we will fly to Portland Oregon, and visit the nearby Evergreen Aviation and Space Museum and Waterpark. We want to see the Spruce Goose, and ride the waterslide out of the Boeing 747 perched on the roof. And later this year, we will have the opportunity to introduce Evie to family and friends in Atlanta and Israel.

What would you say to other families that are nervous about the logistics of hitting the sky (or road) with the little ones?

First, timing is everything. We have found that traveling with an infant is relatively easy when they are between 3 and 6 months old, but it became much harder between 6 months and a year when they can’t walk yet, but are constantly grasping for everything. That is why we took Evie overseas at five months old, but we realize it would have been much harder at nine months. Once children start walking and are out of diapers, they can become little helpers and be a lot of fun.

Next, I would say “look at the bright side!” Families actually enjoy many benefits when they travel by air. For instance, some airports such as Atlanta offer priority security for families traveling with young children, and the TSA always lets both parents and young children walk through the old style metal detectors rather than the nude-o-scopes. Also, airlines like Southwest offer priority boarding to families (between A and B groups), and some countries such as Argentina and Israel open up a special line at customs for families with kids. With all airlines, car seats and strollers can be checked for free, and we occasionally avoid bag fees by placing a few items in a duffel bag underneath our car seat. And besides, sitting next to a five year old is the next best thing to having an empty middle seat. In fact, when I traveled to the Freddie Awards last week without my family, I felt like I had suddenly lost my elite status!

Like many, my wife and I have traveled extensively before we had kids and we had gotten a little bit jaded by the experience. But the best part about traveling as a family has been experiencing everything again for the first time through the eyes our children.

Thanks so much to Jason and his family for sharing some of their tips and stories.  Happy travels to this family on all of their upcoming adventures!

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  1. Row, I think you just said hi to him! 😉
    Shaquanna, I couldn’t agree more – glad you like them!

  2. Holding aopa pilot magazine, flying commercially should seem cheap! But it sure is fun piloting yourself (and kids)! No TSA. No screaming at the gate that “I want to get on the plane” (our almost 4 year olds current reaction to seeing plane and not being on them). Etc.

  3. I confess to holding a pilot’s license (com, CFI, multi etc), and as much fun as it is to fly private, it is generally more expensive than flying commercial. And once I started in with the points and miles game, there was no going back.

    Thank you so much MP for giving us the opportunity to share our story! Ilana was so thrilled to see her picture on the Internet!

  4. Our Southwest flight was just a domestic leg DEN-FLL to position us for a LAN flight out of MIA. Sadly, their More Rewards program doesn’t provide that much value.

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