Little C’s Traveling Friends: Traveling The World With Children For the Past Five Years

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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 get to share 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  Here is a story of another awesome traveling family!

Jennifer and her family are world travelers who aren’t afraid to go the distance with their kids!  She writes the blog, Miles, Points and the Pursuit of Travel, and has shared some of her tips about their trips and how to survive traveling long distances with children in tow.

I would highly recommend checking out her website as she does a great job of going into detail about their air travel, hotel stays and activities.  She does a cost analysis for her trips and lets you see exactly how much using points and miles helped her family!

maldvies ward

Our traveling background is extensive and began well before we had little ones to chase. We have been fans of Flyertalk for many years (mostly lurkers) and began traveling through mistake fares.  We were able to take advantage of super cheap fares to Cyprus via Rome and New Zealand in business class due to these mistakes. In fact, we got engaged in Rome in 2006 and took our honeymoon to New Zealand in 2007, which would not have been possible without those “fat finger” mistakes.

We’ve also dabbled in so called “fuel dumps” and getting bumped from flights for vouchers for future travel. But our pursuits for cheap travel hit a whole new level once the kids arrived. We naturally migrated our efforts towards credit cards sign up bonuses in order to support the travel needs of our growing family. Neither my husband nor I travel at all for work, so we rely solely on these sign up bonuses to make our travel dreams come true. So far, the benefits of having two people sign up for 2-4 cards every three or four months have given us enough miles and points for our family of four to travel two or three times a year for a fraction of what it would have cost otherwise!

Our kids are now almost 5 and almost 3 and our lives are crazy. My husband and I both work full time jobs and have significant commutes to work. It seems we’re constantly running from one place to the next during the work week, so we very much look forward to and cherish our trips together. It gives us a chance to slow down and just enjoy one another outside of life’s demands. We wouldn’t trade our adventures together for the world. Traveling with little ones can be a challenge (airport screening seems to always be the biggest hurdle of the entire trip!) but the challenges are temporary. Our kids understand that they are not able to get up from their seats when the seat belt light is on, and they are not able to use some of their electronic toys on the plane until they hear the “ding.”

Our latest adventures have taken us to St. John USVI, Scotland and England, Bali, Hawaii, the Maldives, and United Arab Emirates. While we definitely prefer to travel in business class, we will withstand economy class if the total travel time in the day is less than 6 hours. This enables us to maximize our miles, especially with American Airlines. Maximizing stopovers has been key to stretching our miles as far as possible. Our St. John trip connected onto our Scotland/England trip via a 3 month stopover in our home airport. On the return, we worked in a stopover again at our home airport for 9 months and then connected onto our flights to Kauai so in total, we traveled from the Virgin Islands to Boston to Scotland to Boston to Kauai for 40,000 miles per person round trip. This is one of the best lessons I’ve learned while redeeming miles – maximize stopovers!


St. John

That said, there are also opportunities that are too once in a lifetime to worry about stopovers, etc. Our recent travels included a trip this past fall to Dubai and Abu Dhabi for the Formula 1 race there.

camel in abu dhabi

While we were able to use the return flight from Kauai to stopover in New York before continuing onto Dubai for two of us using US Airways miles on Austrian Airlines in business class, we didn’t have enough miles to do that for all of us. So my husband and son utilized our Membership Rewards via ANA to book tickets on the same Austrian Airlines flights. This is where we learned one of our most expensive lessons in redeeming miles… I had gotten complacent with trusting the taxes that the ITA Matrix provided as part of an itinerary. When redeeming with ANA, the taxes quoted were significantly higher, but I wanted to make sure we got seats on the flights we wanted so I figured I’d just pay the taxes and get the difference refunded at a later date.  Oops.  ITA was wrong, and the taxes I paid mirrored exactly what Austrian showed on their website. Lesson learned!

Burj al Arab

Burj al Arab

We are also recently back from the Maldives. We had planned on that being an adult only trip as we had wanted to try Etihad’s business class and we thought they would only open up two business class seats per flight. However as fate would have it, when the booking window opened up, I noticed that there were four award seats on the flights we were interested in. So, I talked it over with my husband, and we decided that we really do enjoy trips more when we’re all together so the kids came with us. We managed to leverage Avios in economy for a great value to Europe and then American Airlines miles on Etihad in business to the Maldives via Abu Dhabi. We also were able to take advantage of our Hilton points before the huge devaluation in the Maldives. It was amazing! One of our most memorable vacations yet!

ward in maldives


jward in maldives


Our crazy year of travel isn’t over yet with a trip to Costa Rica this spring and an extended family vacation to Europe this summer. We’re traveling like crazy right now as our son starts Kindergarten in September, and we won’t be traveling much once he’s in school and on a school schedule. It’s been hard to keep up, but we’re having a blast!

Some pieces of advice for travel with kids:

  • In general, I would venture to say that we are more adventurous than the average family when it comes to traveling the world with our kids. However, I am pretty particular in the destinations we choose right now, based upon their ages. Do your research into medical facilities, transportation, etc. to ascertain whether or not a particular destination is for you. As they get older, we’ll expand our list of acceptable destinations, but for now, there are plenty to choose from that meet our current criteria!
  • Always consider getting bumped if the airline needs volunteers to take a later flight. Most of the time it may not work for your family, but we’ve been bumped in the past from a connecting flight that allowed us to connect in a different city to catch up to our original itinerary. We got home at the same exact time, but each had $600 vouchers in our pockets for our “inconvenience.”
  • When flying domestically with an infant (child under 2), do your homework on the passenger loads of the flights. We were never willing to fly more than an hour with one of our kids on our laps, but never bought them a domestic ticket (other than to Hawaii) as we flew on flights that were not full and the kids always got to sit in an empty seat. Worst case, you can gate check the car seat if the flight for some reason it fills up last minute, but we never paid for their flights domestically when under 2. This worked for us on domestic flights, but we never risked it on international or longer flights.
  • Kids adapt better to new time zones than adults, so don’t be afraid to travel outside your time zone. That has never been a problem for us!
  • Always, always plan ahead when redeeming miles, especially for a family of four or more. There are airlines that do open up 4+ seats in business class (and even more that open up availability for 4 in coach), but it takes lots of research and perseverance to find them. Flexibility is key and if you find the seats, take them. Most of the time you can cancel at a later date for a fee (or free if there is a schedule change, you have elite status, or if you are flying Southwest) and the likelihood that that many seats will remain available is very slim. Check several times a day if you can! Availability is always changing!

In short, taking off around the world with kids can seem like an overwhelming undertaking, and at times, it is. However, the difficulties are always short lived and I can say, without a doubt, that the experiences they are having are helping them become well rounded citizens of the world.   My family has miles and points to thank for that!

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  1. I love to hear about family travel like this! Great that you are able to go to so many places and create those wonderful memories.

    Don’t let kindergarten derail all of your off-season travel plans. We pull our elementary-aged kids out of school once a year for a week with no problems. My oldest is in 3rd grade and still hasn’t had a problem getting caught up with school work. We will probably not pull out of school when he gets into middle school, though.

  2. I have a very similar family travel philosophy – we travelled extensively (domestically and internationally) before and after our daughter was born. As kids get older, it is not just school that gets in the way, it’s all their activities and commitments. But family travel is still worth the juggling and challenges. I’ll be checking out your blog to pick up some destination ideas and tips! Thanks.

  3. Great post!

    You mentioned maximizing award bookings via stopovers….”we traveled from the Virgin Islands to Boston to Scotland to Boston to Kauai for 40,000 miles per person round trip”…..have you done a post about this topic before?
    I follow the different BoardingArea blogs, but can’t recall a post about this topic, maxmizing stopovers, focusing the stopovers on your hometown.
    BTW, was your above mentioned routing booked with UA MP miles?

  4. This is really awesome! I am curious what your travel plans are as your kids start school. One major vacation each year abroad or to a faraway state during the summer and a minor one (i.e. road trip). I somehow feel the family road trip is a classic American vacation type trip that every kid should experience at least once.
    In addition, do you think it makes a difference to your kids that they’re travelling with their sibling? Is it easier to manage them or harder?

  5. I love seeing famililies who travel together! We love to travel with our kids, but have not been brave enough to embark on trips like these. Thanks for the information – I will be checking out your blog for additional information!

  6. Hi Joey,

    Yes, our plans for next year once our son is in school include two trips – one to Bora Bora and one to Australia. Both will occur during school vacations although we’ll likely have to take him out of school for a couple of days on either end of the vacation.

    And we totally agree that a classic American vacation is in our future. We love National Parks and getting out West to visit more is definitely on our list!

    For our family, traveling with siblings make life so much easier for us. They are now at the ages where they entertain each other well and they seem to love to see new places together.

    Thanks for your questions and feel free to ask any others that you may have! We returned from Costa Rica yesterday so I’m working on posts about that adventure! Pura Vida!

  7. Great recommendations.

    Any suggestions on which airlines are best to score 4 business seats far out? I’ve only really seen Cathay, maybe VA.

  8. Wolfgang – Unfortunately, a couple of weeks ago American Airlines took away the stopover benefit so we won’t be able to maximize that with AA anymore. However, we still utilize stopovers with United, ANA, and USAirways. In fact, we’ve utilized stopovers on our three most recent trips. I plan to write about stopovers with those airlines soon.

    TravellingRabit – We have secured 4 business class seats on Austrian Airlines, United, Etihad, and Copa Airlines. There are others, but those we have personally traveled on.

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