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Traveling with kids doesn’t have to be difficult


travel with children

Last month we visited Hawaii for a week with our extended family and we had a great time. I was hoping RB40 Jr. would enjoy the trip and it went off without a hitch. We used to travel much more, but when we had a kid, we decided to put off traveling until he can enjoy it too. He’s 3 now and it’s so much easier to travel long distance with him.

On the other hand, my brother’s kid is not even a year old and he already been to New York, Boston, Los Angeles, Hawaii (twice), and Vancouver BC. Wow, that’s a lot of traveling for the little guy. Actually, he did very well on this trip too. He enjoyed the beach and the adults had a lot of fun with the baby.

3 is the magic number

I think 3 is the perfect age to start traveling long distance. The only thing we had to bring with us was the car seat. And we didn’t even have to lug it along if we were willing to pay $12/day to rent a car seat. My brother on the other hand, had to bring diaper, wipes, baby food, formula, bottles, and a bunch of baby accessories. It was much easier for us to pack because RB40 Jr. eats regular food and he doesn’t need special pants or anything like that.

Well… Here is a story for you. We rented a house in Hawaii because we had 8 people total. It’s much cheaper than hotels when you have a bigger group. The three of us shared a big bed and Jr. slept in the middle. One night at 2 am, I groggily pushed the soggy sheet away and thought why is Jr. drooling so much? Wait a minute, why are my shorts and shirt all wet? Wake up mama! Jr. wet the bed for the first time in his life…. This was really surprising because he never wet his bed before. We put plastic sheeting down when he was potty training, but his bed was always dry in the morning. I guess had too many activities that evening and the kid forgot to go potty before hitting the hay. Luckily, the bed had extra padding so the mattress didn’t get soaked. Now, we just make sure to remind him to do his business before going to bed.

Anyway, packing for this trip was great because we didn’t have to check anything. We all just took carryon bags and that was it.


Last year we took a short flight to the Bay area and Jr. liked it so that was a good test run. The flight to Hawaii was much longer at around 6 hours. That’s a long time for a super active little boy and I was dreading that he’d be running up and down the aisle. Surprisingly, he did really well and sat in his seat pretty much the whole flight. We got some crayons from the hostess and that kept him occupied for a bit. We read the in-flight magazines. He liked the aircraft safety card and wanted to go down the evacuation slide. We also looked at all the pictures in our great guide book – Hawaii The Big Island Revealed. He got obsessed with the lava and really enjoyed learning about volcanoes. He also fell asleep for about 90 minutes so that really helped too.

Our flight back to Portland left at 11 pm so he slept the whole way though. That was even better. One girl (4 or 5 year old) screamed her head off for like 3 hours until she fell asleep from exhaustion. Poor kid probably had an ear pressure issue or something like that. All in all, it went off much better than I expected.

Relaxing vacation

I think the key for us was we expected a relaxing vacation. When we didn’t have a kid, our vacation days were full of activities. This trip, we usually went to visit various places in the morning, and then came back to the rental to rest in the early afternoon. We went out for a short excursion in the evening a few times, but usually we just hung out at the pool and took it easy. We didn’t do long hikes or anything like that because it’s tough with 2 kids in the group.

Another big difference between 1 and 3 year old is the ability to leave our kid with the family for a bit. One day, we took a helicopter tour and the rest of the family went to explore Hilo. At 1 or 2 year old, it would have been a lot more difficult for Jr. to let us go for a couple of hours.

 Next year

This trip went really well and I’m excited about the possibility of even longer trips in the future. Next year, I want to go to Thailand for a couple of months and bring Jr. to meet all his relatives. That will be a really long flight, but I think we’ll be able to do it. I want to take these extended trips before he starts grade school because I don’t really want to pull him out of school for 2 months. I guess we could go during the summer break, but everything is so much more expensive in high season.

So do you travel internationally with your children? Please share your experience so we can be more prepared for our future oversea trips. 

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Joe started Retire by 40 in 2010 to figure out how to retire early. He spent 16 years working in computer design and enjoyed the technical work immensely. However, he hated the corporate BS. He left his engineering career behind to become a stay-at-home dad/blogger at 38. At Retire by 40, Joe focuses on financial independence, early retirement, investing, saving, and passive income.

For 2018, Joe plans to diversify his passive income by investing in US heartland real estate through RealtyShares. He has 3 rental units in Portland and he believes the local market is getting overpriced.

Joe highly recommends Personal Capital for DIY investors. He logs on to Personal Capital almost daily to check his cash flow and net worth. They have many useful tools that will help every investor analyze their portfolio and plan for retirement.
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{ 39 comments… add one }
  • darren May 21, 2014, 2:40 am

    Glad the vacation went well with Jr. Was hoping for some more details about the big island and maybe how this trip compares to Oahu. Im heading to Hawaii for the third time…first time with kids(5 & 1.5). We will leave at the end of Oct so the weather should be perfect. I definitely want to see the real Hawaii rather than the touristy Hawaii. Still planning our itinerary.

    • retirebyforty May 21, 2014, 10:06 am

      See if you can find Hawaii Revealed at your library. It’s a really good book.
      I like the Big Island more than Oahu. There are more things to do in Oahu, but I felt like it took away from spending more time with nature. You can go shopping, visit Honolulu and the Pearl Harbor, go to a laua, eat at nice restaurants, and all kind of things on Oahu. On the Big Island, we spend 90% of our vacation enjoying the beaches and volcano. It was much more relaxing.
      How long are you spending in Hawaii? I’d recommend a night or two in Hilo/Volcano village. You can go see the volcano at your leisure and see the non touristy side of the island.

  • MrsFinancialFreedom May 21, 2014, 2:44 am

    I must admit, when my little girl was a baby, I couldn’t face travelling abroad with her so just stayed in the UK and did quite a lot of camping. When she turned 4, we went on our first holiday abroad and had a fab time so I think you are definitely right in saying 3 years is about the right time to start travelling further afield.

    • retirebyforty May 21, 2014, 10:07 am

      That’s great! I’m glad we waited too. It’s so much easier now that he’s a bit older. When he was a baby it was already so much trouble going around town.

  • Clarisse @ Savvy Scot May 21, 2014, 3:11 am

    I haven’t travelled internationally with my daughter, but we had a long road travel before when she was 1 year old. It’s not difficult even if we rode on a public bus with my friends. My daughter was so good and I didn’t bring lots of things like feeding bottles because I breastfeed her for one year and 6 months.

    • retirebyforty May 21, 2014, 10:08 am

      Great! We also did a road trip with our kid when he was 1, but we drove so we could bring everything… 🙂

  • Alexis Smith May 21, 2014, 3:17 am

    Glad to hear you had fun, Joe! I agree, 3 is the magic number. My sister started bringing along her son to trips when he turned 3, and he has gotten so accustomed to it that he doesn’t run around or whine anymore when we go to long trips. We’ve never traveled abroad though, so I can’t give you useful tips. I hope you fun in your next trip! 🙂

    • retirebyforty May 21, 2014, 10:09 am

      I think 20 hours traveling would be really hard at 3. Hopefully he’ll be even better next year. That’s a really long flight. Thanks!

  • John C @ Action Economics May 21, 2014, 4:25 am

    That’s awesome that RB40 jr was able to be so well behaved on the flight. I’ve always been apprehensive about flying with children. My sister has a 7 month old and recently took her to 3 destinations across the country on a plane. There’s no way I would be able to do that. It certainly is true that once kids are potty trained, can walk and communicate they are MUCH easier to travel with.

    • retirebyforty May 21, 2014, 10:09 am

      Wow, 3 destinations. That’s nuts. 🙂

  • [email protected] May 21, 2014, 6:44 am

    We have never flown with our kids but we have driven them all over the country. I agree with you that it gets easier as they get older. We had some nightmare trips with crying babies in the back!

    • retirebyforty May 21, 2014, 10:10 am

      We had a long crying road trip to CA when he was 1. At least we only had one crying kid. 🙂

  • [email protected] May 21, 2014, 7:13 am

    I have a friend who’s daughter has traveled more internationally in her 2-3 years than I have in my lifetime! I know some who like to take advantage of the fact that you don’t have to pay for an extra ticket when they’re 18 months or something. I’m not sure my wife and I could handle the stress. We might start off with some road trips this summer for our son who’ll be about 1.

    • retirebyforty May 21, 2014, 10:11 am

      Oh yeah, I forgot to mention that. The seat is free under 2, but you’d have to hold the kid the whole flight. That’s not a lot of fun either. Enjoy your road trip! You should be able to travel much more when he’s a bit older.

  • John @ Sprout Wealth May 21, 2014, 8:02 am

    Glad to hear it was a relatively low key trip in terms of traveling with your son. We have three and have never flown with all three, but did when we had two. We’ll all be flying at Christmas, but only domestically. We have driven quite a bit with them, but think the international travel will have to wait until our youngest is 3 or 4. I agree that you really don’t need a whole lot, but when you have multiples it starts to add up. 🙂

    • retirebyforty May 21, 2014, 10:12 am

      We already have our hands full with 1. I have no idea how people do it with 3 or 4 kids. I’m sure the family adjust, but it just seems so difficult.

  • The Smaller Dollar May 21, 2014, 8:18 am

    I hate to break it to you but what you experienced might just be called luck. Some kids just can’t handle the requirements of long term air travel until they are much older. But hey whenever you get lucky don’t question it!

    • retirebyforty May 21, 2014, 10:13 am

      I’ll take luck!

  • Pretired Nick May 21, 2014, 9:03 am

    Your story was good, but it needed more puke! (:

    • retirebyforty May 21, 2014, 10:14 am

      Oh man, I feel so bad for you guys. The kids got a little sniffle, but it wasn’t too bad at all. We’re lucky no one got really sick on this trip. That’s another big problem with international trips.

  • Pura Vida Nick May 21, 2014, 9:49 am

    My wife is 7 months pregnant right now. We are planning a trip to Costa Rica in January to visit the families I used to live with there (so the baby will probably be 6 months old). My wife’s family is coming and everything – there will probably be 9 of us.

    Basically we had been planning this trip to Costa Rica since before we found out we were pregnant. After we found out, we said, ‘well I guess we can’t go!’ Then we thought about it and decided to give it a go anyway.

    Honestly I’m pretty scared, because this will be our first child. But I like diving head first into new things. Anyone have any advice? (I still have to research if I have to buy a plane ticket for our baby, or how to buy a ticket for an unborn, and how to get a passport in under 5 months once the baby is born).

    • retirebyforty May 21, 2014, 10:16 am

      Actually, 6 months is probably easier than when they’re 1 or 2 year old. I’m pretty sure you don’t have to buy a ticket for the baby. Call the airline to make sure. I don’t know about passport. Shouldn’t be that difficult, though. Good luck! It will still be a lot of fun. 🙂

  • Justin @ Root of Good May 21, 2014, 11:32 am

    We are headed out on a five week trip this summer with three young kids and this article really resonates with me. Our youngest just turned two.

    This trip would be impossible if we didn’t accept the limitations that a two year old places on our daily activities. We’ll basically be working around his schedule and will have to be as flexible as possible. We will try to take it easy and not hold to a strict schedule that’s unattainable.

    Lucky for us, we’ll have a week or so in each major destination and we can take a day off of being tourists and hit up the playground, library, or swimming pool to relax.

    It’s definitely different traveling with young kids than it is when it’s just Mrs. Rootofgood and me. We can do marathon bus or plane trips, get three hours of sleep and have crackers and water for breakfast if need be. Kids add a whole new set of constraints to travel, but it’s certainly fun exposing them to different places, foods, and cultures.

    • retirebyforty May 23, 2014, 9:14 am

      Wow, 5 weeks. That’s great. How did Mrs. ROG get that much time off? 🙂
      We had a lot of fun on this trip. It was different than what we’re used to, but it’s nice and relaxing. Have a great trip!

  • Finaciable May 21, 2014, 12:40 pm

    I agree with you on the age of three. We have travelled extensively with our children (4 &7) since they were babies. As my wife’s family lives outside of the country it was not really optional if we were going to get on a flight or not as we felt the need/obligation to visit. Eventually we took a job assignment overseas which required frequent long haul flights back home for various family obligations. Luckily our kids were troopers and knew the routine very well. We did found the hardest age for the kids to travel to be 2, the bathroom trips were difficult, they were old enough to move around, but not old enough to always understand no and had no real attention span to watch a movie, color, play games for any real length of time. The biggest piece of advice I have if you can afford it is to (i) get an car seat/stroller combo and (ii) the kids own seat. Specific car-seat/stroller combo’s are FAA approved and site right down into the seat. We would give each child a snack going onto the plane, roll them down the tarmac, collapse the wheels and sit them down and strap them in. It proved to be no disruptive to their environment and they were comfortable with their seat. During naps we would put up the hood and put a blanket over and they effectively had their own closed off space. I am convinced this saved years of my life on 16+ hour flights and inter-airport transfers. Now at the ages of 4 & 7 my kids love to fly, they now the routine, love doing their activities on the plane and most importantly know that that when in the airplane it is quiet time.

    • retirebyforty May 23, 2014, 9:15 am

      Our kid never liked stroller. I quit riding in a stroller way before he was 2. I don’t think he likes the confinement. That combo sounds good for kids who are used to stroller. 🙂 Thanks for the tips.

  • Pat May 21, 2014, 1:14 pm

    My son first international flight was when he was a month old. We prepared a lot of his extra clothes but non for ourself then he throw up on my husband:-) there were many trip, number of countries since then so we are almost a pro on traveling with kids.

    Last year my son(5) and I went back to Thailand we had such a great time. I have a real pillow carried on board with me so my son could lean on against the window to get some sleep. A small blanket is handy ,too you could make a tent like with a few paper clips so the light is not bother your kid. Also, I packed food , some milk because often, my son get hungry when we are on the way to a hotel.

    • retirebyforty May 23, 2014, 9:16 am

      Great tips. It’s a long flight. We’ll see how we deal with it next year.

  • davidmichael May 21, 2014, 2:23 pm

    Good advice Joe regarding travel with the kids. As a professional traveler for 20 years in the field of Adventure Travel, we first took our kids on a month long trip to Australia to do some scouting work when they were two and four years old. Fortunately, it worked great.

    However, in working with thousands of families on vacation trips to places like East Africa, Nepal, the Galapagos, Peru, etc., I found the magic ages to be 7 though 13. After that…leave them home because they will be totally immersed in their age group, saddled with I-Phones, I-Pads, Computers, etc, etc. I don’t know how many times I was a co-leader on a trip like a two week safari to Tanzania, for example, where most of the teen age kids whined, complained, and generally were awful so that the trip was miserable for fellow participants, parents, and trip leaders. A way out of that is to make sure to bring their best friends along so they all can share in the experience.

    Having said that, I took my kids with me through the teen years into their 20’s as special gifts for graduations or completing medical school, etc. We still travel together now as they are in their 40’s and 50’s with their own kids. In general, however, teens can bestow upon unsuspecting parents challenges that one cannot imagine.

    Happy Travels!

    • retirebyforty May 23, 2014, 9:20 am

      I’m not ready to deal with a teenager at all. We’ll try age 4 to 13. After that he can vacation with his friends. 🙂
      I’ll try to travel more while he’s young. Maybe he’ll still like traveling when he’s a teenager like your kids.

  • papadad May 21, 2014, 8:58 pm

    Been traveling / living abroad with my kids since they were infants. It’s great now that they are well into their teenage years. They have confidence to travel anywhere in the world. When younger, they knew how to pack their own bags, prepare their own “bring on the airplane” toys and gadgets and snacks, and knew not to complain about the many long haul international flights that would happen. They also knew their role – to carry their own bag, to help mom load and unload the suitcases, to stay together and watch out for each other intransit at airports, etc.

    Teaching kids how to travel is more than getting on an airplane — they learn how to entertain themselves, how to deal with uncertainty, ambiguity, and deal with sudden changes that occur during traveling, eat different foods and not go hungry, try new things, on and on and on…. great life skill – almost as valuable as learning a new language.

    Mostly, looking back, I see my boys have learned how to adapt, learning to problem solve, and of course appreciate and respect others cultures – that truly differentiates a “well traveled” versus “home body” kid.

    I’ve lived it/ see it first hand and it’s amazing.

    • retirebyforty May 23, 2014, 9:21 am

      Thanks for sharing! Your kids sound amazingly mature.
      We’ll try to travel more in the years to come so our kid will be well traveled too.
      For now, his only job is to stay calm during the flights. 🙂

  • No Nonsense Landlord May 22, 2014, 7:03 pm

    Hawaii is the greatest! It’s too bad it is so expensive, and so far away.

  • 1stuhave2findthetunnelb4ucthelight May 22, 2014, 7:08 pm

    Traveling with a young kid definitely makes you more tolerant when someone has a baby that won’t stop crying, etc. It will create instant empathy. We had mostly good flights, but a few that were a challenge, so pretty much luck on those things.

    Good to travel for free when they are under 2 to visit family/friends when the flight is free. Make sure you sit on the side of the plane that the flight attendants can’t see you in their direct line of sight. Makes it easier when your kid won’t cooperate and sit like an adult in the seat/your lap without the flight attendants going all safety conscious on you (as if holding a kid in your lap is safe).

    Probably worth considering is how old to take kids on trips related to how long they remember the trip in the 1st place. Seems like the memories fade before mostly five years old. Many great memories for us, my son now around 10, seems to be forgetting some of the trips/places we went when he was younger than 5. Recently, there was that couple in San Diego that was going to sail around world or something with very young kids with thought kids would remember the experience etc. Ended up being a huge tax payer rescue with Coast Guard/Navy as the baby was significantly sick. Ironically, just like the rest of the trip, the kids will also forget the rescue when they get a bit older….

    • retirebyforty May 23, 2014, 9:24 am

      I just heard that story on NPR. It would have been an amazing adventure, but it just didn’t turn out well.
      We’ll take a lot of pictures so at least we’ll be able to see that. My long term memory is terrible. I don’t remember much at all before I was 10. Mrs. RB40 on the other hand seems to remember everything. I guess everyone is different.

  • Pauline May 28, 2014, 8:27 am

    They have to get used to it from a young age. If you saw babies in Guatemalan public buses, they go 8 hours in their mum’s arms like nothing. If they cry a little, they breastfeed and that’s it. I have two sets of young cousins, one is used to long car travel, flying, etc. they know how to entertain themselves, even the 3 year old, and the other set is car sick, plane sick, any travel takes twice the time for cleaning and comforting them. The sooner you start, the better.

  • Valerie October 20, 2014, 2:26 pm

    Great post! I’ve traveled with children before, and it can be fairly easy. It’s important to have entertainment for them whether you’re flying or driving. Thanks so much for sharing this!

  • David August 5, 2015, 9:51 am

    My own daughter 1st intercontinental airline flight had been as soon as he / she had been 30 days old. Most of us organized many their further clothes although no with regard to our self then he give about my husband: -) there was many journey, volume of nations around the world after that therefore we have been virtually an experienced guitarist about traveling having young children.

  • JohnMark August 7, 2015, 11:06 pm

    Been voyaging/living abroad with my children since they were newborn children. It’s extraordinary now that they are very much into their high school years. They have certainty to travel anyplace on the planet. At the point when more youthful, they knew how to gather their own particular sacks, set up their own “bring on the plane” toys and contraptions and snacks, and knew not to whine about the numerous whole deal global flights that would happen. They likewise knew their part – to convey their own particular sack, to help mother load and empty the bags, to stay together and watch out for one another intransit at airplane terminals, and so fort

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