Day Dreamer – Cindy Bailey of My Little Vagabonds

Cindy Bailey, writer and blogger at My Little Vagabonds, is a Day Dreamer; she decided to make her dreams a reality by making travel an integral part of her family’s lifestyle. After about a year through various countries in Europe and many national parks in the USA, Cindy and her family are currently traveling through Southeast Asia for the next year or so. Cindy and her husband have two kids, ages 10 and 4, and are originally from the Bay Area, California.

If Cindy can live out her family travel dreams, so can you. Read on to see how Cindy manages finances, schooling, and the fears and logistics of traveling with children.

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Looks like you’ve been on quite the adventure around the world for over one year already…Why is your family on an open-ended trip?

The lives we were leading in Silicon Valley, California beforehand did not feel like our own. We felt heavily burdened by the routine and obligations of our daily lives, and we were often busy, stressed, and tired. Also, my husband, Pierre, and I had struggled to have our children, and now that they were here, we wanted to spend more quality time with them while they were still young. (We all know how fast kids grow!)

Although we lived comfortable lives and took great, active vacations, we felt we needed a bigger, more dramatic change.

So, we planned and then embarked on our trip around the world! By doing so, we reclaimed our lives and started to live with much more intention.

We should be able to travel for up to two years on our budget with our savings. However, from the start, we weren’t sure we would end up back in California again, which is why we let go of 90% of our possessions before we left, and we figured if we worked part-time as we go, we could continue our travels for longer, and that suits our family really well!

Both my husband and I love discovering new places and people, and having new, cultural, off-the-beaten path experiences, and then sharing all of that with our kids, for their own education, personal development, and fun. We’re also very active and take opportunities to go scuba diving, snorkeling, jungle hiking, elephant trekking, paddle boarding, and more. (We actually brought our inflatable paddle board with us to Southeast Asia!)

What’s best is that we get to choose what we do with our days: where we go, how long we stay, what activities we do, and how we respond to people and situations (travel tip: perspective and attitude are very important!) We also recognize what an incredible blessing and opportunity it is to live this way, and we really take no day for granted.

We choose to travel slowly so we can really get to know a place and its people, and we are having the time of our lives. Why wouldn’t we want to continue living this way? It suits us.

In truth, we are half searching for a place in the world we might live six months of the year, and then travel the other six months. We haven’t found it yet, but if/when we do, we’ll know it.

The only negative is that we do miss our friends sometimes; the kids especially miss their friends. Even though, we are making new friends all the time.

Julien in Tuk-Tuk

It’s intriguing that you have been able to travel for so long and continue to do so…How do you fund your travel lifestyle?

In our case, we saved up for a couple of years and are traveling both on that savings and stocks my husband received from the company he worked for. So, we keep one eye on the market.

Although my husband had to quit his job as a manufacturing engineer to travel, I am able to work on the road. (I work primarily as a content strategist and writer.) Although I chose to mostly not work the first year of our travels (except on our travel blog, of course!), I plan to work this year.

At Stream

Since you have kids that have a relatively wide age gap, how do you handle their education on the road? Homeschooling, local schooling? What are some of the best educational resources you use while traveling?

Good question! Not only are our kids at different ages (now 10 and 4 and a half), but they also have different personalities and learning styles. Although I did a lot of research on homeschooling before we left, it still took a couple of months of experimenting to find our groove for our kids and as a family for homeschooling.

For our son, the 10-year-old, who also has ADHD, we knew that anything that even looked like regular schooling to him would fail. We also wanted to motivate and inspire him to learn, not force him. In the end, we figured out that he learned best through interactive computer programs (like ST Math) and real-life situations, such as calculating the currency exchange.

In addition to math on the computer, our son does a lot of reading (only books he’s interested in, though, like Harry Potter), practices his French with his dad, and has to write reports on our excursions. Outside of that, we build the science, social studies, and history based on his interests and where we are and what we’re doing. For example, in Geneva, we visited the U.N. and in Ho Chi Minh City (Saigon), we visited the War Museum and the Cu Chi tunnels, and our son had to write and present reports on these.

Our 4-year-old daughter, on the other hand, works very well with structure. She also happens to be advanced for her age so I’ve started her on a kindergarten program using for learning to read and ST Math for math. We also read to her and she reads simple books to us.

Both our kids are required to say please, thank you, hello, and good-bye in the local language wherever we are.

Generally, my husband manages our son’s learning, and I manage our daughters. On average, we homeschool about three days per week, and have excursions (or learning-rich field trips) on the other days. So, they’re really learning all the time.

For the many online resources we use, see our list.

What was your biggest fear before you started these trips? How did you overcome that fear?

I have to really think about this. Once we committed ourselves to doing the trip, we didn’t have so many fears about it. We were ready. My husband did have concerns about whether our budget would hold us for the length of time we wanted to travel. He alleviated that concern by paying close attention to our spending in the first six months while keeping an eye on the stocks we relied on.

Now that I think about it, before we left, I had worries about two main things: adequate health coverage and keeping our kids safe while traveling (what happens if they get lost in a crowd? Or have an accident?). Like most of these types of fears, getting information, planning ahead, using common sense, and keeping fears in perspective will alleviate them. For health insurance, we use World Nomads with a backup plan for what we’ll do in case we get something they don’t cover. For keeping our children safe, I’ve written a blog post on that!

on Boat

By actually living your dreams, what have you learned about yourself and your family?

I think the main lesson we’ve learned (which on some level we already knew) is that change is hard, but once you have journeyed through it, the other side is as beautiful as you imagined it would be, and more than worth it! The experience of realizing a dream teaches you confidence and helps you grow: you’ll face other challenges with greater ease and assurance. And you get to skip regrets later.

Also, once you make the commitment to do something–and make it real by resigning from a job or announcing it to friends, for example–everything really does find a way to fall into place.

Big surprise: we don’t miss any of our possessions! With only a couple of toys each, the kids mostly use their imaginations to play, and they’ve learned to play really well with each other, as well as with others they meet.

More personally, we learned that we do need a break from our kids sometimes. Being with each other 24/7, it’s also important that we respect each other’s needs. We go sightseeing mostly for us, but visit waterparks and amusement parks mostly for the kids. I need time to myself, and my husband (who is the cook in our family) needs me to stop picking the food out of the plate with my fingers all the time. He also needs his down time.

We also learned more about the kind of travelers we are, that we love getting to truly know a place and spending quality time with locals doing as they do (taking buses, going grocery shopping, getting our hair cut), getting a rich, cultural experience in the process. (We have made so many new friends on the road!)


What’s your advice for parents who want to travel meaningfully with their kids, but never actually do?

Take a good look at the fears and reservations that are stopping you, write them down if you need to, and then eliminate each one. Most fears disappear when you put them in perspective. And for every problem, there is a solution. It might be a crazy, out-of-the-box solution, but it’s there. Instead of telling yourself why it won’t work, ask why it will, or what will make it work. Have no travel money? Stop buying things, save, sell everything, or teach English on the road with your kids as you go. If you really want to go travel with your kids, you will find a way to do it. And it will all be OK. It will work out!

And you should go travel with your kids, because the experience is so enriching, for you and your family. And you should also do it as soon as possible. Why? Because, as you know, we are only guaranteed today. Anything can happen tomorrow. When a good friend died of breast cancer, and certain relatives lost their health, I was reminded how precious our time on this earth is. As the cliché goes, time waits for no one. We really do need to seize our days and drink as fully from them as we can now.

About Cindy Bailey

CindyPhotoIn addition to having massive travel adventures with her family and writing about them, Cindy Bailey is co-author of the Amazon top-selling book, The Fertile Kitchen® Cookbook, and her fertility story has been nationally televised on NBC and CBS. Cindy is also a former newspaper reporter, freelance writer, and award-winning owner of Bailey Communications, a corporate writing consultancy.

Twitter: @LittleVagabonds
Instagram: mylittlevagabonds

Cliff Hsia is a writer, husband, and father, who is determined to live a better than normal life by traveling the world, slowly and purposefully, with his wife and two young daughters. His writing has been featured on MSN, TODAY, The Huffington Post, The Good Men Project, and other publications. He writes about travel, parenting, and lifestyle design.

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  • Sierra

    My husband and I have 2 children and so far, our only out-of-country trip has been to London….&& we loved it!! This is my first time reading your blog and I’m already inspired! We have 2 children and both of us are going to finish up put degrees (my Master’s in Higher Education and his in teaching).

    It works out that these are our desired professions because in both of which, we will be able to live out our nomadic lifestyle & still make money as we go along. Of course it will look a bit different from that of your, but I’m optimistic about making it work when our time comes! We have 2 children (3-1/2 years apart) and we want to whats within out power to provide them with the fulfilling and culturally-enriching lives, while gaining even more life experiences ourselves. Most importantly, we get to do it all together!

    I am loving your story! Keep sharing!

    • Sierra – Thanks for reading and sharing a little bit about yourself. It’s great to hear that you’re making travel a big part of your children’s educations. Wishing you all the best!