An Interview with Greg and Rachel Denning

Keynote Speaker for Family Adventure Summit 2017

An Interview with Greg and Rachel Denning

Driven by a vision of living more than an ‘okay’ life, in 2007 the Denning family set out on a journey that would change their lives forever. Their decision was based on a burning desire to live deliberately —  to consciously design their family lifestyle to include the things that really mattered to them — travel, adventure, language, culture, fun, education and making a positive impact on the world.

Find out more about their family’s journey at

Tell us a bit about your family and what kind of traveling you have done.

Hi! We’re the Dennings, a long-term, slow-traveling family. There’s nine of us — seven kids — and we’ve traveled to over 30 countries on 5 continents over the past 10 years.

How old were your children when you first started your traveling lifestyle?

When we first started traveling in 2007, Greg and Rachel (mom and dad) had four children, all under the age of four (ages 3 months, 18 months, 2 years and 3 ½ years old).

What was the catalyst that made you decide to live life differently and travel the world with your family?

Until I had four children, I never owned a passport or left the U.S., except for day trips to Tijuana or Niagara Falls. My husband had lived in Peru for 2 years, and later went back for a 3 week humanitarian trip after our third child was born. I was intrigued, but at that time I thought “There’s no way you could take kids to Peru. It would be too… [dirty, dangerous, etc.]”

But the idea of having an ‘international experience’ kept growing on me. My husband spoke Spanish and we wanted our children to learn another language. This idea continued to grow in the back of our minds, but we also believed that in order to travel, you had to have lots of money.

So we worked on making more money. We also looked for ways to earn income that was ‘passive’ so we could leave the United States. Real estate investing, rental properties, and stock options trading were all things we started doing, with great success (at first). My husband quit his ‘corporate’ teaching job (which he actually loved, but which would never give us the option to live abroad), and we began moving toward that ‘someday’ when we would be rich enough to travel with our kids, or maybe after they were grown.

Then Greg surprised me (Rachel) with a spontaneous second honeymoon while I was expecting our fourth child.. We flew to Cancun where we did the typical tourist stuff. But one afternoon we left the tourist track and had a local experience at a church. I sat surrounded by Mexican people, singing, talking and laughing, and while I didn’t understand the language, I had a sudden realization that these were people, just like me, who married, loved, laughed and worried about their children. Despite barriers of language and culture, they were as human as I was. This was an experience I wanted to have again, and that I wanted my children to have. Most of all, I wanted to help them grow up with an expanded reality, and ‘broad, wholesome, charitable views of men and things.’

I told Greg we should move abroad and he immediately agreed. After that trip we started making preparations, and once our fourth child was three months old, we packed up and started driving to Costa Rica where we planned to live.

How have you chosen to educate your children while traveling? What are your educational philosophies?

Even before we started traveling we’d planned on homeschooling our kids, but once we began traveling we termed it ‘worldschooling’ instead, but even that definition has morphed over the years as we learn and grown. Sometimes it’s looked more like ‘unschooling’ or natural learning, especially as the kids were younger, but it’s become more structured as they age and crave more challenge. Ultimately, our educational philosophy includes four main pillars:

  1. Personal Leadership and Development — helping them to become their best selves and to develop positive habits and world views.
  2. Classics (Liberal Arts) — exposure to the enduring truths and principles of the ages, from all cultures. Stories, fables, myths, spiritual literature, music, art, ideas, and helping them take part in the ‘Great Conversation’.
  3. Mentors — children learn from the example of others, so we inspire them to become their best and pursue an education through example, and by introducing them to others (peers and adults) who encourage them on this path
  4. Adventures and Experiences — powerful things happen when you experience something firsthand. It makes what you learn and feel ‘stick’ for a lifetime. It changes your paradigm of the world. It transforms your outlook on life.

Tell us one of your best worldschooling moments.

One week in January (2017) we visited the city of Marseille, France. We’d been too busy to do our research beforehand, so we weren’t sure what to see or do. The little ones were bored and wanted to go ‘home’. The baby was fussy. Mom and dad couldn’t agree on anything. There was a bit of contention.

But as we crossed the street toward the tourism office, an old woman wobbled up toward us, cup in one hand, cane in the other, supporting herself as she tried to ‘walk’, if you could call it that. Her feet were wrapped up in a ball shape and looked like they were bent at 90 degree angles at the ankle. Every limb shook uncontrollably. Her head was covered by a scarf and her face was not visible. Suddenly nothing else mattered. Here was a human being in real need. I had no coins or cash, but we knew we had to give her something. So I led her to sit down and held her hand, which never stopped shaking, while my husband ran to the ATM. She immediately began to cry, and so did I, as I asked if she spoke French or English. She shook her head, but I did understand that she was from Bosnia. She pointed to my children and signed to me that she had four children back in Bosnia. I wondered where they were and why she was here alone. Was she a refugee?

There wasn’t much more that we could do, once my husband returned with some money to give her. We tried to sign to see if we could take her to get food, or help her cross the street. I wondered where she lived and wished we could take her home. But I knew that as sad as her condition was, she somehow managed to survive each day and would continue to do so. It kept her alive. While we looked in the tourism office a couple of my children went back to sit next to her, and my oldest daughter (14) articulated how all the things we’d been complaining about, and all the things we thought were so ‘hard’ suddenly paled in comparison to this woman’s daily struggle.his is what I love about

This is what I love about worldschooling– the unplanned experiences that teach compelling lessons in compassion and comprehension. That one experience taught my children more than hours of philosophy or lectures in a classroom.

What is one thing you know now that you wish you had known before you started out on your traveling lifestyle?

Looking back at when we first started traveling, I almost have to laugh at ourselves. We were so naive, fearful, excitable and ignorant. Driving from the U.S. to Costa Rica, we didn’t even know if there was a road that went the whole way, or if we would be able to buy diapers. We only ate at American fast food chains and stayed in the tourist destinations at all-inclusive hotels. Most of these decisions were based on fear of the bad things that would happen to us in a ‘dangerous’ country. We also believed that ‘living the dream’ would make life a non-stop vacation.

I wish I had known before we started out that most people are good and would rather help than hurt; that a never-ending vacation is actually hell; and that traveling with your family won’t solve your problems, instead it often magnifies them. But travel can help you grow, and as you become bigger and more capable, you’re better able to solve your own challenges.

How do you find community on the road?

We are such a large family that we are a traveling community. Most of my kids are good friends. But we also love connecting with other families whenever we can. We reunite around the world with friends we’ve made before, and stay connected on social media to take advantage of possible meetups as we travel. We also like to stay connected via Facebook and video chats with family and friends.

How do you finance your travels?

Learning how to finance our travels on a long-term, sustainable basis has been one of our biggest challenges. We’ve tried everything we could think of to earn money before, after and during our travels in order to pay for them — blogging, affiliate sales, selling belongings (including my wedding ring), tax refunds, insurance settlements, freelance work, non-profit employment, etc.

As the online world continues to expand, location independent income becomes easier to achieve. Our income source for the past few years has come from my husband using his God given talents — teaching and connecting with youth — via online classes and mentoring sessions, as well as leading adventure and international trips for youth and families.

What is your favorite country so far? Why?

We all really loved Morocco — the colors, the food, the Muslim people, the shopping and artisanry. It’s a place of contrast and culture, teeming with life and energy.

What are some of the difficulties you have encountered in traveling and how have you overcome them?

Traveling long-term with a family is difficult because you’re not only dealing with the normal challenges of life — grocery shopping; meal prep; cleaning; cooking; laundry; homeschool; work schedule; sibling squabbles; adolescent emotions — you’re adding to it travel and logistical planning; regular packing and unpacking; continually new (and sometimes formidable) environments

I don’t know if you ever ‘overcome’ these challenges, you just learn to deal with them, to find solutions. Sometimes I feel our travel lifestyle is one giant puzzle… you’re constantly solving the next problem of visa or passport expirations, where to stay, where to grocery shop, translating languages (on the dishwasher or the grocery shelf), and converting currencies, not to mention dealing with inevitable hiccups and obstacles (like accommodations that fall through or internet that doesn’t work, when your income is internet dependent!)

I like to think that all this problem solving is making me smarter.

Tell us one thing that you have learned about yourself, your family, or the world through travel.

Traveling long-term; dealing with inevitable challenges; being uncomfortable because of language barriers or cultural clashes; meeting people that are just like me, and at the same time, nothing like me at all; it has taught me more than I can express.

Who I am today is a result of ten years of travel experiences. While many people have the same experiences year after year for decades, I feel I’ve lived a thousand lives, and that life only really began after we started traveling. Before that we merely existed. One year of travel experiences seems like ten years of life because so much takes place in a short span of time.

My outlook on life and my place in it; my compassion for humanity regardless of race or religion; my empathy for others and the challenges they face; my belief in myself to overcome obstacles and find solutions; they are all a result of our experiences traveling to and immersing in cultures and languages and places that are different from each other. Diversity is the teacher, and travel is the classroom.

What are your future travel plans?

2017 started off with a grand tour of Europe — Paris, French Pyrenees, Andorra, Barcelona, Southern France, Monaco, Pisa, Florence, Naples, Sicily, Rome, Venice, Slovenia, Croatia, Hungary, Austria, Czech Republic and Germany — before heading to Guatemala for two months. Then we’ll visit the United States and Canada (for backpacking trips, youth camps, and the Family Adventure Summit). Greg will be leading a youth trip to Nepal/Everest Base Camp in September (as well as a WWII European Youth Tour in March). Greg and Rachel hope to travel to Cuba and Patagonia in October and December.

What aspect of the Family Adventure Summit are you most excited about?

We’re super excited to meet up with other families — some whom we’ve ‘known’ online for years but never actually met in person, as well as to meet and make brand new friends.