It’s never been easier to jump on the internet and book an entire vacation in less time than it takes to brew your morning coffee. While convenient, these trips can feel a bit sterile. From airport transfers to mega resorts to pricey excursions, most travel today is engineered for efficiency and profitability. There’s certainly a place for this type of travel and we have used all of the aforementioned services ourselves. But our most memorable and meaningful travel experiences have come from taking the road less traveled.

Over the years I’ve realized that no two people interpret the world the exact same way. We all view the world around us through a unique lens that is shaped by how we’re wired and by our experiences. The exciting news is that we all have the power to choose these experiences. We get to choose what we read, watch, listen to, and who we interact with. The story of our lives is written by each of these tiny choices.
One of the most powerful ways that my husband, Jeremiah, and I have changed our perspective is through travel. Travel has changed how we see people and other cultures. It’s changed what we value and how we live our lives. Travel has taught us how to deal with change, overcome challenges, and has improved our confidence. And all of these changes came from choosing to take the road less traveled.
Jer and I started traveling by taking the safe and secure route. The first big trip we took together was to get married in Hawaii. I booked a flight, hotel, and airport transfers directly through my local airline. The following year I used a travel agent to book an all-inclusive vacation package, which happened to be our worst trip ever. That challenged me to consider alternatives.
The following year I booked a flight, car, and beach cabana individually. The experience was so amazing that each year we were inspired to be gutsier and step further outside our comfort zone. We began to truly appreciate the moments we discovered a hidden gem after getting lost. We laugh about the crazy stories that came about from befriending the locals. And we’ll never quit searching for the world’s best deserted beach.
Taking the road less traveled has become the way we always travel, but for the purpose of this post, I’m going to zero in on specific place. Join me as we travel 5,500 miles to the beautiful and historic country of Greece. During this trip, Jer and I had the opportunity to take the road less traveled and visit incredible places like Methana, Sifnos, Milos, and Meteora. Through these experiences, we got to know the real Greece, which we will forever hold a special place in our hearts.
5 REASONS TO LOVE THE ROAD LESS TRAVELED
LEARN THE LANGUAGE
When you take the road less traveled, you can’t help but pick up the language. The further you get from the popular tourist attractions, the less likely you are to hear your native tongue. But don’t let this deter you. People will go out of their way to help you whether you speak the same language or not.
I do a pretty great job planning our trips so that we can spend more time enjoying them instead of wasting time trying to figure things out. As part of this trip, we planned to take a road trip to northern Greece. I printed out all of the driving directions and even had a backup copy. What I didn’t consider was the possibility that the road signs would only be written in the Greek alphabet.
So there we were with directions in English that were completely worthless because neither of us could read the Greek alphabet on the road signs. Let’s just say that tension was at an all-time high and we weren’t being very nice to each other. Since I was navigating, I asked Jer to pull over at a World War II Memorial. I spent the next 20 minutes memorizing the alphabet so I could try to piece together what the signs said.
While it wasn’t the most pleasant experience at the time, I look back at it with fondness. Each time we’re forced to communicate in another language it gets easier and we feel more confident. I also learn new patterns and words that help me communicate better in English. Everything about it was a wonderful learning experience … after the fact.
FIND THE BEST FOOD
Food is so much more than nourishment. It’s not one of the five official love languages, but I think it should be. Our rituals around food are social and spiritual. Food is part of our memories. And the best food experiences are usually found in someone’s home, down a dark alley, or in a building that’s unlikely up to fire code.
The most amazing food we’ve tried while traveling was found in these off the beaten path locations. During our last night in Athens, before flying back to the US, we wandered down a dark alley near our hotel and discovered a restaurant called Vassilis. They had the most delicious souvlaki we had in the entire country. It was so good that I sometimes dream of flying back to Greece just for that dish.
Given that flying halfway around the world to eat dinner isn’t in our budget, I learned how to make the dish at home. Then a couple of times each year we’re transported back to that warm summer night in a quiet neighborhood café. A café we would never have discovered had we not wandered down that dark alley that most travel guides would tell you to avoid.
STRETCH YOUR BUDGET
Have you ever noticed that the further you get from the touristy areas, the farther your dollar goes? While the hotels in Athens make you feel at home with American amenities, those amenities come with a price. We used hotel rewards during our visit, but the going rate at our hotel was over $200 per night. Compare that to the mere $60 we spent nightly in Meteora and you could easily save around $2000 on lodging over a two-week trip.
Lodging is just the start. Small town restaurants offer delicious and inexpensive meals made from scratch. If you enjoy sightseeing, you could visit four monasteries in Meteora for the same price as one ticket to the Acropolis. Did I mention the added benefit of smaller crowds?
LEARN THROUGH EXPERIENCE
In Greece, we learned lessons about history, theology, and sociology. While we learned many of these things through formal education, we gained a brand new perspective by experiencing them in real life.
My husband, Jer, is a huge history buff. Even though history isn’t my favorite topic, his stories about Hadrian and the Roman Empire made Athens come alive. All of that old stuff had much more meaning once I understood the stories behind it.
I also enjoyed learning about the Greek Orthodox faith in Meteora. But the thing I enjoy most about travel is cultural immersion. The Greeks are social people and have mastered the art of slowing down and enjoying the little things. It was a big eye-opener and something I desperately needed to get better at.
BUILD CONFIDENCE
Self-confidence is like a muscle that gets stronger the more we use it. And there’s no better way to exercise that muscle than by stepping out of your comfort zone. The more frequently you do things that scare you, the easier it becomes. The more challenges you overcome, the more you believe in your ability to do so.
I started these five lessons with a story about driving so I may as well end with one as well. Now that I think of it, a lot of our best travel stories happen while driving.
Remember how I told you about those worthless directions I came prepared with? It gets worse. After my crash course in the Greek alphabet, we eventually found our way to Delphi. It was fairly well marked being a popular side trip from Athens. However, driving from Delphi to Meteora was another story.
On top of my directions being worthless, we found that most of the roads going back through the mountains weren’t marked. At one point Jer said, “I feel like we’ve driven through here already.” Panicked, we pulled over as the sun was setting and consulted a map. I’m not sure how we did it but we finally made it down the mountain and to the road to Meteora. It was dark, we hadn’t eaten all day, and we still had a few hours ahead of us. We survived on licorice I had in my bag from the flight to Greece.
It was late when we arrived at our hotel. Everything was shut down and we had to ring the bell to get the owner to let us in. Thankfully the Greeks like to eat late and there was one restaurant open down the street so we could eat our first meal of the day at 11 pm.
That’s the thing about travel. You learn that everything always works out. How would life be different if you approached your daily life with this attitude?
With that, I’d like to extend a little challenge to you. The next time you plan a trip, commit to trying something new. Step out of your comfort zone and take the road less traveled. Start with baby steps like renting a car for one day. Or commit to trying a new food each day. You will never regret the experiences the road less traveled offers you.
Do you enjoy the road less traveled? What have you learned on your journey?
PIN FOR LATER



Editor’s Note: This post was originally published in March of 2016. It has been completely revamped for accuracy, comprehensiveness, and readability. Please enjoy and feel free to share this newly revised content.
Holly you and your husband are truly adventurous and very courageous! That’s definitely not something I can see Alex and me doing! I am Greek and my dad took us to Greece when I was 20 – it was an incredible trip so I especially loved your pictures and they brought me right back to that time! While I speak the language (not as well as when I was a kid) and can read a little – I still would find maneuvering around challenging. You guys are an inspiration!
Thank you, Ann. We have trained ourselves to be adventurous by taking a new step out of our comfort zone each time. It’s also nice that we push and support each other.
Greece is such a beautiful country and the people are so warm and generous. You must have had a blast growing up in that culture.
Holly, you and Jer are an inspiration. The trip sounds absolutely life changing, and I know that going off the beaten path made everything far more spectacular. Who wants all the amenities and the comforts of home when you’re traveling away from home anyway? Immersion, experience, that’s where you find the true gold. I happen to love the road less traveled. Thanks for sharing your journey.
Holly,
We are planning a trip to Machu Picchu with our kids in 2018. This post really drives home some of the reasons we aren’t going to some of the more traveled places. Hiking the Inca Trail seems so much more, us than a cruise or another typical trip.
Thanks.
Thank you for the comment, Robert. Travel is always life changing. We need to figure out how to do more of it.
I love your point about the comforts of home. Many of the places we have traveled, amenities were not an option. It has changed what we see as acceptable and necessary. It has also changed what we consider a necessary amount of living space. Learning to adapt to new environments has been a blessing indeed.
Always love to hear from others who take the road less traveled. What has been your most memorable experience?
Hey Holly – I love your generous perspective on your trip to Greece. I too was overwhelmed to realize I couldn’t navigate because I didn’t know the Greek alphabet. Fortunately I had my friend who knew Russian and could pinch hit for us. Aside from the fact that the internet was brand new when I went, how did we not know that??
I love this “Self-confidence is like a muscle that gets stronger the more we exercise it. There is no better way to improve your confidence than by stepping out of your comfort zone.” I think you are so right! Takes courage to commit and then follow through, for sure!! 🙂
Erin, thank you so much for the kind words.
I’m with you – “how did we not know that?” Not only could I not read the signs, they made no sense. Rather than Hwy 23, it was the road to Delphi. It took me a while to make sense of that. Before the trip, I diligently took planned the route and printed directions, but with no road signs, they were useless. Fun times!
Wow John, that sounds AMAZING! That’s a place I’ve always wanted to visit.
You know, I’ve never been on a cruise. There’s something to be said about a nice relaxing vacation, but I always feel like I missed something.
Sure thing Holly! Well, here’s one off the top of my head. I remember we were driving through the Adirondacks mountain range in New York. We were coming from Ohio. I have Siri (gps) on much of the time, but I tend to do the opposite of where she’s guiding just to take off roads.
After staying over at Lake Placid, we decided to make our trek toward Vermont. Just taking wherever the long and windy road lead us. It was beautiful.
Next thing you know it we ended up at this giant lake. I decided to give Siri a shot at that point, and she pointed for us to drive right through the lake. Did some lookups and realized we were pulled up to a ferry doc at Lake Champlain.
Lo’ and behold we found ourselves waiting for a ferry. We drove onboard, and the boat took us and the Pathfinder across this breathtaking lake at sunset and right into Burlington, Vermont. We walked around the boat during the ride, and just enjoyed the beautiful white sails in the distant and the setting sun.
Oh Robert, that sounds incredible. You’re making me rethink a trip we’re planning. My husband always wants to drive so we can bring our bikes. If it’s over 6 hours away, I tend to say NO WAY! That’s a lot of time in the car, but sometimes that’s where the magic happens. Thanks for sharing.