Discovering  Transformational Travel 

The mountains of Costa Rica are transformational

The horizon above the jungle in central Costa Rica.

I’ve been blessed to have traveled for many years both in my personal and in my professional life. And only after many years and many miles have I come to understand how transformational travel can be.

Some of my favorite travel was and is, the simplest.

Easy, casual trips on my own time.

Like to my hometown on gorgeous Lake Winnipesaukee in New Hampshire, or the rough and rocky coast of Maine, sleepy Anna Maria Island on the west coast of Florida, or a simple overnight staycation to a new city in Florida.

Relax, recharge, reflect. That’s what it’s all about.

And in my professional life I’ve been fortunate to travel extensively in a fashion I honestly could never afford. Not then, not now.

To some pretty amazing places.

We’re not talking about the occasional sales convention in Vegas (no disrespect).

We’re talking mind blowing, Insta-worthy experiences.

Waking up to the big surf outside my window on the Big Island, party at the foot of the pyramids, exploring the Summer Palace in Russia kind of travel.

Travel to the destinations people most want to visit –  ‘cuz that was my job.

Vetting out the resorts and experiences these destinations had to offer.

Yep, that’s really a job and I had it. (I know- sorry, not sorry)

It’s About the Moments

Despite the optics, I didn’t “get it” until I was well into my 50’s.

I didn’t really get that these destinations were more than a check box on my bucket list, bragging rights back home or the perfect photo opp.

Looking back, I’ve a tiny bit of sadness for the squandered opportunities to be more than the ugly American, to get out from behind my camera and just be.

To honestly connect with the destinations and the people that are those destinations.

Don’t get me wrong. That was the best gig ever.

But I now know there was so much that went unseen, unfelt.

How untested I remained despite all the miles.

The infinity pool at Alta Gracia at sunset

Infinity Pool at Hacienda AltaGracia in the mountains of Costa Rica   (Cynthia Howland Image)

“We travel, initially, to lose ourselves; and we travel, next, to find ourselves. ~ Pico Iyer”


And with each passing year, I realize how bits of my travel have changed for me.

Yes, it’s still a thrill to stay in a level of luxury that far exceeds my budget.

Yes, it is amazing to share in some of those experiences with my friends, or just reflect on them on the plane ride home.

But somewhere along the line, I stopped coming home with travelogue, picture perfect memories, a SIM card full of images and the obligatory chatskis, and tee shirt.

At some point, my experience was no longer passive.

I was no longer an observer, no longer the “accidental tourist,” but rather I found myself smack in the middle of the life.

A life different and foreign, and yet all so familiar.

That’s really it, isn’t it.

Those random and unanticipated points of connection and recognition in the midst of the unfamiliar and the unknown.

The familiarity of the human fabric in the midst of the diversity and division and the wonder of the previously unseen.

That unexpected delight of finding yourself Immersed, engaged, (all those words that get used) in moments that touch us profoundly and then never really leave, that take up residence in our suitcase never need be unpacked.

That is the real discovery.

That is the wonder.


 “The real voyage of discovery consists not in seeking new landscapes, but in having new eyes” – Marcel Proust.

People bring Alta Gracia to life.

Alta Gracia – It’s the people that bring it to life. (Cynthia Howland Image)

It’s the People, Dummy.

Yep, it’s about the moments and those who inhabit those moments with us.

Moments sometimes seemingly small and insignificant at the time.

Idle chatter with a storekeeper in the leather shop  who perks up at my American accent and immediately asks “You from New York?”

Sitting quietly on a patio in the early morning watching the fog clearing from the mountains of Costa Rica in the distance. The peaceful trance from gazing across the verdant grounds that slope down to the narrow strip of road, broken only when the staff starts trickling in to work in the early dawn, some by bicycle, some bidding long and reluctant goodbyes to their young love in a beat up car before they start a day full of promise.

Those lovely moments of watching the resort come alive and the people who wake it up.

And that’s it.

It’s the people, dummy.

It’s their often simple but bursting pride about  the service they offer and the property they serve.

Their enthusiasm to share the specialness of their home, their curiosity about the states.

The beautiful, brave and halting use of the English language and their joy as they share what it means to work there, how coveted that job is, their families and their lives.

Is it Age or is it Circumstance?

I’m not exactly sure when this changed for me.

But I do have a hunch about the catalyst.

There were a couple years following the “implosion” of my life when I didn’t do much traveling except that one healing trip to visit friends in Italy, and a summer of licking my wounds at the lake.

I didn’t do much at all to be truthful.

And of course, there’s the perspective of age too.

I guess I’ll never be able to sort out how much I was changed by age and how much I was just changed by “stuff.”

It morphed together at one point and I suspect I’ll never know.

Curacao welcomes visitors to Willemstad

Willemstad in Curacao, with open Queen Emma bridge

When I became a participant in my travels, a participant in my life really, I allowed myself to be open, to be curious, and to be unafraid.

And then the magic began to happen.

I began to be changed by the moments.

They became a permanent and organic living part of my life, and they left their imprint on me.

Traveling at a most vulnerable time, I was afraid.

I was afraid of everything back then.

It seemed life had betrayed me, fooled me.

And then finally I surrendered. I was willing to change my way of viewing the world.

Why not?

And that’s when my wanderings began to matter.

I had begun to explore.

That’s when I started to notice I came home changed and often empowered.

I brought home more than I left.

I was transformed.

And then I found out it’s a thing.

Yes, transformational travel is a thing.

“ The journey changes you; it should change you. It leaves marks on our memory, on your consciousness, on  your heart and on your body. You take something with you, and hopefully you leave something behind.” Anthony Bourdain


Mountains in Mexico are made for relfection

The Mountains of Mexico – Meant for reflection. (Cynthia Howland Image)

What is Transformational Travel?

Remember experiential travel? The call a few years back for “authentic experiences,” connecting with locals, experiencing the destination up close and personal.

Well, it turns out experiential travel is ‘so yesterday.’

One step beyond experiential travel is transformational travel.

The big difference?

It calls for a more mindful experience that leaves a long lasting effect on us.

It changes us by leaving us with a new perspective, a new awareness, a new world view and it leaves its mark on us forever.

The Transformational Travel Council, newly formed in 2016 is committed to launching transformational travel (TT) as “the next great movement in travel.”

Their mantras: “Intention, Engagement, Mindfulness, Reflection and Action. “

Their mission is sharing stories to help travelers create their own life-changing travel experiences, and helping the travel trade design those experiences.

Sometimes the moments are big, and you know it when they’re happening.

Sometimes those transformational  moments are big, and you know it when it’s happening.

I traveled to San Miguel de Allende in Mexico – a beautiful colonial town in the mountains of Mexico for a writing retreat with two writer friends. Visually lovely, historically important and architecturally and culturally rich.

Knowing my corporate persona was irretrievable and  untenable for oh, so many reasons, I was in search of some sort of clue to the path forward.

The very cave you are afraid to enter turns out to be the source of what you are looking for. ~ Joseph Campbell

Teotihuacan Pyramid- A place for transformation

Teotihuacan Pyramid, The Pyramid of the Sun. It’s bigger than it looks! (Cynthia Howland Image) 

The Transformation Was in the Side Trip

I’m not going to lie, the conference was inspiring and important, and hearing Gloria Steinem up close is not a waste of time!

But the transformation in Mexico was the side trip I took by happenstance before the retreat. I had been connected by a casual acquaintance with a couple who were anxious to create a spiritual retreat. Apparently they thought my background in resorts and interest in the spiritual could be useful. (Not really )

I arrived two days early to meet them and take a trip into the mountains on what would be their proposed itinerary for their guests. So traveling into the mountains of Mexico with two complete strangers? Probably not advisable.

After lots of traffic through Mexico City in order to avoid the dangers of traveling around the city we reached Teotihuacan Pyramid- the Pyramid of the Sun.

Oh my gosh!

There was a hush across the grounds at the foot of the pyramid that made every stone seem sacred.

Carried by a whisper of a breeze, It was one long enveloping and embracing hug.

I felt safe and in the midst of something important, yet something familiar.

The pyramid was imposing and much larger than it looked in the pictures.

No, it was flippin’ huge!

People of all ages ascended it, undaunted by the height or the skinny and irregular steps, covering it in the distance like ants.

Now I’ve had a fear of heights since I was a child, replete with a recurring nightmare that followed me well into adulthood. (I climb a ladder to get up on a roof, and I can’t get down cuz I’m afraid to get back on the ladder.) I’ve had it dozens, maybe hundreds of times over the year.

I easily climbed the broad steps of the first level of the pyramid, stopped and looked down.

Whoa! Nope. Couldn’t do it. I started to head back down.

My “friends,” saw my terror and they stopped me. Quietly. Calmly.

They took my hands in theirs and said “Let’s make this fear stop today.  Let it go now.” I know. Sounds a little woo woo right?

We stood like that for a minute or so. I have no idea why I believed them but I knew I could do this. And off I went up the skinny and uneven stairs.

I held on to the safety rope for dear life, and just put one foot in front of the other, without looking down, without stopping.  Almost 20 stories.

At the top, I felt exhilarated.

And then I looked down. We were really high up, and the wind was blowing.

It was exciting, empowering and frightening at the same time.

I hung tentatively in the center of the pyramid while others climbed over the sides, took selfies and otherwise made themselves comfortable.

I’d done it. How was this possible?

It hurt to think about how much I had missed in life by letting myself just opt out.

Of the hard stuff I should have done.

Peer pressure was nothing to me, I made no apologies. So opting out came easily to me.

I made a decision that moment to stop sitting it out.

Infinity pool at Alta Gracia - A place to transform

Infinity Pool in the Mountains. It seemed prophetic!  (Cynthia Howland Image)

That evening, at my hotel sitting right at the base of the mountain, I sat on my patio long into the night, proud, and knowing that I would be ok.

When I returned home, I recalled beautiful and charming San Miguel and its lovely artsy community.

But my moment, my lesson was the achievement, euphoria and excitement of standing on the top of that pyramid.

My lesson was pushing through, one foot after the other.

It was those beautiful strangers who took my hands and willed me to chase down my fears.

Today, I’m still in contact with those lovely, spiritual people who knew exactly how to help me. And that unexpected healing trip into that quiet sacred space that  left its mark on me forever.

I soon had the opportunity to test myself.

Emboldened by summit of the pyramid, I was again faced with my fear of heights.

I was on a writing assignment at a gorgeous mountain top resort in Costa Rica. Their signature attraction was an ultra-light flight over the mountains and out to the sea. An ultra-light is an open, (yes, open!) single engine, (yes, just one) 2 man aircraft.

I reminded myself I had left my fear of heights on the pyramid.

And I did it. Without hesitation, without self-doubt. Yes, I was scared but willing to trade it for the pay off.

The power of flying in the open air over the mountains and out to the sea was amazing. And I think about that, and the top of that pyramid when I’m faced with my crazy fears.

Ultralight flight- Transformative Travel

Ultralight flight into the clouds. (Cynthia Howland Image)

Sometimes the moments are small.

Transformation comes in big and small ways.

In Curacao the resort I was writing about had arranged for the driver to show me the island. We drove hours to have a simple lunch at a roadside cantina, where he (and I, by extension) were treated like family as the cook came out with his luncheon recommendation, and my companion pulled up a chair and played a couple songs on his beat up guitar. We drove for several hours, my escort with his eye on his watch as we arrived at his special spot on a cliff. He painstakingly positioned me against the backdrop of the setting sun so it created a perfect heart shaped frame around me.

He chatted the entire way pointing out livestock, wild life, and in short, sharing his life.

The images I brought home of the island and the resort are stunning, but the memories of Miguel and his friends are indelible.

Lake Winnipesaukee- Going home is transformative.

Home at the Lake – It doesn’t get any better. (Cynthia Howland Image)

Exit 20 – Bienvenue au New Hampshire.

Transformation doesn’t require exotic locations, or vast distances of travel.

Each time I go home, I’m 10 years old again exploring in the woods to the sound of the rustling spring waters

I’m swimming in the crystal lake waters or driving my blue Mustang.

I’m a young woman getting married on the hill with my parents watching.

Each time I see that Exit 20 sign, my heart breaks just a little bit again, for all of that, for who I was,  and for all of us.

All for those shades of me that grow more distant with every sunset.

And what do I know from all of these miles?

That people and places change us. And when travel manages to transform us, it’s magic.

It will always be about the people. How we let them in, or how we don’t.

It will always be about the moments. How they help define us and the mark they leave on us.

It will always be about the places and the memories that are tied to them.

And by the way, this might just happen right in your own back yard if you open up to it.

I’d love to hear from you. What travel experiences have left their mark on you?

Let me know in  your comments below in the white box.

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For more on new ways of being in the world, take a look at Get You Mojo Back! The Joy of New Beginnings

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Some of the links in this article are "affiliate links", a link with a special tracking code. This means if you click on an affiliate link and purchase the item, we will receive an affiliate commission. The price of the item is the same whether it is an affiliate link or not. Regardless, we only recommend products or services we believe will add value to our readers. By using the affiliate links, you are helping support our Website, and we genuinely appreciate your support.