The difference between travel that transforms you and just another vacation with photographs and fond memories isn’t chance.
I don’t know about you, but I’ve experienced both. Pictures and laughter are great, but not what really inspires me to travel.
Connection with myself, others and the world.
A deeper sense of meaning that goes beyond sightseeing and dives straight into the heart.
After many trips, some transformative and some not, I’ve learned the difference between the two is not happenstance.
Although we definitely can’t control what happens on a trip — that would defeat the whole purpose! — we can most definitely, purposefully, set ourselves up for the revelations we desire, and snap the Insta-worthy pictures, too!
In this article, I’ll share three of my craziest life lessons from travel and four simple, but powerful tips sure to turn your next trip into travel that transforms you at the deepest level.
Best of all, you can use these tips whether you’re traveling across the world, or simply diving deep within your soul right here at home.
Miami, circa January 2005.
It was raining in Philadelphia, and I was sad.
About to graduate college, but feeling very lost and lonely, still healing from the deaths of my father and sister nearly 10 years earlier. Drowning my feelings in alcohol and basing my worth on the number of party invites I received.
All I dreamed of was moving to Hawaii to work on a farm after graduation, even though part of me feared I wouldn’t follow through. It seemed like other people always said they’d do adventurous things with me, but then backed out.
I had this feeling that if I acquiesced to my fears and stayed in Philly after graduation, I’d wake up years later furious at myself for not having the adventures I wanted.
Torn between the desire for adventure and panic that a gap in my resume would ruin my life, I waited out the remaining months of college, hoping for universal guidance, which wouldn’t come until later.
But on that January night, I felt stuck. Sad. Done.
So I left. Took a little nap and left late that night, driving 18 hours down I-95 straight to South Beach Miami.
I arrived in the humid January air and, after checking into my hostel, headed straight to the bar for a cold beer.
It was there I struck up a conversation with a nice blonde woman, who moved to South Beach a few years earlier.
She told me something I’ll never forget: If you wait for other people, you’ll be waiting your whole life.
That sentence stuck with me, and ever since, I’ve never waited for anyone to do anything.
Consequently I often do things alone, but it’s better than never doing them at all.
Ah, the beauty of travel that transforms you.
Maui, circa 2005-6
I landed on Maui late summer 2005 after finishing my last classes and working a temp job for an insurance company that ironically had to hire people to go out of business.
My days were spent taking files and adding the information inside to a database while listening to music and flirting with a boy hired to move boxes of said files around.
It was my first taste of the office life. Even though my sultry little romance livened things up, I decided right then and there I’d never spend my precious days locked up behind glittering skyscraper windows.
The offices looked so beautiful, but they felt like cages. And I longed to be free.
Sadly, the farm turned out to be a fruit stand sham. We’d unbox Dole pineapples each morning, rip off the tags and place them on the shelf of the roadside crepe and smoothie stand.
The farm’s actual pineapple groves were not functioning. Eventually I found a job at a Greek restaurant and rented a room in a house of boarders.
Maui is known as the planet’s heart chakra.
Each of the islands has an incredible, healing energy and on Maui, mana, what Hawaiians call life force energy, feels strong.
For my entire life, ever since my dad and sister died, I’d repressed my emotions.
My mom and I never really spoke about what happened, but it was then on the island, that I started a conversation and we cried together for the first time, 10 years later and 5,000 miles apart.
Maui healed me, but still‚ whenever someone asked about my family, I never knew what to say.
Bypassing the question felt like dishonoring their memories. But telling the truth always created an awkward pause in conversation, and I never liked navigating that.
As the mana worked its magic, things shifted.
I was super sassy in those days. If a guy I wasn’t interested in refused to leave me alone at a bar, I’d make up fake personalities and mess with him.
I’ll never forget one night, a guy making conversation asked if I had any siblings.
In that moment, that night, for once in my life, I told the truth.
“I had a sister,” I said, looking him straight in the eye. “She’s dead.”
Costa Rica, March 2014
By this time I was living in Arizona, hating it. I’d quit my marketing job to freelance write the year before, but felt boxed into a life I hadn’t intentionally created.
I needed a change, but wasn’t sure how to create it.
After a big month in my business, I decided to take a little trip to Costa Rica, do yoga and soak in the sunshine.
The entire trip, I kept looking for that message, a great wisdom to create a breakthrough in my life.
I’d arrived with a strained hamstring, pasty skin and tired heart, and left glowing, hamstring healed, and strong from afternoons spent surfing.
But still no revelation.
It didn’t come until the plane ride home, when a voice within said —
“For your life to change, you have to change.”
And now here we are!
The heart of travel that transforms you
Some people travel to see museums and do all the things.
That’s never been me. I don’t travel to do, but to feel.
One of my core values is spaciousness. I like traveling slow, both in time and pace. Walking around, seeing, tasting and touching the space. Wandering off the well-traveled trail.
I usually travel alone, and when I was younger and drank a lot, enjoyed hitting the bars, which was always a great place to meet people.
Now, I don’t drink, and for some reason it feels harder now that I’m older to connect with others on the road. Because of that, I haven’t found my new pace in traveling yet.
More recent trips have felt sadly boring (I know, first-world problems!) because I am an introvert and end up walking around by myself all day, hardly talking to anyone.
I haven’t gone on retreats because I hate having a packed schedule, and even more detest the idea of having things scheduled for me. Fuck no.
But the idea of using travel as a transformative spiritual experience has always appealed to me.
When I was younger, while my stated dream of ‘doing crazy things’ seemed about the doing, underneath it was about experiencing things unique to a place, and in doing so, feeling the soul of that place.
Farming in Hawaii wasn’t about a fruit stand, but about connecting with the Earth and seeing how different people lived.
Last year, I planned, but never went, on an olive harvest retreat, which was about more than olives, but travel that transforms you.
The deeper desire was to learn from people who have been harvesting lands for generations, to see what the olives mean to these people, and how their relationship with the land influences who they are and how they live.
I haven’t fully connected to HOW to experience these things (I don’t want to rely on retreats), and not having the skills to bring the stories to life terrifies me.
I’m not one of those people who can plop down in a foreign land, make instant friends, and jettison off on new adventures.
Maybe when I was younger…
But I’m not that person anymore.
Or maybe she’s asleep and I’ve just lost connection to her.
Either way, I believe travel always has the potential to give us what we’re looking for.
To awaken within us things that need to be awakened.
To connect us with ourselves, with the Earth and with other people.
To see that no matter how different we appear to be, we are, at the core, all the same.
And with that, here are 4 tips for spiritual travel that transforms you:
1. Ask the universe for guidance on where to go.
I believe different places unlock different lessons within us. Each place has a different energy, and the mixture of that energy with your soul’s energy will create specific shifts for you.
I also believe places call us when they want us.
Before moving to Maui, I asked the universe for guidance and saw three Hawaiian license places in Philadelphia, days apart. Never underestimate the universe’s ability to guide you.
Also never underestimate the power of your desire. If you receive a sign to go one place, but have the strong desire to visit another, honor your desires.
Sometimes signs show up to help us get clear on what we actually want, and your desires are always guiding you to the truest path for you.
2. Set a divine intention.
You definitely won’t know the exact lessons that you’ll learn, or the precise insights that’ll unfold. If you did, there’d be no point in going!
But it can be really powerful to set the intention for how you want to shift, or clarify what you’re looking for.
Wanting to find yourself or receive direction on your life’s path are great intentions. So is wanting to release a certain pain.
Maybe you want to connect with a part of your history, or your family’s.
Maybe you just want to have fun.
Part of the reason I’m headed to Italy (even though I planned to return to Bali) is because I’ve been so deep in spirituality that I’ve lost my connection to savoring life.
I feel like Italians know how to live, and that’s what I’m most looking forward to on my trip next month.
3. Let how you want to feel guide trip planning.
I like to feel spacious, so for this trip, I’m spending an entire day in Florence before heading to the retreat center, and spending the night there again before flying out the last afternoon.
I don’t like to wake up early, and I don’t want to have crazy long layovers, and those desires influence my arrangements.
Travel inevitably has uncomfortable elements — why make it harder on ourselves? Even if it costs a little more, it’s worth it.
Specifically for the transformation element, I also knew that I didn’t want to spend the entire time alone, so I found a retreat without a lot of structure that would balance my desire for connection with my desire for freedom.
Bookending a few days on either side gives me the space to do my own thing, too. My intention is to be honest about who I am (an independent loner who enjoys talking to strangers), and create a trip honoring that.
4. Connect to any deeper meaning.
My sister spent a semester abroad in Italy, so I am excited to walk the streets of Florence knowing that in some way, I’m getting to know her in a new way even though she’s been gone all these years.
It’s not the prime motivation for my trip, but connecting to any deeper longings can help us make sure we’re getting what we most desire from the experience, which is often a sense of meaning, not not a sense of seeing 500 museums.
Museums are fine, but we don’t actually travel to see things.
We travel to feel things.
And that’s the most important thing with planning travel that transforms you.
Also — right now I’m reading The Art of Pilgrimage, The Seeker’s Guide to Making Travel Sacred, so I’ll have plenty more about the art of spiritual travel to share! (Full disclosure, that’s an affiliate link. If you purchase, I receive a small commission at no cost to you. Thanks for the support!)
Now I’d love to hear from you.
Share in the comments below — What is your most transformative travel memory? What is your favorite trip? Or what are your trips for travel that transforms you?
I love hearing from you, so please do share.
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All the love,