How An Unplanned Trip Reconnected Me With My Past

How An Unplanned Trip Reconnected Me With My Past


I booked the trip two days before I left. No itinerary, no plan, just a hotel reservation and a feeling, to go. I boarded a JetBlue flight to Santo Domingo and landed almost at midnight. Outside, my car service was already waiting. The driver took my bag, opened the door, and then reached into a cooler and handed me a cold Presidente. I hadn’t even left the airport parking lot, and I already knew: this was not going to be an ordinary trip.


What unfolded over the next several days turned into four unplanned chapters. I can describe it now as Foundation, Fun, Food, and Family, and somewhere between the four, an unexpected homecoming.


Foundation


I started in Santo Domingo’s Zona Colonial, where Christopher Columbus arrived with his caravan on his first voyage, with nothing but faith in the unseen. This is the first European settlement in the Americas — the first church, the first hospital, the first road, the first university, all rooted in these same cobblestone streets.
I wandered without a schedule, ducking into museums and art galleries, browsing little shops, and lingering over dinner in courtyards that felt like they’d been waiting for me. What was once in ruins and unsafe has been revitalized into one of the most beautiful walkable districts in the entire Caribbean. For the first time, and to my delight, I felt safe to wander alone. Standing in a place built on faith in what could not yet be seen, I didn’t realize it yet, but my own homecoming had already quietly begun.


Fun


After a couple of days under the Caribbean sun, I needed to escape the heat, so I headed for the middle of the island — what people call the Alps of the Caribbean. I checked into a hotel in Jarabacoa, a mountain town made for people who love four-wheeling, hiking, and whitewater rafting. The temperatures sat in the 70s during the day and cooler at night. I toured four waterfalls and swam in water so clear and cold it felt like a reset button, in the same spot where Jurassic Park was filmed.


I hired the same driver, Alberto, to take me up the mountain to Constanza the next day, and invited a couple I’d met on the waterfalls tour who were visiting from Washington, D.C. to join me. I had visited Constanza once before, back in 2015, and thought I’d found heaven then. Picture Tuscany in the clouds. It’s the Dominican Republic’s agricultural heartland, and as we climbed, the lush, tropical peaks and valleys took my breath away. We visited a couple of different farms, picked strawberries and flowers, ate a delicious lunch, and still had time to visit the Aguas Blancas waterfalls before the day ended.


Once again, my heart breathed in the beauty around me — the farms, the mountains, the fresh air — and gave me a sense of belonging I hadn’t been looking for, but recognized the moment I felt it. That’s the thing about a real homecoming: it rarely announces itself. It just settles into you.


Food


Dominican food has always been farm to table, long before that phrase became a marketing line anywhere else. I noticed there are really two kinds of meals here. The traditional, which starts with breakfast: mangú (mashed plantains), alongside salchichón, egg, fried cheese, and coffee or fresh juice. Lunch is rice, beans, and chicken, pork, or beef, with tostones — fried plantains — served on the side. Sancocho, the classic stew, warms you up from the inside out.


Then there’s the second wave: international fusion cuisine, blending those same island flavors with global favorites. My favorite was goat over risotto — so unexpected, yet so delicious. What struck me most, though, wasn’t any single dish. It was how every meal was built around a table full of people. Long before I reached my own family, the island had already been showing me what home tastes like.


Family


Alberto drove me two hours to my family’s hometown. Along the way, I kept noticing how much the island has grown. The Dominican Republic is one of the fastest-growing economies in Latin America. In the past two decades, paved streets have replaced dirt roads, highways now connect the whole island, and Wi-Fi lets us stay connected to loved ones worldwide. Hiring a driver made all of it accessible, easy, and safe.


Thanks to GPS technology — which, ironically, Columbus did not have, or he might never have found this island at all — when Alberto pulled into my cousin’s driveway, my cousin was already outside, welcoming me before the car even stopped.


The next day, my aunt, my cousin, and I visited the ruins of my grandparents’ farm, where I took my very first steps. The land is thirteen acres, stretching back deep away from the road. In the back half, plantain trees have been planted, and cacao trees will be planted underneath once the plantains grow tall enough to give them shade — one generation of the land, quite literally, making room for the next.


With the main house already demolished, all that was left were the tile floors beneath my feet. With joy in my heart, I walked toward the run-down structure that used to be the kitchen and peeked inside. It was exactly as I remembered it, right down to the colors on the walls and counters, minus all the debris the years of abandonment had left behind. My cousin pointed to the well, dated June 26, 1974. Electricity didn’t reach that village until 1982. I smiled, remembering how neighbors used to press their faces against the windows because my grandfather was the first person there to own a television.


We also visited my grandfather’s youngest brother and his wife, both in their nineties, still living in the farmhouse where they raised their children. I sat and listened to the beautiful stories they shared about my grandfather, stories I had never heard, from people who had known him longest.


On my last day, a caravan arrived from Santo Domingo and Santiago. Cousins, aunts, uncles, and little ones I’d never met poured out of SUVs. When the family gathered under one roof, something clicked into place that I hadn’t known was missing. Fifty years ago, our family drew water from a well with no electricity in sight. Today, we have flourished. And a new generation of children — some growing up here on the island, others of us in the United States — will one day carry the next generation forward too.


That gathering wasn’t a goodbye party. It was a welcome home fiesta.


With faith in the unseen, Columbus set sail and found this island. With that same faith in the unseen — in roots that hold even across distance and decades — our family set out from a well with no electricity, and blossomed.
This is what roots feel like: arms around you, laughter overlapping across three generations, the faces that carried me before I could carry myself, and little ones who will one day carry the next generation forward.

Reunited, rooted, home.

You Built The Life. Now, Build The Love.

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Jianny Adamo, LMHC, LPC | fearlesslove.net

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Jianny Adamo LMHC
Jianny founded Fearless Love in 2011 one year after divorce to help couples reshape their legacy where their families can flourish. With nearly 20 years of clinical experience and an Amazon best-seller, she equips clients with tools for healthy communication, leadership and to shift from seeking certainty to anchoring themselves in the presence of love and connection.