Fearless Journeys in the Dominican Republic: A Week of Craft, Culture, and Connection
Our most recent Fearless Journeys experience took us to the Dominican Republic for four incredible nights in February — and what a journey it was.
Our most recent Fearless Journeys experience took us to the Dominican Republic for four incredible nights in February — and what a journey it was. In partnership with a rising boutique cigar company, Don Doroteo Cigars, we spent several days connecting with entrepreneurs in the cigar industry while exploring some of the most historic and scenic parts of the country.
We began in Santiago de los Caballeros, known as the cigar capital of the Dominican Republic. After checking in at Camp David Ranch — a mountaintop hotel with sweeping views over the city — we were transported down into the valley to the Don Doroteo farm. There, founder and CEO Juan Lugo, along with several of his business partners, welcomed us with a tour of the fermentation barn and an overview of the family legacy behind the brand.
That evening, we gathered in the open air at the farm, cigars in hand, and enjoyed a flavorful spread of Dominican cuisine by Chef Marlon Nuñez. It was a relaxed and welcoming setting — the kind of environment that naturally invites good conversation. Later that night, back at Camp David, we wound down looking out over the lights of Santiago. Something about being up on that mountain invites reflection.
The next day, we toured La Aurora, the oldest cigar factory in the country. It’s a massive operation, but what stood out wasn’t just the scale — it was the attention to detail, the pride in craftsmanship, and the values woven into the company culture. The company creed was adorned in the entry way, the walls around the factory were covered with quotes from innovators like Henry Ford and Steve Jobs, and the workplace benefits were remarkable, including unlimited cigars for employees during their shifts. It was eye-opening to see how tradition, innovation, and care for people can all thrive under one roof. And our guide Eugenio was a character we will certainly remember forever!
That night, we returned to the Don Doroteo farm for what was, for many, the highlight of the trip — a five-course dinner in an outdoor gazebo surrounded by towering tobacco plants. Toward the end of the evening, Juan and his team surprised us with a rare treat: a 21-year-aged cigar called El Vencedor, not yet released to the public. It was a generous gesture, and the kind of moment that made the whole group pause and appreciate where we were and who we were with. That it also happened to be Valentine’s Day felt symbolic — many of us found a new appreciation, if not love, for the craft and culture behind cigars.
On Saturday morning, we left Santiago and headed north toward the coast. Along the way, we stopped at La Isabela, the site of Christopher Columbus’s first permanent settlement in the New World. Standing on that ground was humbling. We saw the foundations of Columbus’s house and the ruins of the first church built in the Americas. For all of us — especially those with an entrepreneurial mindset — it was a powerful reminder: great journeys often start small — with a vision, a few believers, and a bold leap into the unknown.
A short drive away, we had lunch at Fricolandia, a quirky, beachfront restaurant with incredible views of the Caribbean. From there, we continued on to our final stop: an all-inclusive beach resort in Puerto Plata, where we recharged and caught the sunset with new friends and fresh cigars.
That evening, we were joined for dinner — and cigars — by Justin Neat, one of the co-owners of Don Doroteo. What stood out most about him wasn’t just how much he knows about the cigar world — and he knows a lot — but how generous he was with his time and insights. The conversation meandered from business to life to everything in between. It felt like talking with an old friend, which became a theme for the rest of the group as well.
On Sunday, we traded cigars for helmets and life jackets and headed to Damajagua, where we climbed, slid, zipped, and splashed our way through seven waterfalls, five zip lines, and two suspension bridges. It was a physical adventure, but also a personal one — pushing past hesitation, laughing through the nerves, and sharing in the kind of joy that only comes when you step a little outside your comfort zone.
That night, we gathered for one final dinner at the resort’s Japanese steakhouse and enjoyed a last round of conversation over cigars at the open-air lobby bar. By then, the group felt more like a family. And as we eased into our final morning — a quiet President’s Day with time to sleep in and enjoy the beach before heading to the airport — there was a shared sense that something meaningful had happened here.
What made this trip special wasn’t just the cigars, the waterfalls, or the historic sites — though all of that was unforgettable. It was the people. Our travelers came from different cities and backgrounds, but by the end, we had forged connections that will carry on well beyond the trip itself.
While the Fearless Journeys community extends far beyond our group trips, it was founded on the belief that travel can be more than escape — it can be a catalyst for growth, connection, fresh ideas, and real-world learning from the entrepreneurs we meet along the way.
Our four nights in the Dominican Republic were a clear reminder of why we do what we do. I’m grateful to everyone who joined us — and to our partners at Don Doroteo — for making it all so memorable.
We’ll smoke to that.
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Since leaving the DR, we have now launched Fearless Journeys 2.0. Check out our new website and apply to join us the 2.0 community today so you can get invites to our future trips and other Fearless Journeys experiences.