Adventure, Dominican Republic, Favorites, The Great Adventure, Travel

Coming Home from the Caribbean with Doubts

Calle José Reyes

I caught Jessica’s eye. She nodded. She remembered the rule: never ask a Santo Domingo cab driver how much the ride will cost. Just wait till you get there and pay him what you think is right. It’s 170 pesos to go anywhere in the city, 150 if it’s very close. (The airport is more.)

This one was busy scribbling his personal cell number on someone else’s business card, telling Jess in Spanish that we should call him for all of our taxi needs. She added the card to four others in our collection. We’d been in the city all week, adding paved streets and outdoor cafes to our otherwise backpack-and-bus style trek across Hispaniola. We had escaped here for two months, to explore villages, beaches and our fledgling love while dodging deberes at home.

The problem was those two months were over.

We had spent the first half of our time mostly in one town, Las Galeras, doing our work in the mornings and taking afternoons in the sun. “Galera,” as you’d say in cotton-mouthed Dominican Spanish, was not exactly a cute little fishing hamlet, but it also wasn’t a thumping resort destination, and that’s why we stayed.

By our second month we were ready to strike out. We crossed the DR end to end (some of it more than once) and we went to Haiti. It’s hard to describe everything that’s wrong with Haiti, but I can say that getting up in the morning and leaving the house feels like being hit in the face with a plank. I told Jessica it was the roughest trip I’d ever taken.

“It’s not my roughest ever,” she said. “But I’m the oldest that I’ve ever been.”

Returning from Haiti instilled in me a new sense of adoration for the Spanish side of the island, home of a laid back people who add sugar even to fruit juice and lift their shirts over their bellies when they need to cool off. I had come to feel at home here, to feel happier than I do in most US towns, and now it was time to leave.

Papa Legba

Papa Legba at the Hotel Oloffson in Port-au-Prince, Haiti.

Before I began my travels I had the idea that travel changes the mind. I pictured that traveling far and wide would, on its own, be some kind of transformative practice—that the adventures I’d find myself in would refine who I was. That’s essentially true, but I don’t think I could have imagined how it actually works.

Travel is not an adventure game where overcoming challenges develops new skills, or where mentors and allies appear to help you through the toughest times. Travel breaks you down. Most of the new skills you gain are developed during the many, many times you fail to overcome challenges, and more often you feel like you’re gambling your way forward with a skill set that’s far from sufficient. Mentors and allies can be found, but you generally have to create those relationships yourself—you have to take a lot of social risks.

The result is that travel does change you, deeply, but not by simply powering you up to some kind of super-talented globetrotter. If anything, travel changes you most effectively by undermining your sense of self, your certainty. It forces you to rethink things you believe.

Such as your purpose in life.

This is a pillar of heroic philosophy, the idea that simply going out and adventuring will bring you in contact with your calling, whatever that might be. For me, that has meant not only discovering new truths about myself, but also letting go—sometimes painfully—of things I was convinced I wanted.

Having shed so many of my old beliefs on the 1,800 mile bike ride, I didn’t expect another shakeup, not anytime soon. I felt a renewed sense of purpose during my stay in New Orleans, a certainty of my next steps: bike to Texas. Now, on buses and beaches and completely off-track, I would slip into daydreams and wonder what I could do instead.

The walking mall (Calle el Conde), Santo Domingo.

The walking mall (Calle el Conde), Santo Domingo.

Our last days in Santo Domingo were filled with exploratory strolls down old colonial streets, hand in hand, talking about anything besides what next. In the evenings we went to the hidden Cuban restaurant, where Serge would bring us mojitos and picaderas, a rocks glass of rum in his hand like he was our uncle at a family dinner. No one but us came in; “Dominicans don’t like anything different,” Serge said.

It was a sentiment I could relate to. Our life had become an idyllic one, traveling the Caribbean with just enough money, our Spanish on the mend, our love getting cozy. Why would I want anything to change?

The truth is, I didn’t.

As we walked I would think about the busy, hard life of writing while bicycling. I would think about how I imagine Texas and rural Louisiana, about camping in a small hammock illegally by the side of the road, about dodging semi-trucks and eating at gas stations. I found it hard to stir up any flavor of zeal for returning to that life.

It really wasn’t about my relationship with Jessica. We figured that out with relative ease (eventually): she’s going to come visit me in Texas when I reach it, and we’ll take it one step at a time. My crisis of the last few weeks was really, it turns out, about my own future

Angel Urrely, "Deforestación de la jungle a la botánica," in the Museo de Arte Moderno in Santo Domingo.

Angel Urrely, “Deforestación de la jungle a la botánica,” in the Museo de Arte Moderno in Santo Domingo.

We went to the Plaza de la Cultura, a cluster of national museums tucked somewhere between a university, the US Embassy and Santo Domingo’s only real freeway. We had just a few hours, so we chose in advance to see (only) the Museo de Arte Moderno. Had we known what we’d find, we would have gone for a whole day.

The Plaza is more like a campus or a private park. We strolled among fountains, massive trees and oh-so-rare green space. At first we couldn’t understand the peculiar sense of enchantment we found there, until we realized: it’s the only place in Santo Domingo that’s quiet.

That silence and magic stuck with me. Latin America takes art and scholarship seriously in a way that my home culture simply doesn’t. There’s a special reverence for education, and in turn for academics who devote their lives to study. Philosophic questions are fare for casual conversation. In the United States a PhD is a “piece of paper”; in the Latin world it is proof of real knowledge, knowledge that can change the world.

Inside, I clicked into my museum mode. I overflowed with questions about technique and meaning and artist intent. I had sudden ideas for new works of art. At closing time the docent had to kick us out, me fighting to snap pictures of artist names so I wouldn’t forget them.

It was there, strolling at sunset through a temple of culture, that I glimpsed a life I could be happy with. Not working in a museum; I had done that already. Not becoming an academic, necessarily, though I’ve long considered the option of grad school once I finish my journey.

But I could see myself in that world, somewhere in the intersection of culture, education, creating art as a writer, and connecting people as a traveler.

In other words, I’m not so sure my purpose involves less adventurer in “philosopher-adventurer,” but it does likely involve more philosopher. 

Me having fun covered in mud.

Me having fun covered in mud.

Jess and I flew back. She’s in New York, on business, but she left me her apartment. For a few short days I have the bliss of sunny windows, good wi-fi and no distractions: the perfect place to write.

Then I need to leave.

New Orleans is my favorite American city—our least American city—but what I love is Latin America, every part of it I’ve been to. I don’t want to be in the United States, not temporarily and certainly no longer than needed. That means I need to rethink whether I want to spend many months training in Texas so I can kayak south.

I thought my purpose in life was to be an adventurer, to set great and near-impossible tasks and then push myself till I complete them. That 8,000 mile trek to Brazil still appeals to me.

But my journey makes me question that purpose (that is, after all, what journeys do). It makes me wonder: would I be happier getting there faster, living longer in fewer places, writing all day instead of biking all day?

And if I would be happier with that, why delay it another four years with this great trek?

I will at least go as far as Texas on the bike—and maybe keep going. By this time next week I will, indeed, be camping illegally by the side of the road. I will almost certainly be eating at gas stations. I will be following a dream I’m not sure is possible. And I won’t know why.

Some part of me says: because it’s what you’re meant to do. I’m just not sure I can trust that part of me.

Adventure, Dominican Republic, Spotlight, The Great Adventure, Travel

How would you like to be part of a tale of love?

This is Jessica’s take on our first two weeks running away.

“How would you like to be part of a tale of love?”

This is what I was planning to say if anyone opened the door. It was June 27 and Drew and I were just walking by this mansion on St. Charles Avenue. We had spent the past few days talking about “hypothetically” going to the Dominican Republic for two months to live on the beach and work and be together, and today was our decision deadline. It had been a rough afternoon: he wanted me to go, I wanted him to understand I couldn’t go. We were exhausted, and were walking to Fresh Market to get sushi. I told Drew we should stay in New Orleans together. He looked up at the beautiful house and said, “I’ll stay if we can live there.” He didn’t think I would knock on the door.

I climbed the stairs and rang the bell. While we waited for someone to answer, I pondered what I could possibly say to them.

A tale of love. It didn’t work out that way. No one answered the door. We knew we weren’t staying in our sweet New Orleans together. We ate our sushi. But late that night I gave in. All my anxiety about running away together, about not going to my familiar and comfortable New York with my old friends—it was all outweighed by the horrible sinking sadness I felt at the thought of Drew getting on his bike and me getting on a plane and that being the end of our adventure.


Nothing Left to Fight About

So here we are. I think we argued constantly for the last week before we left. We fought about money and time and whether we wanted air conditioning in our house. [Drew’s note: air conditioning is not bueno!] By the time we got on our 6 a.m. flight out of New Orleans on July 4th, I hoped there was nothing left to argue about. When we got upgraded to business class from Atlanta to Santo Domingo, things started looking up.

We landed in Santo Domingo with plenty of time to get to the bus to Las Terrenas, a town in the northeast that a friend had told us had “a few things going on.” We walked around, shouting over the constant roar of motorbikes in the street. We had a good but expensive dinner in town and a cheap but terrible night of sleep in our hot, buggy hotel. In the morning we got on a gua gua to Las Galeras, two hours further out on the peninsula and rumored to be quieter than Terrenas.

It’s definitely quieter. There’s a street and two beaches and a few places to eat, most of which we can’t afford. There are three dive shops and lots of guys offering rides on their motoconchos (motorcycle taxis). We looked at a half a dozen hotels before we found the best one in town, Hotel La Playita, which has a swimming pool and a sweet Spanish manager named Argentina.

La Playita Hotel, where we live.

La Playita Hotel, where we live.

On Saturday we started looking for somewhere to live. By the end of the day, we’d seen eleven houses, including one where the bathroom was IN the bedroom and another which was fully furnished—including some dude and his clothes. We saw a beautiful guesthouse behind a French lady’s villa, but she wanted more than double what we wanted to pay.

“It’s the low season,” we reminded her.

“I don’t care,” she retorted. “I’m not a business person. I live here.” We left.

We liked a two-story house near the beach. It was in a resort that was closed for the summer while the Canadian owner was away; she had left the resort and her dog, Leika, in the hands of 24-year-old Ruth (locally pronounced “hoot”), who sat in the empty restaurant all day in case someone came in. We skyped with the owner and negotiated her down to US $650 for the month—a little more than we wanted to pay, but worth it, we thought, for the privacy, two rooms, and proximity to the beach.

Bad choice. The wifi didn’t work, the lightbulbs were all burnt out, and the couch was so filthy that Drew resolutely refused to sit on it. The next afternoon, we were back on skype with Ms. Canada, trying to get our money back (which we did—most of it.) That night, we hustled back to La Playita and Argentina, and that’s where we live, at least for now.

Hand Us the Bill

Our first full week was full of adventures, misadventures, some highs and some lows. We figured out how to get water: preferably NOT from a guy called Wino who drives around in a pickup truck with “Supermercado Numero Uno” painted on the side. Numero Uno apparently stole a cell phone from an Italian guest at our hotel. And we tried to take Spanish classes from a terrible teacher named Armando, who gave us a textbook with his face on the cover and spent way too long teaching us the names of genitals in Spanish.

[Drew’s note: he drew a nipple on the whiteboard.]

Within a 10 minute walk from home there is one beautiful beach, where we swam, drank a coconut, and met some cool Israeli travelers; and one less beautiful beach, where we stumbled around in seaweed. A hike along a muddy horse trail covered in rotten mangoes deposited us at the most startlingly beautiful (and empty) beach we’ve ever seen, Playa Colorada.

The house where this happened.

The house where it all started. Jess really did knock on the door.

We’ve been unable to meet the local Peace Corps chica despite stalking her relentlessly for two weeks. We have, however, met a handful of other local characters.

Alejandro and Raisa run a small eatery on our street. They never seem to have what we want, but someone always runs across the street or across town to get it for us. Alejandro always has an offer: a cheap house, a cheap motorbike, and, most recently, the pleasure of his company on our travels. “I want to hang out with him,” Drew says, “but I’m afraid somehow the situation is going to end up with him handing us a bill.”

“Jessica’s mom” is a Haitian woman who runs a fruit stand with a sign that says God protects this business. We don’t know her name, but the first day we met her she was in a store yelling “Jessica!” I kept turning around until I realized the toddler with her was also named Jessica. Now whenever she sees me she yells, “HOLA, JESSICA!”

Pucho sold us some rusted bikes with busted gears. Tomeo is a bald and rotund Spanish man, jovial but world-weary, who I think has the potential to be BFF’s with Drew, as soon as they can get a language in common. Adrian, a high energy five-year-old, might as well be our shadow; Martina, who’s Italian, speaks not a lick of Spanish but doesn’t let that stop her from talking your ear off; and then there’s “Se Vende” the motoconcho driver. He couldn’t get us as a fare so now, every time he sees us, he tries to convince Drew that he should BUY his motorbike.

Food options are limited. We call our favorite restaurant Darny Mart after the friendly owner who sometimes makes eggplant. It’s a nice change from the daily monotony of rice and beans and chicken. When Darny’s not around, the woman who works there eyes us with such hate that it makes the hot sauce turn cold. On those days we escape to Manuel’s panadería where there’s something resembling pizza and, occasionally, chicken on a grill outside. There are a lot of places serving fish, which is not surprising since we’re five steps from the ocean. What is surprising is that a seafood dinner is usually twice the price of chicken.

Under the Stars

Despite the stress of trying to live and work in what is basically a glorified hotel room, we laugh constantly. This town is hilarious and ridiculous and sad and awesome. We have it pretty good: for US $385 a month, our apartment includes a pool, (almost) daily maid service, laundry, all the coffee we can drink. We also have Argentina and her husband, José, watching out for us when we lock ourselves out of our room or need a vegetable peeler or suddenly have an inch of water all over the bathroom floor.

We still don’t know what the hell we’re going to do in 6 weeks, when we fly back to New Orleans and Drew has a birthday and our paths diverge once again. But for now, we’re breathing clean air and looking at the stars and swimming in the ocean and being grateful that we’re able to live our dreams and be on this crazy adventure.

Jessica is a location-independent market research consultant. For twelve years, Jessica has designed and executed research programs for clients including top academic institutions, Fortune 500 companies, and grassroots community groups.

Adventure, Dominican Republic, The Great Adventure, The Heroic Life, Travel

The Change In Plans

Jessica and Drew

So much has changed in only a week.

The crossing of the Mississippi was successful. After many well-intentioned warnings, it was almost comically easy: I can’t imagine a more pleasant kayak trip. I can say that Jessica was as tough and capable a partner as one could hope for. She has my heart.

And that’s the thing.

As any reader should know, I finished my time in New Orleans and tuned my bike for 700 more miles. Those 700 will take me to Corpus Christi, Texas where I’ll train on sea kayaks until I can paddle the Gulf of Mexico.

Saturday morning the Giant was all loaded up. At the morning send-off party I popped the champagne, put my arm around Jessica, and made the announcement:

“There’s been a change in plans.”

Jessica and I are running away to the Caribbean.

Taking Risks for Love

I will still bike to Texas, paddle Mexico, walk to South America. But Jessica and I haven’t had enough of each other. So we’re both taking a risk.

For me it means delaying the next stage of my Adventure; for her it means cancelling a summer in New York. We’ll spend the next two months together in the Dominican Republic, in a small village on the beach.

Is this crazy? That’s certainly the word we both use. We’re nervous. I don’t really know if this is the beginning or the end. But together we’ll explore deserted beaches, scramble up waterfalls, motorbike through mountain towns. I’ll learn to cut coconuts with a machete, and maybe we will be happy.

It is right to take risks for love.

This is temporary. In August we’ll fly back to New Orleans—hopefully with a clearer picture of what we want for our future—and I’ll resume my trip from exactly where I left off. The Adventure will go on.


At many points, when the going was hard or temptation reared her head, my friends have said it’s okay if I don’t complete the Adventure. I’m sure that many of you share that sentiment, too—it’s meant in the kindest way, and I appreciate that.

But I care.

I care whether I complete the Adventure. It’s not optional to me. It’s woven in my nature, it’s assigned by my highest self.

There will be a day when I limp, drift, raft, stumble, bike, run, or race the last 18 steps and my heart will be complete. I will know I lived a story and I will know who I am and what I must do. Until that day, I take a step forward, a cautious step forward.

And here’s what so few people know: I care about completing the Adventure, but I don’t care how long it takes.

Running away for love is not, to me, a delay in the Adventure. It is the Adventure.

We had joked about this idea for weeks, always a joke. But then reading, researching, looking at what it would take. I told Jessica we had to make a decision. She said no, I can’t do it, I can’t just run away for love. So I packed my bike.

The next day she held me and breathed: let’s do it. “We have to do it.”

And so we do. Set my bow at the storm, let us sail this ocean again. Let us sail the ocean of fear and trembling, because what else is there? Only islands, islands in the storm.