Stroll through history in Dominican Republic's underappreciated capital

"You need haircut," yelled a barber. "Come," he said, waving his hand for me to enter his shop. Before I reached the next block, at least four other barbers accosted me. I was on El Conde, the bedraggled pedestrian street that cuts through the heart of Santo Domingo's charming Zona Colonial. Apparently I'd just stumbled upon the Aggressive Barbers Zone.

I didn't actually need a haircut. At least I didn't think so. But the Dominican Republic capital, the largest city in the Caribbean, was refreshingly free of tourists and so I had a target on my back, or in this case on my apparently hairy head.

Santo Domingo is largely a mystery to the average tourist, who's lured to the long, wide beaches and all-inclusive resorts in Punta Cana and Puerto Plata. Sipping a Coco Loco with my toes in the sand certainly sounded tempting, but the capital — the oldest European city in the Americas, founded by Bartholomew Columbus, the younger brother of Christopher, in 1498 — promised cobblestone streets, sprawling plazas, late-Gothic cathedrals, ancient palaces, fortresses and monasteries. I decided to explore this underappreciated city, strolling its cobblestoned streets, eating porky Dominican dishes and chatting with locals.

Santo Domingo is a city of firsts: the first paved street in the New World (Las Damas), the first stone structure (Casa del Colon), the first cathedral (Catedral Primada de America), the first monastery (Monastery of San Francisco), the first convent (Convento de la Orden de los Predicadores), the first hospital (St. Nicolas de Bari), and the first military structure (Ozama Fortress).

So it seemed fitting that my base would be the city's first boutique hotel. Casas del XVI is smack dab in the middle of this compact old quarter, a UNESCO World Heritage Site known as the Zona Colonial. When I checked in, the 20-something front desk clerk, Albin, greeted me with a glass of passion fruit juice and a promise: "Our policy is that we'll go out of our way to do anything to help you while you are here," he said, and then added: "Anything you want."

For now, I just wanted to wander. I set out, walking down cobbled streets flanked by low-rise, brightly hued buildings, as the sun beat down on me and my olfactory glands were treated to wafts of pork-accented scents from nearby open-air restaurants.

At the Catedral Primada de America, a stone structure built in 1515 by Christopher Columbus' son, I stood in the middle of the nave, staring up at the soaring ribbed gothic ceiling, thinking that the church seemed like it was picked up in Spain and dropped here. There was nary another tourist in the place. As I strolled down Calle Las Damas, a sightseeing trolley puttered past me, its two carriages sprinkled with a few tourists as the running commentary explained we were on the first paved street in the Americas.

It seemed that I nearly had the entire city to myself and the locals. Later that night, I ambled down the twisting Malecon, the coast-hugging boardwalk, until I reached Adrian Tropical, one of the few restaurants to take advantage of the city's seaside location. I ordered up a bowl of addictive sancocho, a stewy local dish bobbing with an everything-but-the-kitchen-sink list of ingredients: succulent pieces of pork belly, yucca, plantains, cilantro, garlic, small ears of corn, avocado and just for good measure, chicken. If I weren't so full, I would have ordered a second bowl.

So far I'd only made basic requests to my hotel concierge, such as restaurant recommendations, but the next morning I decided to conjure up something that might be more challenging.

"Anything you want, Mr. David," said Albin.

"It's a bit strange," I said, as Albin's eyebrows raised up a bit. "I'm looking for an antique wooden leg." I didn't really want a wooden leg. I just tried to think of something obscure. Albin cocked his head and squinted his eyes, so I mimed the international hand sign for leg amputation, pretending to saw off my limb at mid-thigh.

He tilted his head back and laughed. "This is the strangest request I've ever had. But OK, I will get on it."

It was Sunday and common wisdom would suggest the city would slow down for the so-called "day of rest." Not in Santo Domingo. A friend in New York told me that the common Sunday activity here was going to the car wash. I was baffled. "Seriously," she said, "go see for yourself."

So I did. As I walked up to the car wash, Pasteur 8, a 15-minute stroll from the Zona Colonial, I noticed something odd: Customers waiting for their cars to be cleaned were nursing large bottles of beer while watching a baseball game on TV. I snuggled up to the bar, ordered a beer and asked the guy next to me if it seemed questionable to combine driving and beer drinking. "The car must get clean," he said, laughing. "This is the D.R., mi amigo. Everything you know about rules is different here."

I looked around and saw families playing billiards and, for those who preferred to take swings rather than swigs, there was a batting cage.

With the sun ready to sink into the horizon for the night, I walked across the Zona Colonial to the ruins of the monastery of San Francisco. Every Sunday evening there is a free live merengue concert, a native style of music known for its fast, up-tempo and funky Latin beats. I stood toward the back sipping a local beer, Presidente, watching a 12-piece band on stage tear it up as about 400 locals gyrated their hips and bobbed their heads.

This is not music, I thought. This is a trip. It's Santo Domingo wrapped up in a tiny swath of the city, everyone here united by the music: from well-dressed wealthy people to the working class, all drinking cold beer and dancing.

When the show was over, I zigzagged through the streets feeling fulfilled by Santo Domingo. I eventually returned to the hotel and saw Albin, the concierge. "I'm so sorry, Mr. David. I called every antique store in town. No one has a wooden leg for sale. I think there is not one in the entire country." And then he asked: "But if there something else I can do for you, please let me know."

This time I decided to toss him a softball. "Any idea where I can get a haircut tomorrow?"

He had several suggestions.

David Farley, a Berlin- and New York-based food and travel writer, is a contributing editor at Afar magazine.