Armed with a keen sense of adventure, the author heads to Cuba’s southern coast, where the driving is a challenge but the sites are more than enough reward.

By Carey Jones
April 04, 2016

I started planning a return trip to Cuba even before my first one ended. It wasn’t the jazz clubs, the chaotic energy, or the ’57 Chevys that gripped me—though they’d no doubt lent a hand. What I couldn’t shake were images from the few short forays I took outside Havana: elderly cowboys near sputtering classic cars, pig roasts at mountaintop cabins, and little-trafficked roads cutting through vast tobacco fields. The city, I quickly realized, is just the beginning; beyond it, there’s an entire country to be seen.

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So within a matter of months I returned with my fiancé for a three-day road trip across the country’s southern coast. We wanted to find the small colonial cities that friends had described as so stuck in time they’d make Havana seem modern. Along the way, we discovered that Cuba’s wide-open highways and mountain roads are just as fascinating as the destinations they lead to.

Day 1: Driving then Drinking

After picking up our car—a Chinese-made sedan, one of the few rental options from the state-run agencies in Cuba—we fought our way through Havana’s frenetic sprawl to Autopista Nacional 1, the highway running down the island’s spine from Havana in the northwest to Sancti Spíritus in the island’s center. The road was an adventure in itself. Over the course of our four-hour drive, my fearless fiancé dodged hitchhikers, bicyclists, and overloaded horse-drawn carts. And that’s not to mention the scratched-out signposts and potholes—some so deep that dogs could use them as bathtubs. Navigating was almost as great a challenge: paper maps are an absolute necessity, as most cellular carriers have no roaming service here. Needless to say, driving in Cuba will make you feel accomplished, like you’ve survived some kind of initiation.

With its pastel-painted houses and cobblestoned streets, the town of Trinidad—a UNESCO World Heritage site—provided the picturesque welcome we’d hoped for. What we didn’t expect was to be surrounded by as many horses as cars in the town center; we drove at a crawl, eventually parking near the pedestrian-only Plaza Mayor and our home for the night, Casa Arcangel. 

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Cuba’s system of homestays, or casas particulares, is like a low-tech Airbnb, and pre-dates that company by more than a decade. Some make you feel like you’re staying in a family’s snug spare bedroom, while others are more like professionally run inns. Casa Arcangel falls into the latter camp, with an outdoor courtyard for breakfast and two rooms for rent, each with beautiful colonial furnishings. We joined Miguel, Arcangel’s genial young proprietor, for beers on the rooftop; then out came a bottle of Havana Club 7-Year and Miguel’s entire extended family. Experiences like this, we thought, are exactly why a casa particular will always trump a government-run hotel.

Miguel’s cousin Sheyla corroborated our hunch that in Cuba, whitetablecloth restaurants tend to be stuffy and uninspired. She pointed us instead to Taberna de Botija, a tavern beloved by locals with walls covered in curious historic ephemera. There, we happily devoured traditional Cuban dishes like brochetas, skewers of tender beef and vegetables grilled over a charcoal fire.

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Next, we sought something a bit more lively. “Trinidad has the best nightlife of any Cuban city,” my friend Jesús Noguera, a Havana-based tour guide, had told me. So we followed a distant hum to the steps off the Plaza Mayor, where percussionists with conga drums, animated singers, and trumpeters were gearing up for an outdoor salsa fest. In Trinidad, as in many Cuban towns, nightlife is a community-wide affair, with twirling teenagers and jumping children and grandparents far more graceful on the dance floor than your average septuagenarian. Swept up in the energy, I found myself thankful for the single Latin dance class I’d once taken.

Day 2: History in Motion

Before we left Trinidad, I wanted to catch a glimpse of the Museo Romántico. Set within the 19th-century Palacio Brunet, it’s a prime example of colonial architecture; it’s also styled as a home of the era, from period furniture and art right down to china and textiles. The opulence served as a reminder of the onetime wealth of this small city—echoed only by the grand buildings flanking the Plaza Mayor. On our way out, we made an impromptu detour into the surrounding side streets, where vendors had set up stalls selling crafts; I couldn’t resist picking up a delicate piece of lacework and a sturdy handwoven straw bag.

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Then it was off to Cienfuegos. The scenic route, Carretera Sur, hugs the country’s southern coast, heading west into the green foothills of the Sierra del Escambray mountains. We saw houses ringed by fences of cacti; kids playing in a waterfall; two men in straw hats, cigars between their teeth, chatting on horseback. And once again, terrible road signs, which failed us repeatedly. But locals proved helpful. One older man guessed from our tourist car that we’d taken a wrong turn and, amazingly, ran behind us to offer directions.

First settled by French immigrants, the waterfront city of Cienfuegos is also known as La Perla del Sur—the Pearl of the South—and it still has a distinctly colonial feel. The town’s main sights cluster around the Plaza José Martí; of the surrounding monuments, I loved the Catedral de la Purísima Concepción, with its vaulted ceilings and ornate stained glass, and the Teatro Tomás Terry, a 19th-century theater with original frescoes that’s still in operation.

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A short but scenic drive down Punta Gorda, a landmark-lined peninsula jutting out into the bay, led us to Perla del Mar, one of Cuba’s only boutique hotels, in a renovated 1950s mansion. We settled into our light-filled room (one of nine), turned up the air conditioner, and enjoyed a brief escape from the tropical heat.

We couldn’t help but notice the Palacio de Valle, just across the street. The 100-year-old Spanish-Moorish estate is the town’s premier architectural site; these days, it’s been converted into a government-run restaurant, better known for its stately cupolas and intricate murals than for its food. So we saved our appetite and went for a daiquiri on the terrace, which has panoramic views of Cienfuegos Bay.

Once the sun had finally dipped below the horizon, we set off on a five-minute walk to our dinner spot, a live-fire place at the very tip of the peninsula. Our table at Restaurante Villa Lagarto was close enough to the waves to feel the occasional sea spray, but more memorable than the setting was the food: showstopping stewed rabbit and fork-tender suckling pig with skin as crispy as cracklings. My fiancé, a cocktail consultant by trade back home in New York, gushed over the rum selection, which included Havana Club bottlings we had never seen before. In the name of research, we ordered shots for dessert.

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Day 3: To the Beach

I knew we were nearing the Bay of Pigs when we began to see billboards emblazoned with slogans like ¡HASTA LA VICTORIA SIEMPRE! AND ¡IMPERIALISMO NORTEAMERICANO! Americans, if not their government’s policies, are generally embraced in Cuba, yet reminders of our fraught historical relationship abound. (In the small town of Playa Girón, where the historic invasion made landfall, the Museo de Playa Girón offers the Communist version of the story.) Now the area, called Bahía de Cochinos in Spanish, has turned over a new leaf, having emerged as a rising snorkeling and scuba destination with plentiful marine life just off its shell-strewn beaches. For the prettiest swims, we were told to head to Caleta Buena, a protected cove with iridescent blue waters five miles east of Playa Girón. The water was so clear, you could see entire schools of rainbow-colored fish from above the surface, but I put on some flippers and dove in for a closer look.

A few hours of sunshine later, it was time to get back in the passenger seat and unfold our dog-eared map again. This time, we welcomed the inevitable obstacles—the longer to keep us there, I thought—as we wound our way back toward Havana.