Music floats over the thick, warm air, people dance at an outdoor café, two lovers sit on a bench staring into each other’s eyes, a man walks by calling out “pan, pan (bread, bread)!” and periodic bursts of shouting emerge from a pack of men enthralled in a game of Dominoes. In an attempt to stop perspiring for a minute, we grab a shady bench at the corner of this tree-lined park nestled in Santiago de Cuba, the country’s second largest city (and a must-visit locale), and settle in to absorb it all.

During our month-long bikepacking adventure through Cuba, we spent almost as much time soaking up the lively culture—full of music, dancing and celebration—as we did exploring natural wonders. When travel regulations eased, we were psyched, but ironically, we also felt an urgency to visit before it changed—one way or another. We arrived just days after Castro’s death to a country on the brink of big changes. It’s clear that this complicated island—with cars from the fifties, clothes from the eighties, and timeless beauty—has an eye pointed toward the future—whatever it holds.

If Cuba has been on your bucket list, it’s time to make a trip there happen. Here’s how we did it—with tips on outdoor adventures and the best ways to enjoy your visit.

Hike in Viñales

Most of Elevation Outdoors readers shy away from guided experiences, but a guide is the only way to explore Viñales National Park, an extraordinary reserve in western Cuba teeming with rich plant and bird life and where people live in harmony with the landscape. During our exploration with a park guide, we saw exquisite views of jungle-covered cliffs and limestone monoliths (mogotes) rising steeply from broad valleys where farmers cultivate the rust-colored soil. Our favorite part of this amazing journey: spending an hour at a small tobacco farm where Leonardo, a weathered, sombrero-clad guajiro invited us into a thatched shack. Surrounded by strands of dried wrinkled tobacco, he rolled us a cigar and explained the time intensive process required to turn seeds into the coveted Cuban cigarro puro.

Visit Trinidad & Playa Ancon

We ended up in Trinidad because the bus we wanted to take to Santiago de Cuba was booked—and we quickly fell in love with this quaint, colorful city, rich in cultural attractions and surrounded by stunning natural splendor. Our first morning, we feasted on a breakfast of tropical fruit salad, eggs, bread, cheese, ham, mango juice and amazing coffee accompanied by a local sound track—the clip-clop of horse hooves on cobble streets and of song birds chirping like a chorus. Then we hopped on our bikes and went to Playa Ancon, a sparkling white sand beach bordered by warm, salty waves. Though you can take a taxi here, the best way to enjoy the place is to rent a bike and take in a 37-kilometer (23-mile) loop ride that starts Trinadad. Head counterclockwise and it’s a magnificent adventure that traces the rugged, rocky coast near the small seaside village of La Boca. The return route rewards riders with a spectacular sight (especially at sunset): the turquoise waters of the Caribbean spreading before the lush Sierra del Escambray (Escambray Mountains) on the distant horizon. At night, hit the Casa de la Musica, an outdoor venue where locals and tourists gather to experience high-caliber Cuban  music and of course, to celebrate life by dancing until all hours of the night. Even if you’re not ready to strut your salsa skills, grab a seat, a mojito (or two or three), and absorb the palpable and contagious energy of the place.

Climb Cuba’s Highest Peak

Grueling. That’s the only word to accurately describe the hike up 6,476-foot Pico Turquino, a lush cloud-forest covered peak that rises straight out of the sparkling Caribbean sea. From Las Cuevas, a tiny village with no amenities, you gain almost 2,000 meters in 10 kilometers (6,562 feet in just over 6 miles) with very few switchbacks, also summiting Pico Cuba (1,872 meters, 6,142 feet), the country’s second highest peak on the way. This is officially a military area, so guides are required, so arrange the climb at the trailhead a day before or book in advance. Stay in a nearby town or if you don’t mind extremely rustic conditions, you can crash at the very basic visitor center the night before the climb. This is one of the most important historical places in Cuba, too: The Gran Parque Nacional Sierra Maestra, which holds Pico Turquino, is the remote jungle area where Che Guevara and Fidel Castro based their rebels when they undertook the revolution that overthrew dictator Fulgencio Batista and turned the island into a Communist nation.

Ride the South Coast

To experience raw natural beauty of the island itself, pedal the 180-kilometer (112-mile) road between Santiago de Cuba and Pilón, a small, isolated coastal town, famed for its blue waters and a style of music with its roots in the rhythm of pounding sugarcane. This wild, lonely route hugs the rocky shore, climbs over headlands and drops back down to the sea—it gets so close in spots that ocean spray kisses your face. (The ride made for some of our most memorable days on the island). Portions of the route are unpaved and washed out by recent hurricanes, but bikes can more than handle them. And road traffic is light. (Note: You can pair this ride with a climb of Pico Turquino).

Enjoy Santiago De Cuba

Fewer tourists venture to this capital of the southern province of Santiago de Cuba, 475 miles from Havana. It’s a short flight or a 12-hour train ride from the capital, but well worth the effort. The lack of foreigners here means this bustling city gives visitors a true sense of Cuba’s history and diversity. We enjoyed exploring the busy streets, which were always full of musical rhythms and chatter. For the best view in town and some solitude, tackle a series of steep, narrow stairs that lead to the bell tower of the Catedral de la Asunción, first built in 1514 when the Spanish began to colonize the island. It’s set a few feet from the right of the Parque Cespedes, a city square perpetually abuzz with activity.

Five Insider Tips to Know Before You Go:

1) Stay & Eat in Casa Particulars: 

Roll into almost any town and you’ll find a number of people ready to welcome you into their houses. These private homestays vary from a room in a house to a separate bungalow with a rooftop deck, but all share similar critical characteristics: private bathroom, affordable prices, stocked mini-fridge, a homey feel and the priceless opportunity to interact with warm, kind locals full of knowledge. Casa owners also cooked us tasty, authentic meals made with love that were, without fail, the best and most affordable food we ate in Cuba.

2) Be Flexible:

This isn’t the U.S. or Europe—why you’ve come—so bring realistic expectations. Avoid trains; they consistently break down, sometimes for days. Buses are more reliable, but there is no consistency regarding how you reserve a spot or buy a ticket. Buses are often full, so have a backup plan (go somewhere different on a whim that’s in the general direction you want to head) or spend an extra day or two in given location,until you can get a bus to your desired destination. Lines at banks and money exchanges often require at least half a day and restaurants may be out of a number of items on the menu. While they may seem hard to overcome (hint: Get to a bank a half hour before it opens or change enough money at the airport or a hotel so you don’t have to change any more money), these are minor annoyances, and your trip will be much more pleasurable if you can embrace the quirkiness of it all as part of the cultural experience.

3) Ride your bike or get your own transport:

Controlling your  movement throughout the country can help ease the challenges of dealing with unreliable transport (see “Be Flexible”). Pedaling bikes allowed us to move when and how we wished, and since many Cubans also ride bikes for transportation, we also had a more authentic exploration experience. Renting a car is always an option, however, you have to be comfortable driving in a place where traffic rules are very different and sometimes ignored.

4) Learn Spanish:

We didn’t find many Cubans who spoke English, but as Spanish speakers we didn’t worry.  At least learn the basics so you can order food, buy a bus ticket, get a room, follow directions and make conversation with casa owners.

5) Interact with as many Cubans as you can: 

Every local we got to know—casa owners, taxi drivers, guides and random others—won our hearts with their curiosity, politeness, openness and willingness to share their homes, time, dreams, hopes, beliefs and honest thoughts about the US and about Cuba. Though the astounding beauty and the vibrant music made an impression, the warm, proud people, who were outwardly passionate about country, family, learning and finding out about the rest of the world left an indelible mark on our hearts.

By Chris Kassar 

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