Rhythms of the Road: A 12 Day Cuban Motorcycle Adventure
From the bustling streets of Havana, white sand beaches of Playa Larga, to the tobacco fields of Viñales, discovering an island of stunning landscapes, complex history and unbreakable human spirit.
There is no way to truly understand Cuba from the window of an air-conditioned tour bus. To feel the pulse of this complex, beautiful, and challenging island, you have to be fully exposed to it. For the past 12 days, that’s exactly what we did—straddling a BMW F700GS motorcycle, navigating a 1,500-kilometer loop that took us from the iconic capital to remote mountain villages and glittering coastlines.
It was an adventure of stark contrasts: pristine Caribbean beaches and crumbling Spanish and French colonial facades with Brutalist Russian architectural legacy; incredible mountain switchbacks and pothole-ridden highways; a history of revolutions, fierce independence and a present reality of profound economic hardship.
But above all, it was a journey defined by the Cuban people. Their warmth, resilience, and vibrant spirit shone brighter than the tropical sun, even against a backdrop of daily struggles.
Here is the journal of my two-wheeled adventure through the heart of Cuba.
The Practicalities: Entering Cuba
Before revving the engines, a note on logistics. Despite its political complexities, entering Cuba for tourism is surprisingly straightforward.
Flights & Visas: Most travelers need an “Electronic Tourist Card” (often interchangeably called a e-visa). and you will have to complete your D’Viajeros Form, very easy process (you should not need to pay for someone to help you, contact us if you need help) that you can do entirely online before departure. American Airlines e-visa info
Arrival Process: I was expecting a bureaucratic nightmare, but the process was incredibly easy and smooth. Customs documents were simple, the immigration queue moved very fast and the officials were courteous and professional. Within an 30 min of landing in Havana, I was out in the humid air, ready to take on new adventures. There is a limit of $5000 usd you can bring in cash but if you need more (not sure why you would) you can bring more, you just have to declare it at the airport
A Primer: The Layers of Cuban History
To ride through Cuba is to ride through layers of intense history. You see it in the architecture, the faces of the people, and the monuments by the roadside.
The First Peoples: Long before Columbus arrived in 1492, the archipelago was inhabited by indigenous groups, primarily the Taíno and Ciboney peoples. They were skilled farmers and fishermen living in complex social structures. Sadly, disease and brutal colonization wiped out most of this population within a few decades of Spanish arrival, though their legacy remains in Cuba’s vocabulary, food, and genetic makeup.
The Revolutionary Shadow: The modern era is, of course, defined by the Cuban Revolution, culminating in 1959 when Fidel Castro’s 26th of July Movement overthrew dictator Fulgencio Batista. Whether you are in a city square looking at a mural of Che Guevara or riding past agricultural collectives, the political structures established during that era still dictate daily life today.
The Journey: A 12 day Loop
Part 1: Havana and the Southern Coast
Starting in Havana is a sensory overload. It is a city of faded glory, where magnificent colonial architecture stands in various states of disrepair, teeming with life, music, and the omnipresent scent of diesel from classic American cars. We picked up our BMW 700s—fantastic, reliable machines perfect for this terrain—met our guides Juan, Siggi and our Cuban guide Ray and headed out.
Leaving the capital, we rode southeast toward Playa Larga. This area is steeped in Cold War history. We were riding straight into the Bay of Pigs (Bahía de Cochinos), the site of the failed 1961 US-backed invasion attempting to overthrow Castro’s new government. Today, it’s a tranquil spot with excellent beaches, offering our first taste of the Caribbean water.
Part 2: Colonial Jewels and Mountain Roads
From the coast, we turned inland and upward, hitting
some fantastic mountain roads in the Escambray range before descending into Trinidad.
Trinidad is a UNESCO World Heritage site and feels frozen in the mid-1800s. The wealth here was built on the brutal sugar trade of the 18th and 19th centuries. Navigating the bikes over the slick, centuries-old cobblestones was a technical challenge, but the city is stunning—a pastel-colored maze of colonial mansions and vibrant music venues.
Next, we moved further east to Remedios. One of the oldest settlements in Cuba, Remedios is often bypassed by tourists rushing to the nearby cays. It’s quieter, more authentic, and famously known for its “Parrandas”—one of the Caribbean’s wildest Christmas festivals. It was a peaceful stop that allowed us to see small-town Cuban life up close.
The Northern Coast Contrast
The ride from Remedios to Varadero offered the most jarring contrast of the trip. We moved from the struggling reality of rural Cuba into the polished, bizarre bubble of the all-inclusive resort peninsula. Varadero boasts some of the most spectacular beaches in the world—a seemingly endless stretch of white sand and turquoise water. It was a relaxing break, but it felt worlds away from the Cuba we had just experienced.
The Western Mountains and Tobacco Country
Leaving the resorts behind, we undertook a long ride west, skirting Havana and heading toward the province of Pinar del Río and the Viñales Valley.
The scenery here is dramatic. The landscape is dominated by mogotes—massive, steep-sided limestone karsts that rise abruptly from the flat valley floor. This is also the heart of Cuba’s famed tobacco country.
Visiting the Hemingway House was a great stop. We stopped at the famous house where Hemingway lived and wrote. They had left everything the way it was when he lived in the house and peaking through the windows gave a rare glimpse into a turbulent life of the world famous writer, father, husband, war hero and sailor.
We visited a traditional cigar farm, a highlight of the trip. Watching the farmers work the land using traditional methods (often oxen, due to fuel shortages for tractors) and learning the intricate process of curing and rolling tobacco gave me a profound appreciation for the craft. The food here, much of it farm-to-table out of necessity, was some of the best of the tour.
Finally, we pointed the BMWs east one last time, completing the loop back to Havana.
The Reality of the Road: Potholes and Perseverance
A motorcycle tour in Cuba is not for the faint of heart. While our BMWs were older but very well working and our guides expert navigators, the infrastructure is slowly crumbling.
The roads are a mixed bag. We experienced some beautiful, sweeping mountain tarmac, but large sections of the national highways are poorly maintained. You spend a lot of time slalom-riding around massive potholes, dodging horse-drawn carts, livestock, and broken-down 1950s Chevys. It keeps you alert, adding a layer of raw adventure that you don’t get on any other tours.
The Heart of Cuba: Its People
The scenery was beautiful, and the riding was thrilling, but the enduring memory of this two weeks is the people.
It is impossible to ignore the hardship. Cuba is currently facing severe economic distress. We saw some lines for fuel, some due to lack of internet, experienced the rolling electricity blackouts, and saw the ingenuity required to keep decades-old machinery running without spare parts due to the US embargo and internal economic failures.
Yet, despite poverty and shortages that would crush the spirit of many, the people we met were incredibly warm, welcoming, and proud. There is a palpable sense of community—a “we are in this together” mentality. Their resilience is humbling. They are a beautiful mix of happy people living in a very tough situation, and you get the distinct feeling that no matter what history throws at them next, they will prevail.
Conclusion
Two weeks on a motorcycle in Cuba is more than a vacation; it’s an education. It’s a challenging, exhilarating ride through a country that defies easy categorization. If you want smooth roads and reliable Wi-Fi, go elsewhere. But if you want amazing food, vibrant culture, challenging riding, and a connection with some of the most resourceful people on earth, join us on the next ride through this double sided paradise.
Till next time!! I will forever be changed by the experience of Cuba. It has shown me that everything is possible! There is no headwind strong enough to extinguish the human spirit!!
When you are ready:
For the eastern side of Cuba https://motodiscovery.com/tour/cuba-oriente/
For the western side of Cuba https://motodiscovery.com/tour/cuba-motorcycle-tour/
Keep an eye on our website for information of dates for this year. We will in addition, be adding an off-raod tour in Cuba
Great things to read on Cuba by our friend and the travel expert on all things Cuba, Christopher Baker:
Mi Moto Fidel: Motorcycling Through Castro’s Cuba and the Moon Cuba guide book—one of his five very detailed Cuban guidebooks.