Tour Cuba by Motorcycle with Christopher Baker

by Christopher Baker
tour cuba by motorcycle

Two decades ago I shipped my BMW R100GS motorcycle overnight from Key West to Cuba for a three-month-long, 7,000-mile exploration as a professional journalist. Come dawn, I leaned against the rail with the wind whipping my hair and watched Havana emerge from the sea. An imposing castle loomed over the harbor entrance, guarding the waters where great galleons had gathered, laden with treasure en-route to Spain. As we slipped into the harbor channel, I felt sensations of adventure and promise.

Only 90 miles separate Key West from Havana, yet in many ways the Florida Straits has been the widest moat in the world. While I spent the ensuing years savoring this remarkable country, Uncle Sam barred ordinary U.S. citizens from visiting Cuba. Then, in 2011, President Obama created a new educational license category to permit “people-to-people contact.” The licenses were issued solely to organizations—not individuals—for group travel. In April 2016, the “people-to-people” license was extended to individuals, effectively ending the travel ban.

tour cuba by motorcycle with Christopher Baker

Christopher P. Baker overtaking a 1950s classic American car, Cuba; copyright Christopher P Baker

Cuba, the Forbidden Fruit

Cuba has since become U.S. travelers’ destination du jour. In high season this year, the place was jam-packed with yanqui visitors making the most of the heretofore forbidden fruit. Cruise ships had finally descended, disgorging their hordes. And, sadly, the first spring-breakers had arrived to further diminish the “authentic” experience (and, no doubt, the Cuban culture).

The time to visit Cuba is now! And motorcycling is a great way to escape the swarm and serendipitously seek out a genuine Cuban experience.

Forget taking your own wheels, though. It’s still illegal under U.S. embargo laws for U.S. citizens to ship any vehicle to Cuba. And the only bikes to be rented in Cuba are flimsy scooters. But now every U.S. citizen can sign up for group motorcycle people-to-people programs, such as offered by Cross Cultural Journeys and RTW Moto Tours.

tour Cuba by motorcycle

Cannon-firing ceremony at Morro Castle, Santiago de Cuba; copyright Christopher P Baker

A Milestone Moto Tour

In January, 2013, I secured the first ever license authorizing such two-wheel “tours” of the island. I was so stoked, I couldn’t suppress my glee as fourteen eager motorcyclists flew south from Miami to ride a 2,000-mile counter-clockwise circuit from Havana to Baracoa, at the eastern tip of the island.

“Yeaahhhhhhh!” I couldn’t help but scream with delight at this first of many motorcycle tours I’ve since led around Cuba.

Tour Cuba By Motorcycle

Time-worn Baracoa was founded in 1511 as Cuba’s first city. Cusped within a bay spreadeagled beneath a huge flat-topped formation surrounded by rainforest, it resembles a mini Macondo, the surreal setting for Gabriel García Márquez’s novel One Hundred Years of Solitude.

tour cuba by motorcycle with Christopher Baker

Baracoa, Cuba; copyright Christopher P Baker

Arriving at Baracoa was its own adventure—a perfect tropical cocktail of adrenalin-charged curves, rugged terrain, and superlative vistas. Our trip in 2013 crescendoed east of Guantánamo, where we ran along a teal-blue Caribbean shore. At Cajobabo we turned north and clawed into the Sierra Cristal via a switchback—La Farola—so twisty it almost made me feel dizzy. The bike and I canted as one, arcing gracefully through the serried ranges and forbidding valleys. Ideal guerrilla territory! Every other turn offered a heart-stopping drop-off, with spectacular views over plains resembling Spanish mantillas.

Beyond the summit, the world fell away as the road spiraled down to Baracoa, hovering on the distant horizon beneath a brooding twilit fusion of rugged mountains and molten sky. As I pulled up to our hotel and hauled my motorcycle onto the side stand, I grinned broadly, knowing that my group could never have got so close to so much beauty inside a car.

“Congratulations!” I exclaimed to the group, which ranged from young Silicon Valley millionaires to adventure-seeker retirees that included two women. “You’ve just made history. You’re the first yanqui motorcycle group to explore Cuba end-to-end since the U.S. embargo was enacted in 1961.”

tour cuba by motorcycle

’We have and will have socialism’ billboard, Cuba; copyright Christopher P Baker

Juxtapositions Everywhere

Billboards reading “Patriotism or Death!” and “Long live socialism!” leave visitors no doubt that they’re in a Communist—or at least a Castroite—nation.” The enemy shall not pass our frontier!” screamed one billboard outside Guantánamo. And yet everywhere Americans go they are fêted.

It seems a strange juxtaposition. Rousing anti-imperialist murals offset by three generations of Cubans—most well-nourished, well-shod and clothed, and beaming benignly—sending reassuring waves to us Yanks. The considerate expression of a people uncommonly gracious and generous to a fault.

Che Guevara’s visage is everywhere, too. Motorcycling through Cuba you can’t get away from Che. I was once served a macchiato with his iconic image sprinkled in cinnamon atop the spume. The Guinness Book of Records claims the image of the bearded revolutionary wearing his beret with five-pointed star is the most replicated of any individual in the world. If so, half the images must be in Cuba, I mused as one of my groups photographed a billboard of a smiling Che and his famous phrase: “Hasta la victoria siempre” (Ever onward to victory).

tour Cuba by motorcycle

Motorcyclist with Che “Ever forward to victory” sign, Cuba; copyright Christopher P Baker

La Victoria…That’s the name, coincidentally, by which Cubans refer to the disastrously ill-conceived CIA-sponsored invasion at the Bay of Pigs. Arriving at the spot where socialism and capitalism squared off in 1961, it was difficult to imagine that blood and bullets had mingled with the sand and the surf here five decades before: Foreign tourists were sunning themselves on snow-white sands while Cuban families splashed about in the turquoise shallows.

Cuba’s Sheer Beauty

With all the hoopla about politics, it’s easy to overlook the sheer beauty of the place. The talcum beaches and chartreuse cane-fields. The emerald mountains and valleys full of dramatic formations. The ancient cities evocative of the once-mighty power of Spain. The whiff of cigar smoke and sea mist wafting over the Malecón as the sun sets and Havana succumbs to nights of sexy showgirls and sizzling salsa. Ah… the music! Everywhere, music hot enough to cook the pork.

Cars, Yes; and Motorcycles Too

Your first reaction of Havana is of having arrived at a 1950s Hollywood stage-set. Street after street is lined with astonishing—and mostly crumbling—Beaux Arts, Art Deco, and Modernist buildings. Cars from the Eisenhower era are everywhere, too, rumbling down the road to the rhythm of the rhumba on the radio. Chrome-laden DeSotos… Corpulent Buicks… Stylish Plymouth Furies and other relics of Mafia-era ostentation putter along beside sober Russian-made Ladas, Czech-made Jawas, and venerable 650cc Urals with sidecars. Suzuki 250s (imported by the Cuban state since the 1990s for use by security personnel and government officials) are ubiquitous, too, buzzing down every town’s dusty streets. And tránsitos—traffic cops—lurk roadside astride their Yamaha 250 Viragos and Moto-Guzzi 750s.

The BMWs, Suzuki V-Stroms, and Harleys that we ride seem totally out of place in this twilight zone country half-frozen in time.

tour cuba by motorcycle with Christopher Baker

Cross Cultural Journeys includes Suzuki V-Stroms on its 12-day ‘Motorcycle Diaries Redux’ itinerary; copyright Christopher P Baker

Wherever we stop, Cuban males coalesce to give us high fives and marvel at our exotic rides, which are imported from South America and Europe. “Phew!… hombre!” they exclaim. “What marque is this? How big is the engine?” And, inevitably, “How fast does it go?” You’d think we’d landed in flying saucers.

Every adventure motorcyclist knows that exchange. What differs in Cuba is that the people-to-people license requires a heavy daily dose of more formal off-the-bike “educational exchanges.” On trips that I lead, this could mean meeting my personal friends such as Cuban national team baseball player Alex Quintero, or world-renowned tobacco farmer Hirochi Robaina. Our routes are a magical mystery tour of such fascinating face-to-face encounters. And always you’ll meet harlistas—owners of Cuba’s few-score pre-revolutionary Harleys.

The Cuban Spirit—and Motorcycle Enthusiasm

Take my pal Luis Enrique González. He looks like a textbook harlista in his blood-red bandanna, chain-festooned jeans, and black T-shirt emblazoned with a Harley-Davidson logo.

He stomps down on the kick-start and the 1936 Knucklehead explodes into life. His blue-and-white antique Harley (one of twelve he owns) would be a museum piece elsewhere in the world. In Cuba it’s a daily ride. Yet keeping it running is a challenge in this land of U.S. embargo and perpetual shortage. “El cubano inventa,” he says laughing as he explains how Cuba’s proudly fanatical owners of yesteryear Harleys scavenge or monkey-wrench parts.

“What we can’t fix or cannibalize from cars we make ourselves,” Luis adds as our group gathers in his taller (workshop) in Havana’s once-tony Vedado district. “We tailor virtually any part you can think of, right here.”

Hecho en Cuba, chico!” he says as he displays handlebars and exhausts made from domestic piping. And drive chains that once powered conveyor-belts in Cuba’s Coca-Cola bottling plant. Russian GAZ jeep pistons substitute for Harley originals. And, he explains, in the grim years known as the “Special Period” after the collapse of the Soviet Union, lack of tires forced Luis to replace one of his Harley’s spoked wheels with solid 16-inch VW Beetle wheels.

Luis laughs, then grimaces. His fists clench, as if wrestling a bull, as he mimics trying to muscle the bike, with its flat tires, through a corner: “Coño! It was like being in a rodeo!”

Such colorful personalities embody the irresistible spirit and soul of this iconoclastic socialist isle in the sun.

tour Cuba by motorcycle

Quinceanera celebrating her fifteenth birthday, Trinidad, Cuba; copyright Christopher P Baker

Luis doubles as a Cuban road guide on some of my group motorcycle tours, alongside a compulsory Cuban tour guide who rides shotgun in a support van (to carry the luggage and spares). Together they add immeasurably to U.S. rider’s insights. Sharing my own knowledge and insights is second only to the thrill of riding: I, too, love helping clients peel back the layers. Understanding this enigmatic society isn’t easy. And that’s Cuba’s star appeal. It’s so close to the USA yet so utterly different.

On one recent trip, I led the group into the Plaza de la Revolución in Santa Clara. A granite monument of Che, portrayed mid-stride and toting a rifle on the scale of the Colossus of Rhodes, towers over the sprawling hilltop piazza. Che’s remains are interred beneath in a mausoleum open to view.

I lined up the group beside their bikes—on this trip BMW F650s and F800s and a sprinkling of Harleys—for a photo. Then for a lark—Cubans would never dream of the sacrilege!—one client pulled up his Harley Street Glide in front of Che. He gripped full-force on the brakes and wound up the Harley full throttle, as his teeth clenched tight on a stogie. I saw a military sentry in the distance go slack-jawed, unsure what to do, as the client eased out the clutch. Blue smoke enveloped him as the screaming mad rear tire burned rubber.

“Biker’s homage to Che!” he laughed.

“Er, I’m not sure my friend Ernesto, ‘Jr.,’ would approve!” I replied meekly.

Lasting Friendships

One day last June I was strolling along a cobbled street in Habana Vieja—Havana’s remarkable colonial core—when Che Guevara’s son bounded out of a bar and embraced me. Like his dad (in 1952 Che famously rode a 500cc Norton around South America), Ernesto is a motorcycle enthusiast. When I first met him about six years ago he was riding a jade-colored 1948 Harley-Davidson Flathead around the tumbledown streets. In June, after we dined together at a newly opened bar-restaurant—Chacón 162—in Cinco Esquinas, Havana’s trendy epicenter of sudden gentrification, Ernesto rode off on a 2015 Electra Glide Ultra Classic.

Suddenly I need a neck restraint to stop doing double-takes as locals burst out of their straight-jackets. Every third building in this overcrowded, once-sclerotic quarter of Habana Vieja is in the throes of a remake as a boutique B&B, hip restaurant, or—what’s this?—a gourmet heladería selling homemade gelato ice creams. All this thanks to economic liberalization initiated by Raúl Castro to promote private enterprise and kick the moribund Communist economy into gear. But nothing epitomizes the ‘New Cuba’ suddenly emerging before my eyes so much as Ernesto roaring off on his sleek new Harley tourer.

Motorcyclist photographer Che “Ever forward to victory” sign, Cuba; copyright Christopher P Baker

I often wonder “What does Ernesto make of it all?”

It’s pointless to ask. He never talks of his dad. He’s his own man. Although privileged, like most Cubans I know he’s humble yet self-assured. Cubans have grown up in a culture almost entirely devoid of materialism. Ostentation is alien to the Cuban way; to the concept of the ‘New Man’—someone embodying Revolutionary virtues, shunning individualism for the community good in the pursuit of egalitarianism. Che himself thought up el nuevo hombre before turning his back on Cuba in 1966 to lead a failed revolution in Bolivia.

Cuba’s material impoverishment hasn’t stifled the happiness and generosity of this disarming people. There are no Walmarts. No MacDonalds along the Malecón. Thankfully no advertisements imploring Cubans to Buy, Buy, Buy!

But that’s changing.

tour Cuba by motorcycle

Trinidad, Cuba; copyright Christopher P Baker

Cuba in Transition

Visitors today are witness to a decade of post-Fidel change as Cuba transitions to an uncertain future. Commercialism is taking hold thanks to a massive influx of cash courtesy the tourist boom and, last year, at least $3 billion sent from the USA as family remittances. Possibility hangs in the air like intoxicating aromas of añejo rum. And with it, I can already feel Cuba’s “innocence” seeping away.

Cuban youth increasingly seem wed, necks craned, to Samsung mobiles and iPhones. Everywhere reggaeton now assaults your senses, overpowering more romantic traditional Cuban tunes as you stroll the cobbled back streets of Habana Vieja. Dunhill (the English tobacco company) has sponsored advertisements promoting cigarettes—for God’s sake!—that in May 2017 sprouted throughout the nation. And riding a Suzuki V-Strom 1000 along the Malecón in August 2016 with a group of Chileans I was astounded when four young Cubans flew past on their own modern Japanese sports bikes.

Tour Cuba by Motorcycle: the Opportunity is Now

All the more reason to tour Cuba now I mused, reflecting on Ernesto having swapped out his beaten-about 1948 Harley-Davidson Flathead for a welcome-to-the-21st-century Electra Glide Ultra Classic.

Christopher P. Baker on BMW R1200GS at the Bay of Pigs, Cuba; copyright Christopher P Baker

For More:

Intrigued? Travel Cuba by motorcycle with Christopher Baker on one of his guided moto tours:

All photos by Christopher P. Baker, Copyright Christopher P Baker.
-Cover photo: Motorcyclists ascend La Farola en route to Baracoa, Cuba; copyright Christopher P Baker.

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Wilbur June 13, 2017 - 6:42 am

Fabulous article capturing the vibrant spirit of Cuba. I was there in January and loved every minute. Seeing by motorcycle rather than coach must be awesome!

Nancy Zaffaro June 13, 2017 - 7:35 am

Well, good for you for making the trip to Cuba, Wilbur, and so glad you enjoyed it. But I have to agree; traveling Cuba by motorcycle and the chance to tour with Christopher Baker, who knows the country so well, would be the best. Glad you enjoyed the article!

Anton May 1, 2018 - 11:31 am

Hi Chris, would you happen to have an address to a motorcycle repair shop in Cuba?

Christopher Baker May 4, 2018 - 9:30 am

Hi Anton… good to hear from you. It depends on the bike make. Most Cubans do their own repairs at home. But there are some master mechanics, mostly working on old Harleys or Soviet-era bikes


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