Riding in Cuba: Revolution, Raki, and Rum

In 1996, I cruised to Cuba at night like smuggled human freight in Ernest Hemingway’s To Have and Have Not.

“Okay, vee go now,” said Rolf, a feisty Swede, tossing me two thick bungee cords to lash my BMW R 100 GS PD to the rail. “Be quick. Vee go!”

Rolf was already easing away from the dock in Key West while I was still tethering the bike as we slipped past the Coast Guard station. He’d just been cleared for departure to Cuba as a holder of a rare license to transport “humanitarian aid.” Rolf had agreed to let me slip aboard for the price of his fuel.

“Get out of sight!” Rolf cried. “Get below for God’s sake!” Beyond the harbor mouth, the Gulf Stream was in tormented flood. The Jevericka began to pitch and roll wildly.

It’s been 25 years since I rode my bike more than 7,000 miles around Cuba as a licensed professional journalist. The panache of touring Castro’s Cuba by moto turned my work—researching the island from end to end for my Moon Cuba handbook—into a fantastic adventure.

Just getting the bike to Cuba proved the hardest undertaking of all. I’d found Rolf by sheer fluke. Direct shipment from the U.S. was out of the question due to the embargo laws. It’s also illegal for a U.S. citizen to ship a vehicle to Cuba from anywhere in the world: they’re considered an “export,” however temporary the period of intended stay. In any event, the cost of flying a bike in from Canada or Mexico was prohibitive. Nor did Cuba have formal motorcycle rentals back then. When five-time RTW motorcyclist Dr. Gregory Frazier wanted to ride around Cuba two decades ago, he eventually flew in and negotiated private deals to rent two rusting Soviet-era models—a 1972 650cc “run around,” and a 1980 350cc Jupiter.

Motorcycle & Gear

2018 BMW F 700 GS

Helmet: Nolan N70-2 GT Hi-Vis Fluo Yellow
Jacket & Pants: BMW Airshell
Boots: Forma Adventure
Gloves: REV’IT! Dirt 2

Thanks to President Obama’s loosening of travel restrictions on Cuba, in 2013 I initiated and led the first U.S. group motorcycle tours of Cuba since the Revolution. I’ve since ridden in Cuba on various BMW and Harley-Davidson models and, in 2016, even a Suzuki V-Strom 1000.

So, let’s fast forward two decades to my last motorcycle tour on the island.

Tobacco Roads

I’m thrilled to be back in the saddle, retracing my journey through a country I’ve grown to know well and love dearly. I’m leading a BMW Rider Academy of Turkey tour group. Our rides are late model BMW F 800 GSs and R 1250 GSs, plus a Harley-Davidson Road King, shipped in from Europe by Edelweiss Bike Travel (the company has also arranged a support van and driver to carry our gear). They seem totally out of place in this Twilight Zone country half-frozen in time.