Americans are just now dipping a toe here and there into tourism in Cuba, but the Canadians, Germans, and residents of other countries without a travel ban have been coming to Cuba for years. In 2014, the Obama administration set the wheels in motion to lift the 50-year travel ban for Americans traveling to Cuba and opened the floodgates for Americans to visit. There’s been some back and forth since then with the current administration, but Americans are traveling to Cuba in larger numbers than ever before. Which means it’s no longer unique to just check into a Havana hotel, rent a vintage Cadillac and sample cigars.

If you’re like me, you want a deeper travel experience, one that leaves you with memories and stories to tell for years to come. One that helps you understand the history of Cuba and the culture of the Cuban people.

Enter Ernesto Guevara. No, not Ernesto “Che” Guevara the Cuban revolutionary who was executed in Bolivia in 1967. I’m talking about his son, Ernesto, who was just two years old when his famous father was executed. Now in his 50s, Ernesto is taking Cuban tourism in a whole new direction with his company, La Poderosa Tours.

Poderosa means powerful, mighty, potent. It’s a fitting name for a motorcycle touring company, especially when you consider it’s the name Che gave the motorcycle which he used to travel around South America. You may have heard of the “Motorcycle Diaries?” Those adventures were taken with Poderosa the bike. Now, visitors to Cuba have a chance to create their own Motorcycle Diaries on a tour with Ernesto Guevara.

Ernesto has a lifelong passion for motorcycles, perhaps in homage to the father he never got to know. He is a lawyer by profession, but his passion is Harley Davidson's motorcycles. In addition to his vintage bike, he has built a fleet of Harley Davidson motorcycles with which to tour the island nation of Cuba.

I was fortunate to meet with Ernesto once, on one of my trips to Cuba. No questions regarding Che were permitted, so we had a more casual conversation largely about his motorcycle business. I found it fascinating that Ernesto was one of the early adopters to the budding entrepreneurial endeavors only recently permitted in Cuba.

A six-night, seven-day tour with La Poderosa covers nearly 600 miles over the course of six nights. Starting the moment you land, La Poderosa takes care of all the details. While you wait in a VIP lounge at the airport, all the paperwork is handled by their staff. Soon, you are off on a six-day circuit of the island. Enjoy authentic Cuban food and comfortable hotels every night, getting to know your guides and fellow passengers. This is no cruise-ship excursion, this is the real Cuba. Explore these cities and towns with expert guides who know Cuba, inside and out.

La Havana: Old Town Havana is a UNESCO World Heritage Site. Cuba’s capital city is full of Spanish Colonial architecture, craft markets, restaurants, hotels, and vintage cars. It’s the first point of entry for most Americans, and you’ll have two nights here before hitting the open road.

Cienfuegos: After leaving Havana, the first stop is Cienfuegos, also known as the Pearl of the South. Cienfuegos is on the south coast and known for colorful French Colonial architecture. It’s also a UNESCO World Heritage Site and has a gorgeous Malecon along the sea.

Trinidad: Another UNESCO World Heritage Site, known for outdoor adventures and nightlife. Trinidad is often touted as Cuba’s most beautiful city, and the architecture is indeed impressive. It’s also a great place for SCUBA diving, hiking to waterfalls, or enjoying live music and mojitos.

Santa Clara: Turning inland from the sea, the next stop is Santa Clara, which also happens to be Che Guevara’s final resting place. The Che Guevara Mausoleum and adjacent Museo Histórico de la Revolución are a big draw for travelers.

Varadero: Jutting out from the northern coast, and one of the closest points to Key West is Varadero, a place with white sandy beaches and turquoise waters of the Atlantic Ocean. Many of Cuba’s finer resorts are located here, as well as Dolphinarium, which is a stop on the Poderosa tour.

Matanzas: See the African side of Cuba with a quick stop in Matanzas, an often overlooked city on the north shore of Cuba. Only 90 kilometers from Cuba, this area was once a hub for sugar plantations, thanks to slave labor, hence the African influence.
If six nights is not enough, La Poderosa also offers a ten-day Cuba itinerary or you can customize your own tour to fit your preferences. The ten-day tour adds in stops at Pinal del Rio and the Vinales Valley, where world-famous Cuban cigars come from. You’ll also see the mountains of Las Terrazas, a Natural Park.

A motorcycle tour of Cuba with Ernesto Guevara is a once in a lifetime chance to experience Cuba with someone whose roots grow deep in Cuban soil.

Motorcycle Tours in Cuba: Experience Your Own Motorcycle Diaries