While sitting at the Devonshire (Shepherdstown) one fall evening, my friend Mo Amer expressed interest in visiting Cuba. I assumed he was joking. At the time, I wasn’t sure if Americans were able to visit Cuba legally, or if it was even safe to do so. Images of Fidel Castro in his military fatigues and ideas of a hardcore, censored state began playing in my mind. But after some research, I realized that Cuba has been a tourist destination for Europeans and Canadians for more than a decade, and was actually open to Americans.

I also read that Cuba was one of the safest Latin American countries, with few guns and a low crime rate. So, we logged onto Southwest.com and booked a round-trip ticket for $283. A couple weeks later, Mo’s cousin, Sam Kayed, booked as well.

Before we knew it, we were standing in the immigration line in Havana Airport. The immigration process went smoothly. After changing a little money, we picked from a line of vintage taxis waiting outside. When we arrived to our “casa particular,” which is a term used for rooms rented privately by Cubans to tourists, we truly felt like we had stepped back in time.

The cars were old, there were horse carts, and no street lights. The neighborhood was rather rough looking by Western standards, and Wifi was not accessible without purchasing a prepaid government card.

Photo ©Clay Anders

After checking in, we decided to walk to Havana Vieja, where most tourists stay. As we navigated our way through what seemed to be bombed-out streets, and bypassed catcalls from questionable looking women, the dilapidated buildings slowly turned into restaurants, mojito bars, and well-kept, turn-of-the-century architecture. We’d made it to Old Havana, and started to realize that Cuba is a great destination!

There’s quite a bit to do in Havana—with several beaches near the city requiring a short taxi or bus ride (which we never made it to). But we did mingle with locals on the Malecon, where the city meets the sea.

In the center of Old Havana, we saw great architecture, the capital building, and a large collection of pristine classic cars. Next, we explored El Morro and Castillo de San Carlos de la Cabañas, which are large forts along the bay. We also took the ferry across the bay and walked up to the best view in Havana—located near El Cristo de la Habana, a large statue of Jesus.

Additionally, we took a day-trip to Viñales, a rural farming region where mostly tobacco is grown. We took a tour through cigar plantations and a boat ride through caverns. Horseback rides through the valleys are also available. We highly recommend the Viñales for a two-day side trip if you like nature.

We also visited the old city of Trinidad—known as the “town of rainbow streets.” Trinidad is filled with ornate plazas and architecture, which has been unchanged since the 1850s. There, we had great piña coladas served right from the windows of private homes—and if you enjoy night life, there is a vibrant club located inside a cave near town.

Interacting with the Locals

In addition to sightseeing, we conversed with many Cubans throughout the trip. The locals were eager to chat, and were even more excited when they noticed I could speak Spanish. Several people told us about the low wages paid by the government. For example, a professor or a doctor may only earn $35-$45 a month, while the people who make big money are the hustlers that deal with tourists.

Waiters, bartenders, taxi drivers, Airbnb owners, and even people who cook or sling drinks from their porches can all make triple in a day the monthly salary of a doctor or lawyer. Moreover, several taxi drivers told me about the outrageous local values of their cars.

For example, a classic American car, like a ‘57 Chevy, goes for $40-50K. A driver of an old Soviet car that was all but held together with duct tape told me his car would sell for $16K, and newer economy cars cost $35-40K. When I told one driver how much cars cost in the states, he sighed and said “that’s so unfair.”

As advised, we refrained from bringing up politics with our Cuban acquaintances; however, several of them broached the subject. An elderly farmer in the rural Viñales valley told me that things were better in Cuba when Obama was in office. I asked him how the influence of our presidents could be felt so far from Havana, and he replied that everything trickles down. One of our favorite taxi drivers told us that if there was no U.S. trade embargo, everyone in Cuba would have plenty.

Photo ©Clay Anders

How to Get There

Although Cuba has much to see and plenty of friendly people, there is a slight issue in getting there. There has been travel restrictions on Cuba for years. Barack Obama eased travel restrictions a few years ago, which made obtaining a visa relatively easy. We simply booked a flight and then payed $50 online for our visa.

Southwest Airlines even provided us a link to complete our visa online. There are different visas depending on why you are traveling to Cuba. For example, the “People to People” visa and the “Support for Cuban People” visas are generally used for touristic reasons. We chose the “Journalist” visa.

Although we experienced a very easy travel experience to Cuba, there were some travel restrictions announced by President Trump on June 17 (2017) that may prohibit Americans from traveling independently to Cuba in coming months. A guided tour by a licensed and approved organization, such as Smithsonianjourneys.org, Insight Cuba, Cuba Explorer could assist you.

A cruise is another option that will not have been affected much by the restrictions. But if you are looking to avoid an organized tour, you can still attempt to obtain a “People to People” visa from the Treasury Department, though you may be denied.

Of course, you can take the route we took, and obtain a “Journalist” visa—and add to the knowledge base. We also encountered Americans who defied the visa process, and entered Cuba by flying in and out of a foreign airport. Keep in mind that this is illegal.

Cuba, at once both gritty and emerging, may not be the easiest destination to travel to in the coming months, but the hassle is certainly worth it. If you need refined amenities, such as Starbucks and constant Wifi, then you may be better served elsewhere. However, if you want to see a country emerging from a time warp, enjoy classic cars, historic architecture, and friendly locals, then you should seriously consider this engaging island just 103 miles from the southernmost tip of Florida.


— ARTICLE BY: Clay Anders (narrator), Mo Amer, and Sam Kayed.

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