Traveling to Cuba in 2018 for US Citizens is actually easier than one might think. I traveled to Cuba back in early 2017 under the regulations set by the Obama Administration. Unbeknownst to many, not much is different under the Trump Administration as far as traveling to Cuba goes. Travel for tourism, leisure, or recreational purposes is still prohibited for travelers with a U.S. passport. You can, however, travel to Cuba for other reasons. You must have a single entry travel visa to enter Cuba valid for a maximum 30-day stay.
As an American, you can travel to Cuba under 12 categories:
Official business of the U.S. government, foreign governments, and certain intergovernmental organizations
Professional research and professional meetings
Educational activities; including “people-to-people travel”
Public performances, clinics, workshops, athletic and other competitions, and exhibitions
Support for the Cuban people
Activities of private foundations or research or educational institutes
Exportation, importation, or transmission of information or informational materials
Certain authorized export transactions
How is Everyone Able to Travel to Cuba if It's Not Entirely Legal?
You know Americans have ways around everything. Remember the prohibition era? When we're told not to do something, we usually do the exact opposite by getting creative. Prior to the Obama Administration's approved exceptions of traveling to Cuba, many Americans traveled to Cuba through Mexico or Canada. Some still choose this route. Now, the most common visa that people travel to Cuba with is either the “people-to-people” category or the “Support for the Cuban people” category since you can you can loosely define what that is. Thankfully, you don't have to try that hard to be creative under either category. For example, staying at a local’s home, eating at a local family-owned restaurants, or signing up for a Cuban cigar factory tour can easily qualify as a people-to-people exchange or Support for the Cuban people - (just remember to save your receipts upon returning to the States in case the Feds ever want to check!).
Depending on your airline, you can obtain these visas by paying on the spot at the departure gate of your flight or paying for the visa over the phone in advance of your flight directly through your airline then picking up the physical paper visa at the gate. When ordering over the phone, it is okay if you initially choose one of the 12 reasons and then a select a different reason once you get there and put up the visa. For example, going there, I flew with Delta and paid the $50 over the phone with a Delta representative about a week before my flight, but when it was the day of my flight, I forgot which option I had chose,n so I ultimately checked off "people-to-people" once they distributed the visa forms at the departure gate. The visa is a piece of paper that you need to keep with you at all times. You can read more about the requirements here.
Traveling to Cuba legally under the “people-to-people” or “Support for the Cuban people” category
It is important for tourists to partake in local activities as much as possible. Not only does this give you a more authentic experience of Cuba but also contributes to Cubans quality of life. Staying in a local home, eating a locally-owned restaurants, and participating in local events in activities help Cubans make money on the side in their not-so-legal but common underground economy. Read more about this underground economy later in the post below.
Eat locally. In Cuba, there are two types of restaurants: government ran and family-owned. You can be sure that a restaurant is family-ran and family-owned when you see the word “paladar”. The food at these restaurants usually taste better, too.
Stay in a local’s home. Stay in a casa particular instead of chain hotels. Casas particulares are Airbnbs before Airbnb was a thing. This means a local rents out a private room in their home or their entire home. Casas particulares are a way for locals to get extra cash aside from their primary job. This is also a great way for tourists to connect with locals in a setting authentic to Cuban life.
Participate in local activities. Sign up for local activities, such as Airbnb experiences and tours. Airbnb now offers “experiences,” which can include a day activity for a few hours or a multi-day immersion. These experiences are a great way to get a unique experience and more authentic feel for life in Cuba by immersing yourself in the local culture. When I visited Cuba, I signed up for a 3-day salsa dancing immersion called La Salsera. I went out with local Cuban dancers, who were the Airbnb host’s friends and family and some of the most welcoming people that I have ever met. During the experience, I also met other Americans and learned history of casino/salsa. This is a great way to to meet people meet locals (both locals and other travelers) that share your similar interests. For other local activities, many people also go on a Cuban cigar factory tour where you can learn how they make cigars and even buy some to bring back.
One country, Two Currencies: CUP vs. CUC
"One country, two currencies" is one of Cuba's more peculiar idiosyncrasies. The Cuban peso (CUP) and the Cuban convertible peso (CUC) are both legal tender on the island, though neither is exchangeable in foreign markets. The CUC is pegged to the dollar and worth 25 times as much as the CUP.
As a tourist, you'll most likely use the CUC, which is the major legal currency of Cuba, the CUC. When you exchange your money in Cuba, you will get $1 for 1 CUC as it's pegged 1:1 to the US dollar. If you venture off into more rural / less touristy areas, you will use the CUP, which is about 1:30 (25 CUP for every 1 CUC).
Everyone Has a Side Hustle in Cuba
When you travel to Cuba, it is very common for your taxi driver to be a doctor, a lawyer, school teacher, or any other profession. That is because many actually make more money through their side hustles than their primary jobs.
In Cuba, there are two economies: one driven by the CUC and one driven by the CUP. As Cuba is a communist country, locals get paid their salary in CUP and have super cheap living expenses. However, to them it's not so cheap. For example, their monthly expenses could be: electricity bill $3, water bill $2, phone bill $2, rent $5, food $2 per month. Comparing these expenses to their total monthly salary of, say, $30, their total expenses might actually seem like a lot. Therefore, my taxi driver, who was a doctor by day and driver by night, chose to drive taxis since he was making far more money than he earned as a doctor. This is because he earned CUC, which essentially earns him US dollars while their "legal" Cuban job paid them in CUP. Every Cuban I met has a side hustle, which I considered to be the second economy of Cuba - more of an underground economy. Surprisingly, having this secondary job is not legal but everyone does it.
You can read more about my personal experience traveling to Cuba here.