Traveling to Cuba from the United States, is it difficult? Not really. Getting to Cuba from the US is easier than ever. Once you're there, the real challenges begin.
How to Get to Cuba from the United States
I flew from LAX to Havana, Cuba in January 2017. Alaska Airlines had just started a direct flight from Los Angeles. It was an exciting time. While in Cuba I watched the Trump Inauguration on TV. He would soon change the travel rules for Americans visiting Cuba.
Under the Obama-era rules, there were 12 categories of permissible travel to Cuba. I travelled under the "people-to-people" travel category. Beginning on June 16, 2017, individual travel to Cuba under the people-to-people category is no longer allowed.
Booking the flight to Cuba wasn't any different than booking any other international flight, other than the airline requiring me to choose my permissible travel category. At LAX there was a kiosk next to the ticketing booth where I could purchase a tourist visa (a requirement for entering Cuba). The tourist visa was $85 and sold by Cuba Travel Services.
How to Book a Hotel in Cuba
Credit cards issued through US banks don't work in Cuba. For a less expensive hotel, you can get by with just paying cash. For the most part, Cuba was much more of a cash-based society than the US.
For more expensive hotels where paying by cash might be less convenient, I found it hit and miss trying to pay for the rooms online prior to the trip. For example, I had no trouble booking Havana's historic Hotel Nacional online with my US credit card.
I was also able to book rooms at bed & breakfasts using AirBnB with no issues.
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