First a Bit on Travelling from the United States to Cuba
Getting into Cuba isn’t the most straight forward, especially for Americans. Under Barack Obama during his time in office as US President, travel to Cuba got much easier, although still technically not allowed. Prior to the loosening of restrictions, to get a visa you had to apply to qualify under one of 12 categories for permitted travel to Cuba, examples being Humanitarian, Educational, Support for the Cuban people, Journalism, etc. Nowadays you still have to claim you’re going for one of these categories once you’re at your departing airport in the USA, but it’s no longer enforced and no application process takes place ahead of time- more or less a nod from the US government to “go for it”.
The Department of State website it the best place to go for the lasted information. The website currently makes it sound harder to go than it really is. I personally went from Costa Rica but from my discussions from fellow Americans in Cuba who flew from the United States, I found they had no issues whatsoever. Those I befriended I know made it back safely to the USA as well. By far, “Support for the Cuban People” seems to be the most vague and ambiguous of all the categories and thus the most difficult for immigration authorities to argue against (which they wouldn’t under normal situations). This category was the choice of all Americans I met and I would encourage using this one. Although not always checked, you are supposed of having non-US health insurance during your time in Cuba as well.
I myself flew from Havana, Cuba to Tampa, Florida on Southwest Airlines to exit the country. Upon entry into the US and going through immigration, none of the officials thought twice about this planeful of cigar and rum loaded Americans coming back from Cuba and most, if not all of these passengers were obviously there for more tourist reasons than anything else. I didn’t even have questions asked. That little of a deal. Hope that puts you at ease.
*Under the new president, Donald Trump, things may change as he plans to take a different stance on Cuban-American relations. Any changes made may greatly affect travel from the USA to Cuba in the future. Again, see the Dept. of State site for more information.
Now from Costa Rica
Flying from other countries, such as Costa Rica, Canada, and Mexico has long been the “loophole” to get to Cuba for Americans. I just so happened to be in Costa Rica with friends before I would set out to Cuba on my own there-on. So regardless of most nationalities, Costa Rica can be a great jumping point from one beautiful place to the next.
There’s a limited few airlines that service this route. Copa, Interjet, Cubana, Avianca, Aeromexico, United, and American some of these. Cubana and Aeromexico must be searched on their sites as they aren’t included on those travel search engine sites. I personally found Cubana to be the best deal for a mere $137 one-way, but they have few flights- one a day if not at all on a particular day.
It’s Not a Trip Without Something Getting Changed Around On You
The flight from San José, Costa Rica to Havana, Cuba on Cubana Airlines (in Spanish: Cubana de Aviación) wasn’t the smoothest experience right off the bat. I got an email in Spanish about 36 hours before the flight that my 3:30pm flight was rescheduled to the morning and I must report to the desk by 7:30am. I had no idea when my actual flight was rescheduled to! I was lucky because not only did I have internet access, the email didn’t end up in my spam folder, and I was able to get there early. I was fortunately only in Tamarindo, a several hours shuttle ride to San José that was booked to arrive the night before anyways. So I was fine, but I couldn’t say the same to much of the other passengers since the plane turned out to be mostly vacant, presumably from this schedule bump.
To leave the country, an exit tax must be paid. Many airlines will include this in the cost of your ticket, so no need to worry about it if that’s the case. However, if you fly Cubana like myself, it is not included. If you are unsure if it is included, the exit tax desk has a list of the airlines. The tax is US$29 payable in US dollars, which is widely accepted in Costa Rica to begin with. If you don’t have enough cash, there is an ATM back out the nearest terminal doors and to the left at the departures passengers drop off area. You can practically see it out of the windows behind the exit tax desk.
After you have your exit tax ticket, you may proceed to the ticket counter. Here an employee asked if I had the exit tax paid. After my confirmation that I had, he asked, “Do you have your visa?” I wish he had followed that question with the word yet, as I got instantly nervous that I was supposed to already possess one. Like I mentioned, travel to the country is technically still not allowed for Americans, so I’ve been crossing my fingers during this entire transition from Costa Rica to Cuba.
Note that there are only tourist visas issued here, regardless of if you are American or otherwise. The whole category visa system doesn’t apply for travel initiating from Costa Rica.
Fortunately, I didn’t have any reason to be nervous as we then went to the counter where he pulled out a box full of empty visas. I paid the US$30 for the Tourist Visa (more cash you’ll need!) and he handed me one to fill out. From there, I got my boarding pass and I was off through the gates! Of which there was no line through security which was a welcomed surprise. By the way, don’t forget a Red Bull in your bag as you pass through the x-rays as they WILL find it and you’ll feel like an idiot.
From there on out it was normal boarding procedure and was soon enough off to Cuba!