I started writing this before the 2016 Debacle (I mean election) and the death of Fidel Castro. It's unclear what the future holds for U.S./Cuban relations and what travel for U.S. citizens will be like. One can only hope that things will get easier (and perhaps normal?). But truthfully, under Trump, I wouldn't hold my breath. All information presented pertains to how U.S./Cuban relations stood as of November 2016.
So you want to go to Cuba? You've researched and haven't found any truly great information? I'm here to change that.
A restored classic car driving down the Malecón in La Habana
In planning for my trip to Cuba I read blogs, news articles, bought the guidebooks and poured over Trip Advisor. I found a lot of itineraries and interesting things to do once in Cuba, but nothing comprehensive on how to physically get into the country or navigate it once there. Also, the complaints on Trip Advisor were laughable, many people clearly didn't understand or have any expectation of traveling to a Communist, developing country.
Disclaimer: I do not speak Spanish. While it's not impossible to travel in Cuba speaking no Spanish, it will be infinitely beneficial to your experience if you do. I had many great experiences during my two weeks in Cuba but I do not kid myself for a minute that most of it was not part of the well established Gringo Trail there.
Getting there
At this time there are 10 airlines that have either announced flight schedules or plan to announce flight schedules to Cuba from the United States. There are only 20 flights daily allowed to fly from the U.S. to Cuba and a majority of these will originate from Florida. For more detailed information check out this Travel + Leisure article.
At the time my boyfriend and I bought our airfare there were no flights scheduled from the U.S. so we flew through Cancun, Mexico. Buying airfare online was easy. I booked our roundtrip flights from Salt Lake City International to Cancun and then purchased roundtrip flights from Cancun to Havana separately. When traveling there again I will probably just price compare as we will most likely have to take the same amount of connecting flights to keep costs down. Our itinerary was:
Thurs 10/20, JetBlue SLC to MCO #802 depart 10:46 p.m. arrive 5 a.m.
Fri 10/21, JetBlue MCO to CUN #1713 depart 7:45 a.m. arrive 8:38 a.m.
Fri 10/21, AeroMexico CUN to HAV #447 depart 11:09 a.m. arrive 1:20 p.m.
Thurs 11/3, AeroMexico HAV to CUN #448 depart 3:15 p.m. arrive 3:38 p.m.
Fri 11/4, JetBlue CUN to JFK #752 depart 11:08 a.m. arrive 3:49 p.m.
Fri 11/4, JetBlue JFK to SLC #71 depart 7:44 p.m. arrive 11:08 p.m.
When I admitted to the AeroMexico site that I was an American, it merely prompted me to choose one of the 12 authorized categories of travel. I selected "Journalism," as I knew I would be blogging and photographing. The only hiccup was that my bank thought the charge was fraudulent and I had to call and confirm it was not. My payment processed and we were set!
If you do plan to travel direct from the U.S. you will still have to fall under one of the 12 categories. However, they are broad enough that anyone could make something work. These have always been the accepted categories of travel, the change is that you no longer need to obtain official permission to visit, but rather just fall into one. From research it seems like the days of the government prosecuting you for traveling to Cuba are over. And if anyone were to ask I would simply let them know that I am just as American as Beyoncé.
Keep in mind that you will still need to buy a tourist card for entry into Cuba. If flying from the U.S., the airlines will offer this to you. If flying through a gateway country, you can purchase them at the airport. We bought ours in Terminal 3 of the Cancún airport at the AeroMexico help desk (not the check in desk). Make sure to have cash on hand for this. The desk accepts U.S. and we paid $20 each.
Cuban Tourist Card
Our flights to and from Havana were not full. I suppose you could show up day of and buy your airfare, but as a planner, and since it's unnecessary, I liked the security of knowing I would be getting to Havana.
Entering the country
Immigration through Cuba was no different than any other country I have been to. Cuba is so used to Americans coming that they will offer to stamp your tourist card instead of your passport. I had to ask for them to stamp mine, I wanted the souvenir and I have Global Entry. Although, from all of my research, everything we were doing was perfectly legal. (Update: I renewed my passport by mail after returning from this trip and had no problems. I say go for the stamp!)
Be prepared to wait in a HUGE blob of people after getting stamped through. Everyone must pass through a metal detector and have their carry-ons re-scanned. There was no rhyme or reason to how people were lining up, mainly because there didn't seem to be an actual line. I estimate it took us at least an hour to get through the blob. And this inspired our theme of the trip, "That's Cuba."
Money
Travel to Cuba may be easier for Americans, but the United States still has the embargo against Cuba in place, which prohibits trade and exchange of economic activity. For American travelers this means that you will not have access to your bank or credit cards, and will need to bring enough cash to cover you're trip. There are a lot of rumors out there that this will change but I wouldn't hold my breath. However, Stonegate Bank based in Florida announced that they are offering a MasterCard that is supposed to work in Cuba. Of course I found this two days before leaving, so that was off the table for my trip.
There are two currencies in Cuba, the Convertible Peso (CUC) and the Cuban Peso or moneda nacional (CUP). The CUC to US Dollar is always 1:1, the government dictates this. For every 1 CUC you would get 24 CUP. The CUC is often referred to as the tourist currency, and the CUP as the local currency. Not speaking Spanish really hinders your ability in using CUP often, we mostly dealt in CUC.
CUP on top, CUC below.
Another fun money fact, there is an automatic 10% penalty for converting U.S. Dollars to CUC in addition to the 3% financial transaction charge. So that means no matter what, for every 100 U.S. Dollars you convert, the best you can do is get 87 CUC back. It is suggested to bring Euros, Mexican Pesos, Canadian Dollars or British Pounds instead to avoid that extra 10%. We went with Euros.
We exchanged 20 CUC to CUP on the advice on many of the blogs I had read. However, it became more of a hassle during our trip to figure out where to spend them than anything. On our last days in Havana we got the hang of it, as more restaurants and shops had prices listed in both, and there was more street food there. I am confident that if one of us spoke Spanish we would have been able to spend more CUPs than we did. However, it's hard to bargain with someone when you're not fluent in their language and they know you're not a local.
Since coming back I came across this blog which outlines true budget travel in Cuba. We did watch what we were spending, but that wasn't the focus of the trip. Traveling in Cuba is definitely cheaper as a couple or group than solo. You can split rooming and travel costs easier than if you're just one person.
You can exchange money at banks, a cadeca (Casa de Cambio) or major hotels. Try not to exchange money at hotels as the rate will be way worse. But in an emergency situation it's a good fallback. As long as you have your passport with you, aren't trying to exchange money at 12:30 p.m. and are willing to wait in line, exchanging money is pretty easy. Note that banks and cadecas close at 12:30 p.m. for a lunch break. No matter how long the line outside of it is. Pay attention to banking and cadeca hours (these are easily found posted on their doors). During our trip we tried to have enough money for the next 3 days available. We didn't exchange all of our money at once in order to conserve Euros.
Line for the Cadeca in Plaza San Francisco, Havana
Internet
This blog does a great job detailing how to connect to WiFi in Cuba. Although it's possible to connect to the internet in Cuba, we didn't bother. We took it as a break from social media, and with the election getting down to the wire, it was extremely welcome. Matt has a DeLorme inReach SE, so we were still able to let our moms know we were alive and well.
Helpful technology
Without internet it can be hard to navigate a foreign place. Before leaving I downloaded the Cuba Galileo Offline Map. This app was essential for navigating without having to open a guidebook. You can drop pins and save pre-loaded places and with the bearing line, find your way easily to where you want to go. This app worked all over, in Havana, Trinidad and Viñales.
As a non-Spanish speaker, I highly recommend downloading Google Translate's offline Spanish library. I grew up in Southern California so I have a little Spanish under my belt (I opted for French in school). And when traveling to a Spanish speaking locale, I usually can get by with the basic words and phrases I know. But the app allowed me to access vocabulary I didn't know I needed until I did. Also, hand talking becomes very useful.
Good reads
In an effort to not act like a Kardashian while in Cuba, I turned to some recommended reading:
I also brushed up on basic Cuban history. However, I did not engage any Cubans in political discussions. I felt that both my Spanish and Cuban historical knowledge were too poor for me to carry on a meaningful conversation. I also did not want to presume anything or get anyone in trouble. (Cubans are still suspicious of speaking poorly of their government for fear of retribution).
For more reading check out The New York Times' list.