Last November, while trying to convince my husband that Iceland was an ideal winter destination and failing miserably, I stumbled across some cheap flights to Cuba. We really had no idea how feasible it was to travel to the once-forbidden country, but after some research, we discovered that we could legally travel if we considered ourselves to be one of 12 approved categories of travelers that is not "tourism." We traveled under the "support for the Cuban people" license, which as far as we could tell just meant we should not stay in government hotels or eat at government restaurants, activities we weren't really planning on anyway.
We bought our visas for $100 each in the Miami airport during our layover and were off! Although we had some concern about re-entering the country as well, we came back via global entry and didn't even speak to any customs official.
Our first stop, as I'm sure it is for the majority of people entering Cuba, was Havana. Cuba is a country that, similar to Egypt, I'd primarily describe as "interesting." It is completely devoid of advertisements. Food is sold in government stores that you have to wait in line to enter. All water and soda we came across was made by the same "brand." The food is, as you may have heard, almost universally terrible (although we found a few exceptions).
It is completely unlike anywhere else on the planet in a way that makes Havana seem somewhat empty and devoid of commercial activity. There just isn't a whole lot of business activity going on, although that is apparently slowly changing as regulations are being relaxed.
Where We Ate
Dona Eutimia. Probably the best place we ate in Havana. I made reservations at least a couple weeks in advance with an app called "A La Mesa." They charged a small fee to book a reservation, which I found slightly weird at the time, but we had no issues when we arrived at the restaurants, which is located in Old Havana. Delicious ropa vieja and fried pork. We paid about $20 for dinner for two people with drinks.
Helado'ro. Amazing ice cream in Old Havana which we just happened to find while wandering around. Far superior to the "ice cream" you can buy in the street which is apparently made without milk. Helado'ro serves milkshakes and affogato along with standard ice cream cones, which cost $1 CUC (equivalent to US$1) each. I had key lime pie and D had peanut butter -- both delicious.
Madrigal Bar. A very atmospheric bar in Vedado (the neighborhood we stayed in, west of Old Havana). It has a long list of imported liquors, a beautiful outdoor terrace and some really good tapas-style snacks. Good for a relaxing night.
Good to Know ...
Internet. There is no public WiFi in Cuba (at least not that we found). However, it is relatively easy to get online. You can buy an internet card at something called an ETECSA office, where for $1CUC/hour you get a card that has a scratch-off access card. You then have to go to a public area that has internet access (we happened to go to a public square in Vinales -- I'm fairly sure most public squares are internet hotspots). We didn't encounter any blocked sites and you can split your hour of usage across several sessions.
Taxis Colectivos. This is the cheapest and most confusing way to get around Havana. Basically, a lot of taxi drivers will drive back and forth along the same route all day, picking up 4-5 passengers and charging cents on the dollar to get across town -- basically like a faster bus. They are much cheaper than private taxis but can be difficult to find -- we had to ask around to find pick-up points and then ask each car that stopped where they were going. Might be difficult to use if you don't speak Spanish.
Casas Particulares. These are what the U.S. government wants you to stay in, and they're what we would have stayed in regardless. These are basically the same concept as AirBnBs and indeed we booked ours through AirBnB. They are popular all over Cuba and are basically homestays in Cuban households -- often a family renting out a room in their house, like where we stayed in Vinales. The casas we stayed at in Havana were larger and had more rooms, similar to an established bed and breakfast. They are considered a good way to get a glimpse into Cuban culture and apparently often have some of the best food in Cuba, although we did not eat many meals in our homestays.
Safety. Cuba is apparently one of the safest Latin countries, if not one of the safest in the world. Indeed, I saw no gated communities and no guns, both of which are common in other Latin countries I've traveled through, like Mexico or Colombia. Although the country is very poor, I am sure that lack of extreme income inequality has something to do with this. The literacy and education rates in Cuba are very high and we saw no homelessness on our visit. At no point did we feel unsafe in Cuba.