Invading the Land of Communism: Cuba

Let me let the cat out of the bag right off the bat: There are no communist countries in the world; they are all totalitarian dictatorships dressed in communist clothing. I mention this because it is good to keep this in the back of your mind so that when you go to these places you can see them for what they really are and not get caught up in the utopian mystique and romanticism of anti-capitalism (not that you won’t see the obvious poverty or that freedom is clearly not on the menu). Now we can move onto Havana and the raw sex appeal of this mysterious island.

Let me be clear from the beginning. As an American, you can go to Cuba. It is not the Cubans who are closing their doors to you, but rather, Uncle Sam.

Havana's Capital Building modeled after the US Capital

Is it technically illegal with huge penalties? Yes. Are they likely to grace your doorstep? No. With the Obama administration at the helm, many of the restrictions on Americans visiting Cuba due to the embargo have been lifted, however, they are mainly aimed at Cuban-Americans who charter flights from New York, LA, and Miami and require you to do the visa dance with the US State Department in Washington DC. By far the most common way, and the way that I took, was to catch a fight from outside the US (namely Mexico City, Cancun, or some cold icebox in Canada). They are daily and from Mexico range from $250-$500.

There is mystery, there is timelessness, and there is an essence to Cuba that is hard to explain. After visiting 80 something countries, I do not think I have encountered a country which left me feeling so emotionally and mentally perplexed. I like to get to the bottom of things and dissect them, but Cuba for me still by and large remains a land of paradoxes, yet one that is challenging, frustrating and interesting as I rack my brain trying to reach some type of reason for the way things are and how women can possibly exude so much raw sexual energy effortlessly.


Havana is basically a dilapidated Miami locked in time from 50 years ago. It has vibrant architecture comprised of colorful buildings and classic hotels that were once the place to be during the mobsters hay day. You can feel what it must have been like when sitting out on the verandas sipping mojitos listening to something Latin and sexy in the background. While most tourists and the companies that shepherd the tourists around aim the hordes toward the restored part of town, Havana Vieja, the real Cuba is just a side street away where the buildings are crumbling before your eyes. Here you can see people hanging out at all times of the day because hardly anyone is really fully employed since

Cuban man chilling with a Cigar

the only industries that Cuba has are Tobacco (cigars), Rum (delicious and cheap), and overt tourism (eerie and a bit sad), ergo there isn’t a whole lot of opportunity for the masses outside of fields related to the aforementioned group (besides prostitution). You can see kids playing baseball with sticks in the street as quad-cycle taxi pass you by pestering you for a ride as well as old men puffing cigars while – walking, talking, doing work, making food, playing with children, driving cars, riding bicycles – pretty much they are smoking if they are still able to breath.


In a nutshell, Cuban food is terrible. And by terrible I mean you will kiss the ground when you de-board the plane to your homeland and never speak ill of Chilis again. You will see tons of little windows of people’s houses on the side street selling real Cuban food to real Cubans. It is cheap and the taste reflects this. The menu ranges from pizza (white bread with paste-like tomato sauce), to bread with mayonnaise (seriously), and other small items that are barely edible (with the exception of maybe an egg sandwich). For a general idea of the costs if you eat like a local, a piece of pizza (which for many Cubans would be considered a luxurious (and unhealthy) treat) costs between 6-20 national pesos – about $0.25-$0.80 USD. Cuba has two currencies, a local currency referred to as nationals or pesos (24 national pesos per $1 USD), and Cuc (pronounced cook and is equal to $1). While you get a lot more bang for buck with the local currency, you can’t really buy anything you really want with it  (everything in the sin category) except indiscernible street food and the occasional collectivo (group taxi).

Jackpot - Coconut Ice cream inside a Coconut

Occasionally, and I stress occasionally, you can stumbled upon something delicious in the food category, like coconut ice cream, but it is more of a lunar eclipse than a beautiful sunset statistic. While this food is bad both in terms of health and its horrendous flavor, it is not the local faire that will be generally sold to you. You will be offered pork (most popular on the island), fish, shrimp and lobster at restaurants and many places will do the full spread with a mojito thrown in for $10.

My first of 13 Lobster & Mojitos Meals in Cuba - Excited

However, while at first you will be elated for getting lobster at such a bargain price, after awhile you will lose much to all your initial enthusiasm. I found that the Cubans do not know how to cook seafood (always overcooked), namely because they don’t eat it themselves. There are laws against it (some break it – land of paradoxes) while other types of food, namely beef is forbidden for them because it cannot be sustained on the island (missing the free market yet?). I wish I could relay a hard and fast rule of what can be eaten by locals or not, but the rules are murky and the people themselves seem to have varying levels of understanding and obedience to the law.

Struggling on 9 of 13 Rubber Lobsters

Like most “communist” states, the people are usually so impoverished that it is somewhat socially acceptable to steal from the factory or break some rules in an entrepreneurial hustle. The Mojito, a delicious concoction of sugarcane, mint and rum is the national drink.

Cubans buying bootleg Rum

It does however taste different than what you have been served in your homeland as it is not muddled and heavier on the rum side. Prices range from $2-4.50 with most falling in the $3 range, unless you get suckered by a smooth talking local into buying him a mojito that costs $5 (with a $2.50 kick back to him). Beer can be had from $1 to $3 with most falling in the $1.50 department, however, should you wish to hustle your way to drinks with your meal, any cocktail made with rum will more willing be doled out as rum is cheaper than water practically ($4-6 for the sweet nectar of the Caribbean).


Basically in Cuba you have two choices – hotels and Casa Particulars. You cannot stay with locals unless they have special permission from the government to host you (does socialism still sound sexy?) so any ideas of bunking up with locals ( or staying with anyone that you are friends with is out of the question. The hotel quality ranges as some are old hotels built by the mobsters,

Hotel National in Cuba - Mobsters & Frank Sinatra

which still are pretty old and run down while others are of the high-end variety which have all the amenities you would see in other Western hotels (minus high-speed internet and employee’s who put on a fake smile) along with the Western price tags. The other option, and also the most interesting, is to stay in Casa Particulars, which are the homes of Cubans who have a special license from the government. Here you can stay with local families in your own room (or one with 2-3 beds) from anywhere between $15-$45 a night for the whole room (so quite economical for 2+ people). The hosts usually offer, and by offer I mean pester you mercilessly, to buy their food. The thing about Casa Particulars is that the hosts’ pay the government tax per room rented out each month regardless of occupancy and have to pay for the privilege of offering guests food, also regardless of you buying it. Thus, there is an urgency to get guests to stay at their Casa and at the same time, a subtle to overt pressure to buy food from your hosts. If you are staying for a week, it is not problem, as the food that the Casas’ serve is usually better than at restaurants (moderately overcooked vs rubberized), but if you are there for a longer duration (3+ weeks in my case) it can get annoying rather quickly as you don’t always want to eat the same food as mentioned above night after night. They all sell the same food and it is roughly the same quality and the same price (surprise – it’s all the same comrade). One week it will be fine, at three weeks you may even daydream of the Olive Garden.

But hey, there are also classic cars, live music, sensual dirty dancing and sex in the air – to be continued…

Turner barr

Hi, my name is Turner. I travel the world, hustle to find interesting jobs, and write about what happens when you read too many self-help books.

  • Anna
    Posted at 16:59h, 29 May

    Great post Turner… loved it !!! 🙂

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    Posted at 14:47h, 16 January

    Yeah you most definitely don’t go to Cuba for “la comida”!

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  • Bob
    Posted at 00:02h, 23 February

    Hey man, I’m planning on heading to Cuba in March, and I was curious about how you sorted your flights. I was planning on flying into Cancun and then flying to Havana, but since I’m also an American I cant purchase my flight from Cancun to Cuba in advance. I was hoping you might provide some insight in how to deal with this?

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      Posted at 01:39h, 23 February

      hey Bob. I actually had a different situation as I flew standby. But from my understanding is that you buy a ticket with cash from a travel agent in Mexico.  Check out aircubano. Or this article for more info. Also, you will want to bring cash, I recommend bringing Mexican Pesos, or Euros as the US dollar has an addition 10% fee attached to exchanging it. You might also look into getting preloaded visa cards with cash, but to take out the hassle, cash is king.