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  • Writer's pictureKevin and Roxanne

Cuba: 9-day trip back in time

Updated: Sep 20, 2020

Tragic Beauty. Cuba is a 1950’s time capsule.


Cuba has been on our bucket list before we even had a bucket list. A well-preserved 1950’s time warp, replete with warm weather, beautiful beaches, charming classic cars, wonderful people, fascinating history and very few American tourists, it perfectly aligns with our goals for an ideal travel destination. Throw in affordability and abundance of rum and heck yes! It’s a no-brainer.



A land of paradoxes, Cuba is beautiful and crumbling, resilient but still suffering.


Traveling in Cuba is safe, sometimes confusing, challenging, magical, and always rewarding (for us anyway). Before heading on our trip, we ran into people that loved Cuba and had returned yearly but also heard from people who weren't impressed. There is massive poverty, lack of basic supplies and people living in horrible conditions. It's not your typical Caribbean island get-a-way where you go to not-have-a care in the world. For us, it was a trip that required more research than usual, and through that process of planning, we became deeply curious about Cuban history, the Revolution and the complex relationship between the US and Cuba. For us, it was not only traveling to a beautiful location but experience and education that we are still processing.



A Complex History

Cuba was doing just fine with its own indigenous people until Christopher Columbus arrived on the scene and claimed the island for Spain in 1492, which eventually led to the extinction of the native population. Slaves from Africa were imported to work the tobacco and sugar crops, with slavery being abolished in 1886. Today, a significant portion of the Cuban population has African ancestry and the Afro-Cuban culture is very omnipresent. As one of our tobacco farm guides said, "We are all mixed and are a bit African, a bit Spanish, a bit of other - but we are all brothers and sisters."


After a brief occupation by Great Britain, Cuba was returned to Spain in exchange for Florida. The Spanish-American War, with help from Teddy Roosevelt and the Rough Riders on Cuban soil, resulted in Spain relinquishing control in 1898 and was followed by a 3-1/2 year US military rule. Cuba gained independence in 1902, with the US retaining a military base in Guantanamo Bay. What followed was years of economic growth and prosperity, partially fueled by American investments, including the American mafia. US-backed dictator Fulgencio Batista led the country down a path of corruption, with a widening gap between rich and poor, which eventually led to the Cuban Revolution, where Fidel Castro, Che Guevera, and supporters overthrew Batista and took control in 1959. The two-year revolution was deadly, resulting in tens of thousands killed. Businesses and property were seized by the Castro government and many of the wealthy fled to Florida. Given the US companies and individuals that had lost investments during the Revolution, the US severed ties in 1961. This explains the time warp and all the old American cars from the 50's. Russia propped up Cuba until 1991 until the USSR fell apart and afterward, Cuba fell into a 9-year long economic crisis which they ironically call "The Special Period".



In 2016, Obama started to normalize relations with Cuba, easing the restrictions on American travel there and loosening economic sanctions. It was shortlived, as Trump reversed most of Obama's progress, cutting off all cruise ships and limiting flights to only Havana. Trump's reversal of restrictions has led to great economic hardship, as the rest of the world followed suit and eliminated all cruise ships to Cuba. It's also led to confusion, in that many Americans don't even realize you can still legally travel there.



Hard-working, resilient and friendly Cubans

The Cuban people are resilient, warm, open, kind, generous and supportive of one another.

Some of our best experiences were simply our interactions with the Cuban people we met, such as our casa hosts, taxi drivers, and tour guides made our trip better and more interesting. And no, they don't need or want your American candy, clothing, trinkets or other American shit. Bring your time, energy and money to exchange with them for their services. That is the best way to help the Cuban people. One American couple we met brought a large suitcase with baseball catcher gear that they couldn't give away, as they weren't going to haul it with them everywhere they went. I had brought some Tootsie Pops, but was embarrassed when we thought about "strangers giving candy to kids". Just don't do it.


On the other hand, there are street hustlers to watch out for...

While there are very few beggars in Cuba you will see a few. I think we were approached by two. I gave them a few cucs, because, well, if we’re here to support the Cuban people a few dollars out of my pocket into theirs isn’t that big of a deal. There are, however, many jiniteros (street hustlers) hoping to get a few bucks out of you one way or the other. You will be approached often – many times a day, maybe several times within a few hundred feet, walking through the streets and near any plaza, museum, restaurant or tourist site. We avoided these overtures with a polite, but firm “No.” and by walking away.


Here’s a scenario: A man or woman will approach you, ask where you are from, where you are going and if you need help. They will likely say they have a cousin or friend in the USA – and will offer to help you in some way. They might even just walk alongside you and chat with you on your journey. They will then ask you for money for the “service”. If you pay them, they may go away, but may also continue to dog you, asking for drinks, a meal, etc. One easy response is to simply say “No, gracias” and keep walking. You can tell them you are going to meet some friends – you can use the names of your Airbnb or casa particular hosts. If they persist, you can be a little more firm and direct. Remember this - they may not have a job and are just trying to make a few bucks. Hustling tourists is an easy way to do that. You can be less of a target if you know where you are going, aren’t flashing money, jewelry, etc. You can also hire a guide ahead of time if you like.

  • There is no salsa festival. You do not need to buy tickets.

  • There is no special on milk.

  • There is no cigar festival. You do not need to buy tickets.

  • The 60-year-old guy trying to give you a few free pamphlets probably didn’t become a first-time father today, and probably doesn’t need $ to get to the hospital.


Afro-Cuban dance party at Callejon de Hamel on Sundays


Watch your Step

Havana is beautiful, old, elegant, raw and crumbling. Walking around any part of the city you can’t help but notice the contrast between pristinely restored historic buildings and the ragged decaying structures right next door. In fact, there is far more decay and antiquated infrastructure within the country than well-maintained buildings, roads, sidewalks and energy grids. This may not be as noticeable in touristy areas such as Old Havana, Viñales, Varadero, and the all-inclusive resort areas, but visit any number of other cities, take a stroll through less touristy neighborhoods or walk through central Havana even briefly and you will see the heartbreaking side of life in Cuba. Sewage in the streets, broken sidewalks, building rooftops caving in, people living in what basically amounts to a hole in a wall. It ain’t pretty folks. How has this happened? A few reasons. Communism isn’t what it’s cracked up to be. It may read well on paper as an idealogy, but 60 years of a communist dictatorship has not allowed the Cuban people to prosper. As more than one of our cab drivers explained to us – “No one really understands socialism or communism – but everyone understands that they don’t earn enough money and they don’t have enough to eat.” The US embargo/blockade (el bloqueo) on trade and tourism appears to have done more harm to the people of Cuba than to its government.



The Cuban government controls everything including how much time locals can interface with foreigners. The Cuban people have found clever ways to work in and around the systems in place. The average salary for a Cuban citizen is between $25 and $40 per month depending on one’s career. This is set by the government. Because of this, everyone has a side hustle or two. It’s not uncommon for doctors and mechanical engineers to drive a taxi (if they can afford to buy one) because they can make well over $100 per day. Tell me, what’s the incentive for a young person in Cuba to study to become an engineer or doctor when they can make more money as a cab driver?


Food is rationed and is scarce. There are few snacks in Cuba. Pop into a store – any store – and take a look at the few items on the mostly empty shelves. It’s fairly easy to find rum, but almost nothing else. Take a walk late at night or early in the morning and notice Cubans queuing for bread, rice, meat, vegetables, ration books in hand. Much of the food Cubans eat needs to be found on the black market. Just be aware of this when you consider complaining about your meal.



Observations and Thoughts

1. Cuba is a cash society. American credit cards or bank cash cards DO NOT work there. You have to plan ahead and have all the cash you need before you go. We have not traveled that way for more than 20 years and it took a bit more planning.


2. The internet is difficult and sometimes impossible to connect to. You have to rewind your brain back to the days of hard copy maps and plan out most things ahead of time. You can't rely on your phone or the internet. They may not work.


3. We spent 4 nights in Havana based in Vedado, 2 in Vinales and 2 more in Havana based in Old Havana (Habana Vieja). We intentionally limited what we were trying to see on this trip, so we could fully appreciate the things we did without being rushed. In all honesty, we could have easily fit in another city to visit.


4. Cuba is one of the most affordable places we have ever visited. It's a quick and easy flight from the US with many affordable options for lodging and food.


5. The food can be amazing, but also very mediocre with emphasis on quantity over quality at some places. Our privilege was showing through when we tired of rice and beans and searched out sandwiches.


Interested in other aspects of our trip to Cuba? Read about them here:


A view to crumbling Havana from the Malecon- the 5-mile long esplanade that follows the seawall along the coast.


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