Havana to the Hamptons

Well, that was quite a week!

Who would have thought, four days before #45 announced that he would be reinstating some of the travel restrictions to Cuba (which is when I purchased my ticket), this trip would be one of the most eye opening, humbling, and thought provoking experiences I’ve had in quite a while. The fact that just a day after my return to New York, I was driving through the affluent neighborhoods of the Hamptons to teach a class, was an incredible cultural juxtaposition. A week after being back, I’m still processing the experience on multiple levels. To make my thoughts more coherent, I will break down my insights/observations and recommendations into a few categories:

One of the exits at “Fabrica de Arte Cubano"

One of the exits at “Fabrica de Arte Cubano"



One of the biggest initial hurdles faced on this trip was letting go of some of my cultural norms (jaded New Yorker that I am) and allow people to talk to me and provide me with some insight into the Cuban culture, from their perspective. Being a country that, for a long-time, Americans have mostly received negative, propaganda based information about, it was startling how much fervor the Cubans have for their culture.


 One of the most rewarding interactions I had occurred by happenstance; after viewing the “Callejon de Hamel” cultural instillation,I was ready to move on to the next thing when my lady (bless her mid-western soul) said we should go back through one more time. When a gentleman who introduced himself as “Eddie” (pictured above) approached me to chat about the callejon, which is Spanish for “Alley,” I was about to use one of my normal NY leave-me-alone-isms (“I’m good fam”). But, thankfully, I did not. I opened my ears and mind to spend the next two hours with Eddie learning about the history of the callejon, Santeria and its Yoruba origins, and the refurbished materials that were used to create the artwork throughout the space, just to name a few topics. I thank Eddie for blessing me with such enriching conversation. It was a very humbling moment for me.

This experience will impact my level of interaction with waiters, cab drivers, or random people on the street, going forward. The Cubans I met were brimming with pride over their culture; that is not to say that they did not have concerns or disagreed with certain aspects of their experience living in quite unique a position, but the positivity that emanated from many of the people I spoke to was inspiring.

Callejon de Hamel, Havana, Cuba

Callejon de Hamel, Havana, Cuba



EVERYWHERE I went there was art. Everywhere. Whether in specific locations specially designated for artistic expression (“Callejon de Hamel”, “FusterLandia”, and “Fabrica de Arte Cubano”— which I all highly recommend), or simply walking down the streets and seeing it on walls, doors, or entire houses, the artistic expression and the theme of empowerment, cohesiveness and cultural appreciation, were all prominent throughout the artwork. As the adage goes, “a picture is worth a thousand words” and the tapestry that the Cuban people have created via their artistic expression is priceless. 



Cars are one of the most interesting aspects of Cuba (and yes, the last Fast and the Furious film was partially filmed there). They are old; many are holding on by threads, but the Cuban people drive those cars literally until the wheels fall off. One of the points of comparison between Havana and the Hamptons are the cars. The differences were startling, to say the least. But, ironically, at no point did I hear a complaint or feel like the Cubans felt negatively about their modes of transportation. To them, this is just what life is.

Some of the 1950s cars were nicer looking, and tended to be ridden by tourists, but the others were mostly used for two types of cab service; your regular taxi, and the “collectivo” taxis (like dollar vans, for my West Indian brethren), which for $1CUC you could travel along a specified route (with up to 6-7 other people, packed in one car) and be dropped off at various points of interest.  I know it doesn’t sound like the most appealing experience, but honestly, it was an amazing opportunity to engage in everyday conversation with the natives and I recommend at least trying it once while there.



Another stark contrast were the houses; that is not to say the houses in Cuba are not stunning (because they are) but for various reasons a lot of the homes were not maintained over the years, and now seemed like shells of their former grandeur. Architecturally they are still amazing to behold and quite a few of the best restaurants we went to were literally the front yard of someone’s home, or the top floor of a housing building. Again, the creativity and resourcefulness of the Cuban people was evident.  Mere days later, as I drove through the Hamptons, NY, one of the thoughts that came to my mind was that large houses need maintenance and for many of the Cubans who were given these large houses after the revolution, had received the property, but not the resources to maintain them. 



  • Stay at an AirBNB. Our host was amazing and made the trip so much easier
  • Learn a little Spanish (it goes a long way!)
  • Visit the above referenced art installations; they are truly breathtaking
  • Talk to the people
  • Budget how much money you will need for the trip - change your US cash to Euros and then to CUCs, once there. 
  • Eat the food Cuba is known for (i.e., Ropa Vieja, Maduros); the rest of the food is ok.
  • Embrace the culture! I repeat, EMBRACE THE CULTURE!