Americans Should Manage Expectations on Havana

Unless you’ve been living under a rock for the past month or so, you’ve no doubt heard that the US is and will be curbing travel restrictions to Cuba and may soon end the trade embargo that has existed for 50+ years. I get asked constantly about Havana and Cuba in general. Everyone is so excited to go and I totally get it. However, I believe that most Americans have unrealistic thoughts and expectations about Cuba. I’m writing this post to help Americans realize that they need to manage expectations on Havana and Cuba. It may not necessarily be what you want it to be.
Lee Abbamonte, Havana, Old Havana, Cuba
I am the first person to state how happy I am that President Obama is finally trying to end the antiquated trade embargo. I applaud his courage to do this. It would have always had to be a second-term US President. I believe this should have happened long ago and while I totally understand the idea behind the embargo; in modern times it has outlived its usefulness.
flags, Havana, Cuba
The embargo and travel restrictions have, in my opinion, had the opposite effect of the original intentions. While the US didn’t want money flowing to the Castro regime, it was also contributing to oppressing the Cuban people by not allowing them to make money, be employed and essentially be exposed to Americans and tourists in general.
Old Havana, Cuba, Havana
Obviously, some people may disagree with my feelings on Cuba and the politics that go into it but that’s not the purpose of this post. The purpose is to help manage expectations on Havana itself for Americans that are so eager to go.
Old Havana, Cuba
First and foremost, all travel restrictions have not been lifted. So there is still some risk to going to Cuba via a third country but the likelihood of anything happening is very, very low. Tens of thousands of Americans a year have entered Cuba illegally for decades-including me.
Havana, Cuba, car
I went in August 2009 from the Cayman Islands and had no trouble whatsoever. It was as easy as any trip I’ve ever taken but was certainly a thrill at the time and I had a blast. I have since been back to Cuba for a memorable trip to Guantanamo Bay as well.
Havana, capital building, Cuba
Now people ask me all the time, what’s it like in Havana? People have an unrealistic sense of what it’s like and I hate to be a Debbie Downer but as I’ve said Americans need to manage expectations on Havana-so here goes.
Havana, diet soda
Havana is not this amazing place that’s been untouched by the civilized world. It’s not that. It’s a regular Latin American city with a lot of slums and a nice old city that is fun to visit but it won’t change your life and you won’t be discovering something that people have never been to. Tons of tourists come to Cuba, including Americans, although most western tourists are Europeans and Canadians.
car, Havana, Cuba
I feel as though the majority of Americans think it’s just a bunch of old cars and most Cubans have never seen the light of day. There are some old cars and some funky looking taxis-that is true. The buildings are also old and the majority are in major need of refurbishment.
Havana, Cuba, taxi
The Malecon is a nice area to walk around along the water and of course there is always sampling the local fare, cigars and of course, the rum. There is also the famous Tropicana show that every tourist who goes to Havana goes to and for good reason. It’s a lot of fun and cool to watch. It’s also not cheap and neither is much of Cuba, at least as of 6 years ago.
Malecon, Havana, Cuba
Havana really reminds me of Santo Domingo, Dominican Republic. Another city that’s OK but won’t be on anyone’s 30 best cities in the world list. So just keep that in mind when getting your head around Havana and Cuba in general.
Baseball field, Havana, Cuba
With Americans and the US influence coming into Cuba, there is no doubt there will be changes and hopefully for the better. The rest of Cuba is also much like the DR and the resort towns do have all-inclusive type resorts and of course there are several unspoiled areas and beaches. However, and again, please just manage expectations on Havana and Cuba in general.
Havana, Cuba
That said, go to Cuba and have fun and realize what you’re going to see and that way you’ll not be let down. You’ll see Cuba for what it is and hopes to become-not for what you want it to be.

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  1. Well said, Lee. I love Cuba and really enjoyed my time in Havana as well. However, after all of the questions. emails, and new articles over the past few weeks I think Americans really need to know what to expect. Cuba didn’t just open itself up to the world. Canadians and Europeans have been enjoying it just fine without us for years and thousands of Americans have been going illegally anyway. I’m excited more people have the opportunity to visit but they should manage their expectations like you said. Maybe skip Cuba and the DR and head to Haiti. All that Caribbean charm without the tourists! (and its 100% legal). Anyway, great article.

    • Clint, what’s up buddy?! Congrats on the Pats win and hope to see you in Arizona! I think Cuba is definitely worth visiting for sure but again, it’s just the expectations as I had back in 2009 when I went-it’d be hard to live up to those expectations. Haiti is an interesting place. I was there a week before the earthquake which is totally wild.

      • Thanks my man! Great to see the Pats back in the Super Bowl. I’m still looking into AZ. I went last time the Pats played there and lost the 18-0 game (we won’t discuss this…). I’d love to go back if I can work it out and secure a ticket but flight is ready to go. I am headed to the NYT Travel Show this weekend though so hope to see you there.

        I went to Haiti pre and post earthquake but it was bad before. Tourism is pretty dead but it has some really interesting sites and beautiful coasts. Cuba still has that charm I like even if it doesn’t meet our expectations of following Hemingway’s footsteps. I’ll definitely go back one of these days.

        Anyway, hope to see you this weekend and let’s go Pats!

  2. Thank you for being the one to finally say how it really is in Havana!

    I am so tired of hearing/reading all these articles in last few weeks about how amazing Havana is and how you must get there before it changes. It’s already changed. As you mentioned, hundreds of thousands of tourists go there each year-just not mainstream America.

    Havana is a reasonably pleasant place to visit for a few days but then move on.

  3. Very good post although I still really want to go to Havana. It’s good to hear this truthfully from someone who’s actually been there. Most media are writing from research as opposed to real experience and they don’t actually know. Good for you, Lee.

  4. Good, honest post Lee from your own first-hand experience…thanks.

  5. I am definitely one of the Americans you speak of Lee. I’ve always viewed it as an old fashioned car show where you take a step back in time. Thanks fgor clearing that up, it’s amazing how many view it that way.

  6. As someone who´s been living in Latin America for a while, I´m happy about the relaxed travel restrictions, and perhaps am less likely to hold strong misconceptions about Cuba. I want to go because I think Cuban salsa music is the best in world. (Less brass and more guitar than Colombian salsa) How did you find the music scene?

  7. Hey there, great write up. I am planning to go Havana from NYC (by way of Cancun) in Feb. I am not holding an American but I am on US visa. Do you know someone in my situation and have tips to share? My biggest concern is the stamping on my passport. Certainly don’t want to be blocked from entering US on my way back :/


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