Why I’m Changing My Mind On Traveling To Cuba

Filed Under: Travel

Over the past few months we’ve seen the major US airlines begin selling tickets for flights to Cuba. It’s no surprise that so many US carriers requested rights to operate routes to Cuba, given that it’s the first time in decades that such flights are possible.

However, I also think we’re going from one extreme to the other. While there’s certainly interest among Americans in visiting Cuba, the actual demand isn’t there, at least not to fill the thousands of seats per day now operating between the US and Cuba.

Major airlines recently had their third quarter earnings calls, and on them we heard several airline executives say that flights to Cuba are an investment in the future, and that they won’t be making money anytime soon. Now, I suspect flights between South Florida and Cuba could be profitable pretty quickly, but that’s simply because they’re ~200 mile flights.

But any of the longer flights will be much more challenging to turn a profit on.

Why I haven’t been rushing to travel to Cuba

Since news of the embargo being lifted was initially announced, I think I’ve been more indifferent than most when it comes to traveling to Cuba. So many people seemed to say “OMG I need to go ASAP before it gets too commercialized.”

However, I think the reality is that it’s going to be many years before we see major changes to the infrastructure.

So don’t get me wrong, Cuba is certainly on my list of places to visit, though I haven’t been in any rush to go, and figured I’d travel there in a few years. While I’d like to go to Cuba before there are dozens and dozens of new mega hotels, at the same time I wouldn’t mind waiting until credit cards are accepted, things are better organized, etc.

Besides, there’s a big rush of people looking to go right now, which has been driving up prices of the very limited hotel capacity in the short term.

Why I’m changing my mind about visiting Cuba

In a way I think I’ve been looking at visiting Cuba wrong. I was thinking to myself that when I visit Cuba I wanted to make a big trip of it, explore several cities, etc. That was partly because the cost of flights has been ridiculous, at least when they were first announced. When American started selling tickets to Cuba they cost ~$450 from Miami, which is about a dollar per mile.


However, as more airlines have added capacity, prices have dropped and dropped and dropped.

Early yesterday I happened to see how cheap JetBlue’s flights were between Fort Lauderdale and Havana. Roundtrip tickets are going for just ~$135, which is incredible.

The deal is even more lucrative if redeeming TrueBlue points. You can fly roundtrip from Fort Lauderdale to Havana for 2,600 points plus ~$48 in taxes. That’s like getting over three cents per TrueBlue point, which is more than double their usual value.

jetblue-havana-3 jetblue-havana-4

So what’s really changing is that I’m viewing a trip to Cuba differently. In the past I thought a trip to Cuba needed to be a big production, and I just didn’t have the time in my schedule for it.

In December I’ll be in South Florida anyway, so given the above fares I figure I might as well take a quick weekend trip to Havana. There’s even a Four Points by Sheraton Havana, where I could either redeem points or book a paid rate and earn points (given the number of points required, paying cash seems like the best option). Major hotels in Cuba are still very expensive, given how little capacity there is.


Bottom line

While I don’t think Cuba will change overnight, there’s no reason not to visit with how cheap the airfare there is. While I hope to explore Cuba more in-depth in the future, a quick side-trip to Havana is perfectly practical thanks to the super cheap fares we’re now seeing.

Anyone else tempted to visit Cuba thanks to all the low fares? Has anyone been yet, and if so, how was your experience?

  1. Seeing the title made me think you might have finally developed a conscience. I thought maybe you decided not to support oppressive, anti-American regimes like Cuba. Maybe it would have even led to you to question your support of gulf carriers owned/operated by oppressive, anti-Gay, anti-non Muslim, anti-American regimes. You might have also begun to question whether your extensive airplane travel is hypocritical given your (likely) political party’s demonization of fossil fuels. But alas, I was mistaken. Nevermind.

  2. “I might as well take a quick weekend trip to Havana”

    Which one of the 12 tourist licenses will you be using?

  3. I’m very much in two minds too. I agree that you wouldn’t want to wait 5 years when its full of package holiday makers from the US and people treat it like Cancun and there’s no culture at all but I’m also hesitant to go somewhere that doesn’t know (or care) what tourists need and want.
    As an Australian, we’ve always been able to visit, and while it’s been expensive, it’s been doable via Mexico or Canada. But friends who went recently said its not an easy place to visit at all. The infrastructure isn’t there and they said every day it was just a struggle – not a holiday at all. Very difficult to get money, terrible food, locals don’t speak English and speak a really dirty Spanish that Spanish speakers can’t even understand. They said it wasn’t really worth the (considerable) effort.

  4. Just a point of clarification. The Embargo has not been lifted. The administration has eased restrictions on travel and commerce with Cuba. But until Congress acts, the Embargo remains.

  5. I just got back from a week stay in Cuba and for me it was FASCINATING. Yes, things are more complicated but nothing that cannot be managed, just make sure you take cash and thats it. Travelling to Cuba with a different mindset is a must. I would not recommend the Four Points as it is really far away from old Havana, instead, I would recommend the Saratoga Hotel where Madonna stayed, presumably the best hotel in they city.

    Note about Cuba: Food is pretty much horrible, don’t go with any expectations.

    WR: get a life.

  6. @ Ben — More or less matches what I’ve heard. I can’t imagine coming from the other side of the world to visit under those conditions, but for an hour flight it seems worth the visit to me.

  7. You still need to go on a People to People license or another exception. Most any competent travel agent could assist you but you can’t just book a flight and show up. Wanted to mention that so readers don’t get the wrong idea. Last time I went to Cuba was 15 years ago, curious how things have changed.

  8. DO NOT STAY AT HOTELS IN CUBA – casa particulares, which can be booked on AirBnB are the way to go – they start at $18 a night and are usually pretty nice and come with breakfast!

  9. “Very difficult to get money, terrible food, locals don’t speak English and speak a really dirty Spanish that Spanish speakers can’t even understand. They said it wasn’t really worth the (considerable) effort.”

    Good grief. If you travel expecting everywhere to provide you with exactly the same sanitised, corporate-branded, up-market experience as you get everywhere else in your world, just what on earth is the point of you leaving home?

    Cuba is an extraordinary place, quite unlike anywhere else on earth. It’s a police state – but then, poor black people in many US inner cities might recognise that experience. And no-one on here seems to have any qualms about travelling to slave states in the Middle East. Cuba has an extraordinary built heritage from conquistador-era towns to Modernist architecture. It is not renowned for its food, but you can still eat well here. And the people I have encountered on trips spanning thirty years have been pretty uniformly friendly and welcoming.

    Cuba is anti-American? I hate to break it to you, but so is much of the rest of the world. And isn’t travel supposed to help us break down irrational differences and prejudices? But I guess it might not, if we only ever travel to places where we’ll feel treated like kings and only ever experience Krug and caviar at the Four Seasons.

  10. @ VirtuosoEric — Well, we were planning on reaching out to an on-site anyway, but to clarify…

    When you book your ticket you have to select under which exemption you’re traveling, and then as far as I know you *can* just show up if you have a hotel booked, etc. Is that not the case?

  11. @ Paul “Cuba is anti-American? I hate to break it to you, but so is much of the rest of the world.”
    – Our feckless leader’s apology tour hasn’t fixed that yet? Shocking. Still, I would disagree with your statement, as there is a big difference between annoyance/resentment and outright state sponsored hostility. Given your false equivalency, you presumably have no problem traveling to North Korea or Iran. I just hope Obama doesn’t pay billions for your ransom like he has done before.

    @ Lucky – yeah, having principles is boring, isn’t it? The reality is that traveling to oppressive regimes directly supports them financially. If tourism/investment dollars are cut off, these regimes will fall much more quickly. This is good for their people, while financially supporting these regimes keeps their people in bondage. You might be a lost cause, but hopefully some of your readers might still consider such issues in their travel plans. But I do give you credit for not deleting comments that you disagree with (as long as they are not vulgar/threatening/etc.), so it’s good that you have thick skin. I do enjoy reading your blog, and you generally know your stuff, about travel at least 😉

  12. Four Points Havana looks terribly dated, all they did was take over an existing property there and that was recent. Starwood will have more luxury options in Havana in the next year or two so that’s when I would go. Or, stay at a more local establishment instead.

    @Lucky – Can’t you use your German passport to enter Cuba instead? Or does the US travel exemptions still apply since you’re also a US Citizen?

  13. “Still, I would disagree with your statement, as there is a big difference between annoyance/resentment and outright state sponsored hostility. Given your false equivalency, you presumably have no problem traveling to North Korea or Iran. I just hope Obama doesn’t pay billions for your ransom like he has done before.”

    I’m not an American, so your political leaders won’t be paying any ransom for me, thanks.

    You didn’t specify that you were only opposed to “state sponsored hostility” rather than endemic low-level anti-Americanism. I specified “much” of the world rather than “most”. You might like to write and read things more carefully before going into default attack mode. And assuming everyone is an American.

  14. I also plan to see Cuba sometime. But when I go I am cognizant that Communist Cuba is a parasite living off of pre-Castro infrastructure. Cuba is not a zoo-and Cubans are not zoo animals you get to see before they are ruined. The Cubans I’ve met that have come over in the last 5-6 years have told me how they kept up their parents and grandparents Chevy’s not because they were so cool, but because they could never afford a Honda Accord or a Fiat (even though Cuba has no embargo with them). They want plumbing that works in their homes and they want air conditioning–the old pre Castro units are long ago broken. Who wants to drive a 1950’s car in an ecuatorial country without air conditioning?? Reading up on Cuba for my own upcoming trip I ran across this, which shows how communism has ruined this country. And why is the Cuban food there so bad? Cuban food in Miami and LA is delicious…strange.


  15. I backpacked in Cuba for a month back kn 2006. I learnt Spanish in Mexico and Argentina, and i didnt struggle with understanding the Spanish in Cuba.
    Cuba is a fascinating country to travel in, even though the infrastructure is not in place (dont even consider taking the train). I would avoid places like Varadero and all inclusives in general and opt for airbnb/homestays. We were taken good care of everywhere.
    Shop selection is poor by any standard (90% empty) so bring all items you need such as toiletries, electronics, beach towels – even snacks. I tried finding chocolates for 3 weeks without any luck.
    I also had a chipotle mayonnaise with me from Mexico (where we came from) to take home with me after – ended up eating the whole thing while in Cuba due to bland and boring food and minimal selection and variety. Nevertheless – Cuba is worth a trip – but a week or two should be sufficient.
    The only heads up if youre travelling only females – the country has a lot of public masturbators. No joke. We experienced it in 3 different cities (at the beach), and one of the ladies in the homestay confirmed this as well.

  16. I like how an attempt at increasing the use of alternative energy source equals demonization of fossil fuels, and how an attempt at less war and a recognition of the global community of which we are, and must be, a part equal feckless. That’s some sound, objective reasoning.

  17. I jumped on the $59 WN fares out of TPA. $149 all in since they build in departure taxes and health insurance into the ticket cost.

  18. Travel has to be under one of the categories listed (https://www.treasury.gov/resource-center/sanctions/Programs/Documents/cuba_faqs_new.pdf). Journalism is one, so Lucky could travel to Cuba under that. (Essentially, his “purpose” of going is to write a review of a hotel or airline flight to Cuba… but while there he might enjoy the beach… its like having a “purpose” of going to Las Vegas for a business conference and while there you play some blackjack and go to a club.)

  19. For some reason I thought you’d fly Air China from Montreal to Havana. 😉 Just remember to buy the Cuban Tourist card at FLL from the JetBlue desk for $50. I believe you can travel there through via the general license as a journalist since you’re a blogger.
    My friends and I went last November for the Havana marathon as it fulfilled the general license for participating in an amateur athletic competition with Cubans. Back then, we flew the charter flight TPA-HAV for $450 roundtrip! That was barely an hour flight and was expensive yet the flight was still full!
    Enjoy Havana! I really think the city will change though I hope it won’t become like other Caribbean cities.
    Also, if the hotel route doesn’t work, try airbnb or casa particular.
    BTW, when was the last non-domestic flight you flew economy?!?!?! 😉

  20. Sadly, I’m too young to have had the cultural experience of visiting Nazi Germany in it’s heyday. I understand the festivities in Nuremburg were incredible.

    But visiting Cuba seems so 1960-ish. I understand they don’t even execute political prisoners by firing squad on the streets anymore.

    So I’m waiting for reasonably priced flights to North Korea. I’ve emailed Dennis Rodman about going in his private jet next time, but haven’t gotten a response yet. 😉

    Hard to believe the comment equating life in a Communist Police State with the experience of being a Black in a US inner city. Organizing an anti-police protest similar to “Black Lives Matter” (sic) in Cuba would get you a year’s free room and board in a hell-hole gulag. Whereas here it might get you invited to visit the White House. Or at least a ‘shout out’ at a press conference.

  21. @Ben as a Cuban-American who isn’t a huge fan of the Cuban accent, that comment was offensive. Dirty? Excuse me?! We have a different accent than Spaniards; that doesn’t make it dirty. And food? Like anywhere there are bad restaurants, especially those that are government-run, but with the huge growth in paladares, there are a lot of options for great food. Going to Cuba is a cultural experience, especially now that it is at a transition period. People who are opposed to supporting the government, well, yeah, some of the money you spend will go toward supporting a totalitarian regime, but if you stay at an AirBnB or casa particular, eat at paladares, take taxis, buy local art, all that money goes toward individual Cubans and decreases their dependence on the government. That said, you still can’t straight up go as a tourist. You need to be able to prove that you qualify to travel under one of the license categories. That shouldn’t be hard if you can argue you’re going for journalistic purposes, but still. And it was said before, but the embargo is very much still in place and requires an act of congress to overturn.

  22. If you are just visiting Cuba for a few days one can get what I call the Disney Cuba experience which can be perfectly lovely and charming.

    I live in Cuba and thus my perspective is a bit more nuanced, but we have many friends and family members that have very much enjoyed their visits. It is obviously undeniable though that there are some very nasty things that go on here in this dictatorship.

    As far as the Sheraton 4 Points, it’s terrible and truly a Cuban hotel experience. I would not recommend staying here at this point in time.

    If you are visiting for a short stretch, there are plenty of decent private restaurants in lovely settings where you can get good food. The restaurants run by the state are universally horrible. Bring hot-sauce wherever you go since they don’t do spice in Cuba. If you live in Cuba, the food quickly becomes dreadful since you aren’t eating every meal at private restaurants. Ingredients are very hard to come by and the food is bland and monotonous. Recently, the government has put the screws to the private restaurant owners in an attempt to limit their scope and funnel more visitors to the horrible state-run restaurants. It’s monumentally stupid long-term but is typical of the government mismanagement that is rampant here.

    There is a well-known joke in Cuba that is most appropriate, “what are the 3 worst aspects of the Cuban Revolution? Breakfast, lunch and dinner.”

  23. @Anna, “You need to be able to prove that you qualify to travel under one of the license categories.”
    No you don’t. You just need to say that you qualify. Currently, no one ever asks you to prove that you qualify or not.

  24. Slappig which travel category you travelling under? Do you plan on trying any cuban fudge brownies. ?

  25. I’m just really glad I got to see the fantastic island of Cuba and meet it’s very warm people – who by the way I found spoke great English if involved in tourism – before the place gets overrun with US tourists.

  26. Having visited last month I would completely disagree with everything peiple have told you – the people are so friendly and lovely and do speak English, especially in Havana. Money is a bit harder to get at first but by no means difficult, in fact some Australian credit cards work in ATMs. And the food is far from terrible – in fact it’s tasty and there are non Cuban food options even in the smaller towns! Especially if you only intend to travel to Havana, you shouldn’t be worried at all – Americans can get their burgers and fries no problems.
    Obviously things take planning and researching, you can’t just arrive with no reading or organising because as you said it is a little more disorganized and backwards in infrastructure etc. But thousands each year travel to remote Asian and South American cities that aren’t dissimilar.

    And things are changing rapidly so everyday you will find things improving.
    As a fellow Australian I’m pretty disappointed at your lack of adventure for visiting such an amazing country just because it might not be as shiny or easy as swiping your credit card!

  27. “…when its full of package holiday makers from the US and people treat it like Cancun and there’s no culture at all….But friends who went recently said its not an easy place to visit at all. The infrastructure isn’t there and they said every day it was just a struggle…”

    I’m with @Paul – @Ben gets Internet clown of the day award.

  28. @eponymous coward “So, no travel to non-democratic regimes that have questionable human rights records? That means no travel to China or Hong Kong.”

    Not sure why you included Hong Kong in that. The people of Hong Kong are extremely unhappy with their Communist Overlords. The only way the Communist lackeys can get elected is by the Mainland Dictators limiting who can run, and how they get elected. Just one free election, and Hong Kong would be a Free State unrelated to the Communist dictatorship.

  29. I am based in La Habana, Cuba and with introduction of cheaper fares it is possible for me to visit friends in Miami for a short weeknd visit. For those of you who think La Habana is a food desert, secetly it is becominng a foodie place …i can recommend you at least ten restaurants within walking distance of my place in Vedado, La habana. It is only those who are totally ignorant of the situation in Cuba who would rave and rant about the government. An average cuban is better off since 17 dec 2014 when Obama opened the door. Please come and see for yourself before you post anything about the moveable feast of a city La Habana

  30. “It’s a police state – but then, poor black people in many US inner cities might recognise that experience. ”

    No. Nope. Way out of line. Spoken like someone who has never actually experienced a true police state.

    Take it back.

  31. @Yehuda Kovesh, with all due respect and not to further politicize this thread but clearly most Cubans are not better off since Obama opened the door. Perhaps in Vedado, yes, but it’s a big country. A good test is the gigantic number of Cubans desperately trying to leave Cuba for other countries. That said Obama’s policy is on the mark. It will take time, however, for lives to actually improve especially since the Cuban dictatorship is doing everything possible to maintain complete control of the people.

  32. Obama did not do anything positive by visiting the island. On the contrary, most tourist see themselves without being able to buy the basic necessities like a bottle of water.

    Recently, a former co-worker tried to book a hotel in Varadero and was told that they were unable to make reservations for Americans. Another co-worker went for a week and decided to pay an extra $250 cash (no credit cards allowed) to leave 4 days before her departure date (as the situation was unbearable).

    Cuba is struggling and natives are just looking for a way out. Don’t spend your money going to an island for n which basic necessities and care is an obstacle. Wait a few years before going.

  33. The REST of the world has been enjoying Cuba for decades, with daily 747s arriving from London, and other widebodies from all over Europe. Americans complaining about Cuba and lack of this or that should just be ignored!…oh, and stay home.

  34. @ Jordan thumbs up to your comment. Americans really believe the world owes them a favor, and do think everything must be seen through their lens. I lived in Cuba for many years and as you said many direct flights from Europe have been bringing lots of tourists who have enjoyed their stay in Cuba. While life is not rosy for the cubans I believe things are changing. For those claiming they don’t want to spend their money on oppressive governments yet by clothes/gadgets from companies known for child labour and modern day slavery well get off your high horses
    @Expat in havana- “A good test is the gigantic number of Cubans desperately trying to leave Cuba…” – correlation does not necessarily equate causation. An alternative explanation for the apparent increase in people trying to cross over could be the fear that “the wet foot dry foot” policy may soon be stopped

  35. I live on the island- but in an American Naval Station. We’re in a rain shadow to boot- dry as all get out! I am surprised that no one mentioned the beautiful waters of the Caribbean as a plus. I hope that one day, the North Gate will be open, and I can visit some of the places that the expat Cubans that live here tell me about.

  36. To those that commented on the Americans failed to realize that Europeans are seen differently. Yes Europeans have enjoyed Cuba for decades without any issues. Now American are seen thru a different scope than other nationalities.

    I personally have been in Cuba more than 2 dozen times since I was a child all the way through adulthood. I have stayed in the hotels that Americans are allowed in which is not all of them and I have stayed in hostels. See I have seen the real Cuba hitching a ride on a truck to a rental car. From one providence to the other. It not the same to stay in a Meliá and think the world of Cuba versus staying in a hostel or a native’s home in a town where tourism is non existent.

    Europeans can continue going and enjoying the island and receiving the best treatment but reality is that it’s not the same for Americans or Cubans that return to the island.

    The best education anyone can receive is to travel because you see the truth through your eyes. Hence, don’t stay in nice resort and travel the island just a wearing a backpack and carry Cuban currency, watch how your view will chance. Meliá will not want you without your Euros. TRY to LEAVE YOUR EUROS AT HOME. Hopefully you are not a socialist or a communist and are able to see the truth.

  37. Yes I have been to Cuba as a North American. First time flying from El Salvador to attend an international natural disaster mitigation conference with a Salvadoran EMS agency in 1999. Then a second time crossing from Wa. State to Vancouver BC and flying directly to Varadero airport and hitchhiking to La Habana in 2000 and a third time again through Vancouver end of 2001. And now a fourth trip via Vancouver and I am currently in Distrito Federal Mexico City ready to get on the plane. I’m sure there are lots of changes over the last 15 years since I have been.

    Suddenly a presidential visit and The Rolling Stones are sparking an interest for Americans to travel there?

    We always have.
    Maybe not main stream travel.
    But that’s what made it special.

  38. Does anyone know how things REALLY work NOW when travelling to Cuba? I have read on a Jet Blue site that one must book a ticket to Cuba at least 14 days prior to travel. Jet Blue representative could not actually provide a coherent answer if at all or why is it necessary to do sol. Also I was wondering about the 12 different “reasons” one must check. Does anyone anywhere really double check this or is it just a pure formality? I am a little weary of buying a ticket and then not being able to even board the plane.

Leave a Reply

If you'd like to participate in the discussion, please adhere to our commenting guidelines. Your email address will not be published. Required fields are marked *