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Is Cuba Worth Visiting? The Surprising Reality of Travel · Phil and H Travel - Is It Worth It? Top Travel Destinations Explored!

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  Welcome back to the Deep Dive. Today we are taking you
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  somewhere that you know it exists right now in 2024, but it
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  feels, well, it feels totally removed from.
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  It it really does. We're diving into Cuba, the
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  legendary land of, you know, rum, rumba and revolution.
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  It's a place most of us have seen in these incredible photos.
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  Classic cars, Sun drenched colonial buildings.
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  And that's the image, right? The island preserved in amber.
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  But as our source material for today, a whole stack of recent
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  travel accounts and logistical guides makes really clear, Cuba
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  is a place of immense complexity.
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  It's challenging. It's vibrant and beautiful, yes,
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  but the actual act of travelling there now is demanding.
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  It's rewarding for sure, but also really thought provoking
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  and that. Complexity is exactly what we
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  need to unpack today. Our goal is to give you the
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  shortcut to being truly informed about a trip to Cuba to go way
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  beyond the glossy travel brochures.
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  Right. We've looked at all these real
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  world accounts, the logistical workarounds you absolutely have
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  to know, the cultural immersion, and I think most importantly the
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  ethical and financial side of visiting Cuba right now.
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  So our mission today is to answer 1 central question.
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  Is it worth it? Exactly.
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  Yeah. Is this completely unique
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  experience, with all its hurdles, its economic
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  strangeness, and the the forced digital disconnect, is it truly
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  worth the effort for a modern traveler?
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  To figure that out, we're going to go step by step.
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  We'll start with the non negotiables, the money, the
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  visas, and then move to where you should ethically sleep, what
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  you'll actually eat, and the cultural experiences that will,
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  you know, really define your memory of the island.
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  It sounds like planning is absolutely mandatory.
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  So to do that right, we have to start at the very beginning.
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  OK, let's unpack this, starting with what you call the
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  logistical gauntlet. Absolutely, because before you
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  get to the mojitos and the music, you have to get through
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  this trio of friction points, cash categories and
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  connectivity. These are the hurdles that
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  define Cuban travel, especially for Americans.
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  And if you get them wrong. Your trip is derailed almost
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  immediately. OK, so let's start with the most
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  confusing one, the visa and the whole US embargo situation.
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  For a lot of nationalities, getting a tourist card for Cuba
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  is pretty simple, right? You just get it through the
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  airline. It's straightforward for most of
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  the world, but the second you're holding an American passport or
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  even just flying from the US, the rules change completely.
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  Because of the embargo. Exactly. the US Treasury
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  Department technically bans travel for tourism, so you can't
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  just go for a beach holiday in the typical sense.
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  Your trip has to fall under 1 of 12 very specific approved
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  category and. That's a crucial distinction, I
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  imagine. It dictates everything.
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  It mandates a whole style of travel if you want to be
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  compliant with U.S. law. So which of these 12 categories
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  is the one that most independent travelers actually use?
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  Well, the one almost all our sources focused on is called
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  support for the Cuban people, which.
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  Sounds kind of vague. It sounds vague, but in practice
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  it's very specific. It's much more than just a box
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  you tick on a form. It fundamentally dictates how
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  and where you spend every single dollar.
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  It means you need to have a genuine, demonstrable commitment
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  to supporting local private entrepreneurs.
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  You have to be able to prove, if you were ever audited, that your
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  itinerary was built around supporting the Cuban private
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  sector, not the state. So in practice, that means yeah,
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  choosing certain hotels and restaurants.
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  It means choosing private homes, the casas particular is over the
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  big government run hotels. It means eating at private
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  restaurants, the paladares, instead of the official tourist
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  spots. You're consciously directing
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  your money away from the state and toward the people.
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  That's a really interesting point about risk.
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  This is all self reported right here.
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  You're just declaring that you fit the category.
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  It is. The risk isn't really on the
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  island itself. The risk is the however small
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  possibility of an audit by the US government when you get back,
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  and then you'd have to prove you were compliant.
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  So you need to keep records. Precisely.
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  The advice is to keep receipts from your casas and pallidaries.
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  Keep a detailed itinerary, a log of your daily activities.
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  It's a level of documentation that's, you know, totally
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  foreign to how most of us travel today.
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  It basically turns your trip into a form of direct economic
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  support. OK, so if that visa friction
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  wasn't enough, this idea of supporting the people leads us
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  right into the next huge hurdle. Yeah.
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  Money. Yes.
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  The golden rule of Cuban travel. And we have to state this really
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  clearly, right? Cuba is a cash society.
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  A total cash society and when we say that we mean there is 0
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  functional digital banking for foreigners, especially anyone
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  connected to the US banking system.
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  Your credit cards, your debit cards, they they just will not
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  work. Not at all.
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  No exceptions. Virtually none.
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  They won't work in the few ATMs you might see.
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  They won't work in the hotels. They certainly won't work in a
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  shop or a private restaurant. Period.
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  And that has huge implication. It's profound.
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  It means you must bring every single cent you plan to spend
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  for the entire trip in physical cash.
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  You have to budget meticulously before you even get on the
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  plane. So let's talk about that budget.
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  What do the sources recommend? How much cash are we talking
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  about for say, a week? For a comfortable mid range
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  trip, not including your flights, you should plan on
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  about 100 to 150 U.S. dollars per person per day.
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  OK, so that would cover your room.
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  Right, a nice Casa particular for 30 to $50 a night, A couple
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  of good meals at paladares, some drinks, maybe a taxi or a museum
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  entrance. So for a 7 day trip, you're
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  carrying somewhere between 700 and 1050 dollars per person in
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  cash. That is a lot of physical cash
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  to be carrying around. So what currency should you
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  bring? I'd automatically think U.S.
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  dollars, but that's not the recommendation, is it?
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  No, the sources are really clear on this.
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  Because of all the sanctions, the US dollar can sometimes get
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  hit with an extra fee, maybe 10% or just a really bad exchange.
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  Rate. So it's better to bring EUR or
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  Canadian dollars? Exactly.
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  You'll often get a cleaner, better exchange rate.
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  You bring those currencies and then you exchange them for the
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  local currency, which is the Cuban peso, the CUP.
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  And this is where things get really interesting.
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  You call the exchange dilemma the official government rate
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  versus the the informal St. rate.
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  This is the absolute core of the economic friction on the ground.
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  You can go to an official government exchange house, a
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  Kadeka. It's safe, it's legal, but the
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  rate is terrible for you as a traveler.
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  But there's another option. There is, you very quickly learn
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  about the informal market rate, it's offered by private
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  individuals and it is significantly better.
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  How much better are we talking to?
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  Do the sources give actual numbers?
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  They do, and this is critical. The informal or street rate can
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  offer you 2 1/2 to three times more Cuban pesos for your euro
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  or dollar than the official rate.
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  Wait three times. Up to three times.
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  Think about that. Your spending power.
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  Literally triples if you can navigate this exchange safely.
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  Wow, that's a staggering difference.
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  It basically determines whether your trip is affordable or
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  incredibly expensive. It's everything, and this is
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  where the whole idea of support for the Cuban people comes back
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  in a very practical way. Through your Casa host.
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  Yes, your Casa particular host is your trusted lifeline here.
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  The sources all say they play this vital role in helping you
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  exchange money safely at the good informal rate.
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  They connect you to the real local economy.
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  So your host is the gatekeeper not just to a place to sleep,
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  but to your entire trip being financially viable.
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  Exactly. If you try to do it on the
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  street by yourself, you can get scammed.
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  But going through your host, you build this immediate
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  relationship of trust. You're maximizing your ability
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  to spend money with the very people you're there to support.
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  That makes so much sense. OK, so you've got your Visa
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  category sorted, you've got a wallet full of euros.
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  What's the third logistical hurdle?
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  Connectivity, or more accurately, the profound lack of
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  it. You cannot just turn on your
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  phone's data roaming. It won't work.
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  So how do you get online? The whole system is centralized
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  through the state telecom company ITEXA.
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  You have to physically buy Wi-Fi cards.
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  They're literally little scratch off cards with a username and
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  password. A scratch off card like for a
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  lottery ticket. Pretty much.
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  And they're good for a certain number of minutes or hours.
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  Typically, an hour of Internet costs about one or two US
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  dollars. And where do you buy it?
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  Well, you can buy them at official Atex offices, but the
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  lines can be really long. You can wait for half an hour.
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  And you can't just buy a huge stack of them either.
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  So once you have your precious scratch off card, you can't just
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  use it in your room. No, you have to find a public
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  Wi-Fi park, the sources say. They're instantly recognizable.
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  You just look for the cluster of people, young and old, all
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  huddled together staring at their phones.
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  That's the hotspot. You log in, use your minutes,
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  and then you're done. The connection is slow.
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  It's public, it is not for remote working.
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  Which leads to the most critical piece of pre trip prep.
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  You must download everything, everything you could possibly
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  need before you leave home. Offline maps.
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  Offline maps are a lifesaver. The app maps dot me is mentioned
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  again and again. You need your accommodation
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  details, your host's phone number, an offline translation
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  app. You can't just look it up when
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  you're there. So the deep insight here is that
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  this lack of Internet forces you to be present, right?
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  It slows everything down. It does.
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  It forces a kind of digital detox, which can be amazing.
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  But that benefit only works if you've done the practical
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  planning. If you haven't downloaded your
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  MAP, it's not a detox, it's a disaster.
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  It's a high barrier to entry, but also a cultural reset.
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  Absolutely. So we've navigated the gauntlet.
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  You've got your cash. You've got your downloaded map.
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  The next big decision you make seems to shave the entire rest
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  of the trip where you stay. This is what we're calling the
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  ethical and experiential core of the trip, and we would argue
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  this choice is the single most important decision you'll make.
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  It's not just about a bed. And the sources are completely
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  united on this, aren't they? The definitive choice is the
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  Casa particular. 100% it translates to private house and
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  it's basically the Cuban version of AB and B or A homestay.
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  They're easy to spot. You look for a little blue
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  anchor sign outside the door. And this ties directly back to
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  that support for the Cuban people mandate.
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  It's the most direct and powerful way to fulfill it.
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  Your money goes straight into the pocket of a Cuban family.
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  It bypasses the big state owned hotel corporations and actually
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  benefits the local economy. But crucially, it's not just an
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  ethical choice, the sources say. The experience is just better.
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  It's vastly superior. Your Casa host is so much more
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  than a landlord. They're your concierge, your
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  fixer, your lifeline. They fill all the gaps left by
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  the, you know, the challenging state infrastructure A.
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  Lifeline. I like that framing.
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  What kind of specific things are they helping with?
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  Everything we just talked about, they'll help you with that safe
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  currency exchange. They'll give you honest
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  recommendations for the best private restaurants, the
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  paladares that you'd never find on your own.
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  And travel between cities. This is critical.
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  They arranged the shared taxes, the clotivos, which are
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  essential for getting between places like Havana and Vinales.
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  The official buses can be slow and unreliable.
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  Your host finds you a fair price and a safe driver.
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  The sources really highlight this personal connection.
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  They mentioned a host in Vinales named Elena who would just sit
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  with her guests and share stories about her family and
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  daily life. You don't get that at a hotel
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  front desk. No, you don't.
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  That's the genuine cultural exchange that transforms a trip,
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  and it often starts first thing in the morning with breakfast.
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  The breakfast get rave reviews. Consistently the best meal of
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  the day, they describe these amazing spreads of fresh
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  tropical fruit, guava, mango, papaya that tastes better than
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  anything you can buy in a supermarket back home, plus
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  fresh bread, eggs and that incredibly strong, sweet Cuban
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  coffee. And this all stands in stark
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  contrast to the state-run hotels.
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  The critique of the state hotels is pretty blunt.
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  They're often dated. Maybe the hot water is
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  inconsistent. The service can be indifferent.
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  The food is almost universally described as mediocre.
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  And they isolate you. They're designed to they create
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  a tourist bubble. A Casa is often cleaner, cheaper
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  and it immerses you in the real Cuba.
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  It is the absolute linchpin of a successful trip.
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  And that linchpin then sets you up for the next challenge, the
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  food. This is what you call the
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  culinary contradiction. Yes, because Cuban food, well,
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  it has a reputation, doesn't. It for being a little bland,
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  maybe repetitive. And that reputation isn't
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  totally unfair. You have to set realistic
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  expectations. This is a direct result of
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  decades of economic hardship and food shortages.
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  The state rationing system puts huge constraints on what chefs
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  can get. And you see that reflected in
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  the state-run restaurants. You do, they often serve just
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  basic sustenance, you know, dry chicken or pork with some plain
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  rice, beans and maybe some sad looking boiled cabbage.
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  It's fuel. It's not a culinary experience.
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  But just like with the Casas, the private sector is driving a
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  renaissance here with the palladers, the private
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  restaurants. This is where the magic happens.
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  This is it. These private chefs are
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  incredibly sourceful. They're driven by competition.
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  They have to create high quality, innovative meals to
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  attract travelers. They're often sourcing
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  ingredients from, let's say grey markets to get the best produce
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  or fish. The existence of a good paladar
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  is a story of resilience in itself.
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  It really is. It's a culinary scavenger hunt
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  and again, you need your Casa host to give you the real up to
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  date recommendations. So what are the must try dishes?
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  If you find a good paladar, what should you order?
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  The national dish is ropa vieja. It translates to old clothes
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  which. Doesn't sound very appetizing.
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  It doesn't, but it's this incredibly rich, comforting dish
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  of shredded beef slow cooked in a tomato based sauce with
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  Peppers and onions. When it's done right, it's so
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  tender and flavorful. It's the ultimate Cuban comfort
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  food. And what about seafood?
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  Absolutely. Especially in coastal towns like
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  Trinidad, you can get amazing fresh caught fish or lobster,
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  often just grilled simply with garlic and lime.
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  It's simple, clean and delicious.
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  And for quick lunch. The Cubano, The Cuban sandwich.
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  The sources point out that the authentic version is actually
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  simpler than the big, overloaded Miami style.
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  It's usually just roast pork, ham, Swiss cheese and mustard on
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  pressed Cuban bread, but it's fantastic.
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  You also have to talk about the fruit and the drinks.
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  The fruit is on another level. The pineapples, the mangoes,
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  just incredible. Which means the fresh fruit
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  juices, the potitos, are a daily necessity.
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  A way to stay hydrated in the heat and they're.
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  Delicious. And then there's the coffee.
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  It's strong, it's dark, and it's usually served very, very sweet.
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  It has enough power to, as one source, put it jumpstart a car.
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  So the final verdict on the food is that it's worth it if you do
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  your homework. Exactly.
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  You have to be deliberate. Stick to the paladar as your
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  host recommends, manage your expectations, and embrace the
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  simple, rustic, delicious flavors.
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  OK, so once you've got your logistics, your lodging and your
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  food strategy locked in, you can finally just experience the
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  place. This brings us to the must do
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  activities. And we've organized this across
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  the three key locations from the sources, Havana, the city,
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  Vinales, the countryside, and Trinidad, the coast.
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  Let's start in Havana, the chaotic, beautiful heart of it.
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  All It's one of the most intoxicating cities on earth.
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  It's this incredible mix of color, crumbling beauty, and
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  just constant rhythmic motion. And the first thing to do is
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  just get lost. Yes, just wander through Old
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  Havana, Habana viea, the sources say.
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  The real joy is the sensory immersion.
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  Getting lost in the cobblestone streets, seeing the laundry
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  hanging from balconies, hearing the music spilling out of
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  doorways. It's like walking onto a movie
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  set. A living, breathing 1.
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  You can feel the history in the peeling paint.
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  It's centuries of elegance with decades of neglect layered on
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  top. And that wandering will lead you
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  to the big public squares like Plaza Vieja.
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  And the advice there is not to just snap a photo and leave.
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  It's to sit down, find a bench in the shade, grab a drink and
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  just absorb the atmosphere. Listen to the street musicians.
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  They're the soundtrack of the city.
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  And then there's the one thing that's super touristy.
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  But everyone says you have to do it.
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  The classic car cruise. It's a cliche, but it's worth
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  it. 100% worth it. You negotiate an hour long tour
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  in a bright pink 57 Chevy convertible.
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  It's essential. And what's the best route?
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  You want to loop that goes past the Capitolio, through
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  Revolution Square, and then this is the key part, cruising along
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  the seawall, the Malecon, ideally around sunset.
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  It gives you this incredible sense of the city's scale and
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  its soul. Just remember to negotiate the
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  price first. Always aim for around 40 to
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  $60.00 for the hour. But Havana isn't just a museum.
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  There's a really vibrant contemporary culture scene there
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  too, right? Yes, and the epicenter of that
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  is the fabric of the Arctic Cubano, or FAC.
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  It is an unmissable stop. It's a converted factory.
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  A huge old cooking oil factory that's been transformed into
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  this multi level art gallery, nightclub, performance space and
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  cinema. It's this amazing sprawling
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  complex. And it showcases modern Cuban
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  art. Exactly.
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  Photography, sculpture, live jazz, modern dance.
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  It's a necessary counterpoint to all the history.
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  It shows you that Cuban culture is alive and innovating right
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  now. The atmosphere is incredibly
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  cool. OK, so from the energy of
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  Havana, we move to the countryside to Vinales.
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  A complete change of pace. It's a few hours drive and
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  suddenly you're in this UNESCO World Heritage site that is just
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  breathtakingly beautiful. This is where you see the
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  Magotas. Yes, these incredible sheer
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  limestone mountains that just just straight up from the flat
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  valley floor, it looks almost prehistoric and the earth is
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  this rich deep red color. And that's where they grow the
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  tobacco. The best tobacco in the world
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  and the absolute must do activity.
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  Here is a tobacco farm tour which fits perfectly with the
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  support for the Cuban people idea.
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  And you often do this on horseback.
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  Which is an experience in itself.
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  Riding through the valley, a local farmer guides you through
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  the whole process. The growing, the drying in the
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  rustic curing barns, the fermentation.
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  It's fascinating. And they explain the economics
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  of it, right? They do.
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  They have to sell 90% of their crop to the state at a fixed low
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  price, but they get to keep the other 10 to sell directly to
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  visitors like you. And that 10% is where the real
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  cultural reward is. It is at the end of the tour.
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  You sit down with the farmer and he'll hand roll a fresh cigar
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  for you right there. And they have a special local
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  tip. Dip the end in a little bit of
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  local honey before you smoke it. It cuts the harshness and
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  honestly it's a better, fresher and way cheaper cigar than the
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  official state-run Cohibas you'd buy in a shop.
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  It's a perfect authentic experience.
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  OK, so from the green valleys to the coast, the colonial jewel of
• 19:00
  Trinidad. Trinidad is like old Havana's
• 19:03
  smaller, more relaxed and almost perfectly preserved cousin.
• 19:08
  Another UNESCO site. The cobblestone streets, the
• 19:11
  candy colored houses, the sources just call it painfully
• 19:15
  beautiful. It's stunning during the day,
• 19:17
  but the sources say the real magic happens after dark.
• 19:20
  It transforms and it's all centered around the Casa de la
• 19:22
  Musica, but it's not a club. It's the steps.
• 19:25
  It's the big wide stone steps next to the main building.
• 19:28
  They become this natural amphitheater.
• 19:30
  Every night, local bands play live salsa and Sun Cubano right
• 19:34
  there under the stars. And everyone just gathers.
• 19:36
  There, the whole town comes alive.
• 19:37
  You grab a mojito or a cold crystal beer and you just sit on
• 19:40
  the steps and listen. The energy is infectious.
• 19:44
  And people dance. Locals, tourists, old, young,
• 19:48
  everyone gets up and dances. It's this incredible, joyful
• 19:52
  communal experience that just perfectly captures the spirit of
• 19:55
  the country. So Havana, Vinales, Trinidad.
• 19:59
  That sounds like a perfect cross section of Cuba, but just as
• 20:02
  important as what to do is what not to do.
• 20:04
  The skip list. This is Section 5.
• 20:06
  It's about saving you time, money, and frustration.
• 20:09
  First up, as we've said, skip most state-run restaurants, and
• 20:12
  I'd add most state-run museums to that list as well.
• 20:15
  Why the museums? Many of them are described as
• 20:17
  just dusty propaganda halls. The experience of the living
• 20:21
  culture on the streets, the music, the people, the
• 20:23
  architecture is just so much more powerful than the often
• 20:27
  biased exhibits behind glass. I would also say emphatically
• 20:30
  skip the all inclusive resorts, places like Varadero.
• 20:33
  Absolutely. They're just two tourist
• 20:35
  bubbles. They're totally isolated from
• 20:37
  the real Cuba that you're there to see and support.
• 20:39
  If you want a great beach, go to a local 1 like Playa Ancon near
• 20:42
  Trinidad instead. The sources also warned about
• 20:45
  being aware of some minor scams. The most common one is the milk
• 20:48
  for my baby. Scam right?
• 20:50
  Someone, often a woman, will ask you to buy expensive formula
• 20:54
  from a specific shop saying she can't afford it.
• 20:56
  The reality is she gets a kickback from the shop owner.
• 20:59
  So how do you handle that? Just be aware, not paranoid, a
• 21:03
  polite but firm no gracias is all you need.
• 21:07
  If you want to help, buy some food yourself at a market and
• 21:09
  give it directly to someone. And the final thing to skip over
• 21:14
  scheduling. This is so important.
• 21:16
  Travel in Cuba is slow. The roads are not great, the
• 21:19
  cars are old. A three hour journey on a map
• 21:22
  can easily take five hours. So the recommendation is to
• 21:25
  focus on just two or three cities and embrace that
• 21:28
  slowness. Exactly.
• 21:29
  Building buffer time. Don't try to cram too much in,
• 21:32
  Allow for the unexpected. That's where the best moments
• 21:34
  happen. So after navigating all of that,
• 21:37
  what's the lasting impression? What's the real vibe of the
• 21:39
  trip? The one word that comes up over
• 21:41
  and over again is resilience and contradiction.
• 21:44
  You see the crumbling buildings and the empty shelves, but it's
• 21:47
  set against this incredible, vibrant human spirit.
• 21:50
  That resilience comes through in the joy.
• 21:52
  It does. There's music everywhere.
• 21:54
  People are incredibly educated and want to talk.
• 21:57
  There's this warmth and generosity that exists despite
• 22:00
  all the hardship. The country basically runs on
• 22:02
  human connection, not on Wi-Fi. And that digital disconnect
• 22:05
  becomes a huge part of the experience itself.
• 22:08
  It's transformative. You are forced to put your phone
• 22:10
  away. You have to make eye contact,
• 22:12
  listen to the music, slow down. The lack of digital convenience
• 22:16
  forces you into genuine human interaction.
• 22:19
  It's a place of contradictions, then, beautiful and decaying,
• 22:22
  joyful and frustrating. Simple and deeply complex all at
• 22:26
  the same time. Which brings us back to our
• 22:28
  ultimate question After all of this, the logistical friction,
• 22:32
  the ethical choices, the intense planning, is a trip to Cuba
• 22:36
  really worth it? You know, for the traveler
• 22:38
  looking for an easy, predictable, seamless beach
• 22:40
  vacation, the answer is no, absolutely not.
• 22:43
  Go to Cancun. Cuba will only frustrate you.
• 22:46
  But. But for the adventurous, open
• 22:48
  minded traveler, the person who is looking for a challenge, for
• 22:51
  cultural depth, for real human engagement, the verdict from all
• 22:55
  the sources is a resounding yes, 100% worth it.
• 22:59
  It's not a vacation, it's a journey.
• 23:01
  It's a profound journey. It's powerful because it forces
• 23:03
  you to engage, to slow down, and to see a country and its people
• 23:08
  with incredible grace and resilience.
• 23:10
  It will stick with you long after you get home.
• 23:13
  And that's our deep dive into the beautiful, complex, and
• 23:16
  challenging reality of travel in Cuba today.
• 23:20
  We covered the logistics of cash and categories, the ethics of
• 23:23
  staying in Casas, the hunt for great Paladaris, and the
• 23:26
  unmissable culture of Havana, Vinales and Trinidad.
• 23:30
  And I think the biggest take away really is that idea of
• 23:33
  resilience and the forced digital detox.
• 23:36
  The most valuable part of the trip is seeing a society that
• 23:38
  thrives on human connection in the almost total absence of the
• 23:42
  digital convenience we all take for granted.
• 23:44
  Which leads to one final provocative thought for you to
• 23:47
  take away. Since a trip to Cuba forces you
• 23:49
  to live without constant Wi-Fi, the sources make you wonder what
• 23:52
  other areas of your own life, your work, your relationships,
• 23:55
  your community are maybe running on the thin convenience of
• 23:58
  technology rather than the effort and depth of real human
• 24:01
  connection. It's a challenging question and
• 24:04
  Cuba offers a really fascinating, vibrant
• 24:07
  counterexample to our hyper connected lives.
• 24:10
  Thank you for tuning in to the Deep Dive.
• 24:12
  You can find links to more information, including some
• 24:15
  suggestions for Acasa's and Pella Dairies, in our show
• 24:17
  notes. Until next time, pack your bags,
• 24:19
  pack your cash, and most importantly, pack your
• 24:21
  curiosity. Safe travels.