51 Random Thoughts on Traveling to Cuba

I’m not going to lie to, ya. Not going to front. Traveling to Cuba was wild.

Certainly not for the faint of heart.

The combination of communism, well a dictatorship – meeting cheap rum, world-class cigars, and pumping nightlife are enough to send any man into culture shock.

Oh, and don’t get me started on Las Cubanas.


The place is completely, utterly unexpected and different than anywhere else I’ve ever been in Latin America.

And I’ve been all around the region.

From Colombia

To Mexico.

A stop in Peru.

And then back, again.

Cuba is a whole different animal. A beast. Something of a communist shithole mixed with elegant charm and friendly people.

Honestly, I couldn’t really put a finger on it. Traveling in Cuba was such an experience. Such a unique country to travel in.

Some aspects made me never want to leave. Others made me curse Fidel under my breath.

And then book the first flight back to civilization.

51 Random Thoughts on Traveling to Cuba

But I didn’t book nothing back.


I stuck it out for my six days in Cuba and explored the communism-riddled Caribbean nation as best I could.

Made memories I’ll never forget.

Drank way too much cheap, high-quality Cuban rum and smoked more Puros than ever before.

And while traveling in Cuba, I took notes.

See, normally, I send tweets about my day-to-day life. Observations. Stuff of the like.

While traveling to Cuba, that’s simply not an option. So, I brought a notebook and wrote down my random thoughts into that journal.

A journal that I turned into a Twitter thread.

And now, this here blog posting you’re reading.

But enough of my fluff, if Cuba travel tips and tricks are on your mind, keep on reading.

Here’s one gringo’s random thoughts on traveling in Cuba:


First and foremost…

Cuba is a mindfuck.

Like raw. No lube-level mindfuck.

Excuse my French.

But I simply cannot articulate my overall feelings on the country in any other way.

Sometimes you absolutely adore Cuba and won’t want to leave. It’s magical in many ways.

Other days, you will think about heading down to the local WiFi hotspot and booking the first flight out of Havana ASAP.

The ups and downs of life in Cuba are certainly something I’ve never experienced before.


I haven’t experienced culture shock in years.

Generally, I’m comfortable in Latin America.

I speak some Spanish, understand the culture, have some damn honest hips, and enjoy some abject degeneracy from time to time.

In Cuba, I was shocked.


Not sure what to call it.

The mixture of communist skull-fucking combined with old-world architecture is truly a sight to behold.

Everything about the country is so unique, yet so confusing.


And it all started as I rode into the city in a taxi…

There’s no traffic in Cuba.

People can’t afford cars.

For a city of 2+ million, there’s no such thing as traffic.

I can’t remember sitting in traffic once during my whole time in the country.

I doubt any other big city in the world has as little traffic as Havana does, especially in the center.


Then I got to my Airbnb.

The host was waiting for me outside the place.

The guy was friendly as hell.

But a bit off…

Jittery. Or nervous.

Honestly, I couldn’t put a finger on it. Don’t get me wrong…

He was a great guy, but almost too friendly at first.

It took me a while, but I finally figured out why. And unsurprisingly, it all came back to Fidel and his cronies royally screwing things up.


Everyone in Cuba is equally screwed.


Damn near everyone.

Expect the lady who changed my money at the hotel from her purse…

She had damn near $10K USD / CUC in cash.

No idea how, either 😉


And due to the equality of the screwing by ole’ Fidel and friends…

You can’t judge a book by its cover in Cuba. At all. Whatsoever. Nobody has it good in the country.

  • Tall / Short
  • Good looking / Ugly as sin
  • White / Black / Brown / Asian
  •  Intelligent / Not so intelligent

…Doesn’t matter in Cuba.

Life is tough and rough for every single person.

In some ways, this is probably a good thing.

But overall, probably not. In my opinion, it’s better for some people to be successful – than everyone be equally screwed.


And while people seem screwed from a western perspective, Cubans damn sure seem to make the best of it.

People laugh.

Drink cheap rum.

Smoke world-class cigars.

Play sports all day and night.

Make sweet love.

…After all, they say the best things in life are free.

Or at least close to it.


Oh, and speaking of Fidel.

Dude is alive and well throughout Cuba.

Fidel propaganda still reigns supreme throughout the country.


Around every corner.

If you can walk around for 20 minutes and not see his face somewhere, I’d be quite surprised. Baffled, to be honest.


Speaking of the economy and money in Cuba…

I believe the average salary in Cuba hovers around $25 CUC. Well, that’s what I was told.

Which equates to like $25 USD and/or $700 Cuban Pesos.

I was told a doctor makes less than $100 USD a month in Cuba.

But a military officer makes twice that.

A whopping $200 USD!

Upon further investigation, this number is still quite low – although not as low as some Cubans in Havana want you to believe (Source).

Cuban money.


Due to the difficult economic conditions, the whole non-state sponsored economy is basically run on tourist dollars in Havana.

Tourism is everywhere.

And everyone wants a piece of the action.

You can’t blame them.

Making a couple deals with a tourist each month can easily double or triple what they would normally make from their “real” salary.


While nobody seems to make much money, there’s legitimately no crime in Cuba.

Part of the confusion when traveling in Cuba…

You can walk around any backstreet and no one will rob you.

Well, at least not locals.

Many Cubans told me that the country has tons of economic problems, but it’s the safest place in the Caribbean.

I have to say that they’re correct.

It seems that investing all your money into your shitty military and severely reprimanding anyone who gets caught in a crime is probably the best part of communism.

Because it actually worked.


While the safety is ideal for tourist, every other aspect of the country is not.


That’s only half true.

Cuba is part amazing and part awful. Often at the same time.

That’s why it’s such a culture shock for many, even seasoned travelers like myself who figured Cuba would just be another stamp on the passport.

…Cuba is anything but!


Some people claim Cuba is one of their best travel experiences of all-time.

Cuba is unique and intriguing for 3-4 days, but after that, it wears on you.

But I quickly realized the type of people that fell in “love” with Cuba.

If you take asinine amounts of Instagram photos to ensure people think you’re far cooler than you actually are…

You’ll love Cuba.


However, if you’re like me the place might get to you after a few days.

Basic luxuries we take for granted are often impossible to find in Cuba.

If you want to sit in bed watching Netflix while nursing a massive hangover after too much Caribbean rum…

Well, that’s not going to happen.

Nor is much else.


Because nothing in Cuba works.

First, let’s look at the Internet.

Don’t get me wrong…

Not having Internet for a few days isn’t a huge deal, but not having Internet for damn near a week is annoying.

Plus, in Cuba…

You pay $1.50-5.00 USD for an hour of the Internet – depending on the location and speed of the Internet.

Aka the quality of the Internet and the location you’re using it at.

At nice hotels, it’s $3-5 USD to log on. At certain public parks, it’s only $1.50.

You have to buy a card:

Internet in Cuba.

The Internet is so slow that you cannot even get a speed test to run.

Yet, it does work and it is available.

It’s just a huge pain in the arse to access. Oh, and it goes in and out every 15 minutes. Don’t plan to live like a digital nomad while in Cuba. Trust me on that one.


For this reason, Cuba might be one of the only countries in the world where it is far preferable to stay in a hotel.

In a hotel, you’ll often get a few amenities and some WiFi in the lobby. This is far preferable to lugging your laptop to a park and sitting on concrete.

For budget hotels, I couldn’t recommend Hotel Deauville enough.

This was next to my Airbnb and I went every day to get WiFi. The pool is trash, but the location is ideal and the WiFi works well enough.

If you want to do Cuba right, I’d recommend Hotel Parque Central.

This place is located right next to the best tourism in Havana.

The rooftop pool could be described as baller and the WiFi in the lobby was the fastest I found in the city.

Nicest hotel I saw in Havana.


Casa particulares are basically apartments or a room in an apartment that’s rented out by someone living nearby or in the same building.

The host generally helps guest get acclimated to Cuba, offers tours, and can cook breakfast for you.

Personally, I stayed in a casa particular I found on Airbnb.

I highly recommend booking a casa particular on Airbnb – if hotels don’t suit your needs.

This way you don’t have to carry more cash in Cuba than you need to.

Plus, the hosts know that you can influence their business on Airbnb with a review. So, they put in a little extra effort on the hospitality side of things.

P.S: If you’re new to Airbnb, get $40 off your first rental here!


If you can afford a hotel over a casa particular while in Cuba, go that route.

If not, casa particulares on Airbnb are just fine.

You can also have a guest over to a casa much easier than at a hotel – if that’s up your alley.

Although, some casa owners will want you to register the guests in their “log” or whatever they call it.


You’re going to get tourist prices in Cuba one way or another.

That’s just the reality of how the country works.

But learning some Spanish before you go would be exceptionally useful.


Because Cuban Spanish is straight Caribbean slang and hard as hell to understand.

You’ll want to have some type of grasp on the language before going. Speaking a little Spanish also helps with negotiating and not getting scammed too hard.

P.S: If you’re looking to learn, this is the absolute best way I’ve found.


There are some exceptionally intelligent and educated individuals in Cuba.

But overall, English levels in Cuba aren’t great.

You’ll find a number of people who speak broken, “I sell shit to tourists” English.

But actual comprehension and conversational skills…

The levels are low here.


Now, it may seem that I’ve been a little harsh on Cuba overall.

And trust me…

That’s for good reason.


Because nothing in the country works at all like it should in 2018. Cuba is decades upon decades behind the time – and the people have faced untold economic oppression of the highest order.

But the country still has a ton to offer from a pure tourism perspective.


To begin…

Havana, Cuba is one stunning city.

With wonderful ocean views, a stretching oceanfront Malecon, and old-world architecture galore – it’s like you’re stepping back in time.

While the downsides of crumbling buildings are felt by the locals, they certainly make for stunning photos.

And then the classic cars on top of it all are simply icing on the cake…

Exploring the city is well worth a couple of days.

And I highly recommend taking the citywide bus tour for a couple hours to get a feel for the place.

Click here to learn more.


Once the rundown buildings start to wear on you, it’s time to get out of Havana and explore other parts of Cuba.

The island is far bigger than anywhere else in the Caribbean. So diversity abounds and there’s a lot of places to check out.

I stayed close to the capital, but did manage to check out:

-> Vinales
-> Playas del Este


Both places are truly stunning and well worth a visit.

Just check out this picture of Vinales…

Views in Vinales.

The small mountain town is a little over two hours from Havana and filled with stunning views and tobacco farms.

More than worth a visit, but don’t make the same mistake I did.

Don’t take the state-sponsored tour here. It’s just not cool. Too many people. Way too much propaganda.

Talk to your casa particular host about a private tour. Many of the hosts will know drivers that can take you.

You’ll want to go early in the morning and find a tobacco farm that actually gives you a real tour and lets you smoke legit cigars – often that they just made.

Plus, you’ll be supporting local Cubans and not the corrupt government.

Next up, Playas del Este is just 30 minutes outside of Havana.

The beach town offers white sand beaches, crystal blue waters, and relaxation.

Just don’t go on the weekend!

It gets way too packed.

The bus leaves from Parque Central throughout the day and only cost $5 bucks for a roundtrip.

Walking to the beach…


Overall, there’s tons of things to do in Cuba.

And many of them are great fun.

My only issue is…

All the tourism agencies are state-sponsored.

So, you’re force-fed communist propaganda in both Spanish and English on these tours.

It’s a bit annoying hearing about how great communism is when the whole country is damn near falling apart.

And even if you don’t take a sponsored tour, the buses are still run by the government.

You can’t escape the long arm of Fidel…

No matter how hard you try.

If you have the budget, always hire a private driver from your casa. They get the money and you’ll have a far better experience.


That being said…

If I ever went back to Cuba, which is unlikely, I’d probably get out of Havana ASAP and head to:

-> Cienfuegos
-> Santiago

Both cities looking stunning and seemingly offer a unique look into Cuban life outside Havana.

If you want to get off the beaten path in Cuba, I’d start by heading to one of these cities.


Cuban food in Cuba is not good.

But it’s not as bad as some claim it is…

With a little effort, you can find a decent meal in the tourist areas.

I didn’t find a meal I “loved” during my whole time in the country, but everything was at least edible.

But the best meal of the day often was my breakfast from the casa particular host.


And while the food was mas o menos, the art scene was truly amazing.

I’ve never seen such spectacular paintings outside a museum in my life.

Some of the art for sell on the streets in Cuba is world-class.

If you walk along the center street near Parque Central during a weekend day, you will some truly beautiful artwork.

Artwork that would cost thousands of dollars back home, but is cheap as can be Cuba.


Oh, and speaking of unique art.

You absolutely must check out this club while in Havana:

  • Fabrica de Arte

Truly one of the coolest clubs I’ve ever been to in my life.

It’s a full-on art gallery mixed with disco.

Like blaring music and people dancing in one room, then full on art gallery in the next.

A must-visit if you’re in Cuba and want to enjoy some nightlife.

Check it out here.


In the club, the music from Drake to reggaeton to old-school rock. An odd mix.

But if there was one thing I learned…

Cubans love Drake. Like too much.

Plus, people actually dance and interact.

Oh, and the crowd is pretty mixed between tourists, Cubans, and hookers.


Speaking of that…

People actually talk to each other in this disco.

And all over Cuba. Everywhere.

Humans communicating with words.

While Cuba may be a shithole, you can’t claim that the ills of smartphone culture have hit the country.

No one in the club was using their phone.

No one in the streets uses their phone for anything but taking photos.

It’s refreshing in some ways. Probably one of my favorite things about the country.


Oh, and Cubans talk mad shit to each other.

You see people just chilling on the corner and talking trash all day and night.

Without WiFi and a decent paying job, many a person has nothing better to do than talk with their friends and neighbors all day and night.

While it’s sad in some ways, the lack of tech has ensured Cubans still have some modicum of social skills.


Now, what all you degenerates came for…

My take on the Cuban girls.

Overall, I’d say Cuban chicks are the hottest in the Caribbean. I certainly have love for the Dominican Republic, but Cuba might be a step up.

Even with their lack of money to invest in their looks.

Yet Cuba isn’t Colombia ;(

Sure, I saw some true stunners in the place.

Especially a couple of the girls wearing those state-sponsored uniforms in their airport.

Dios Mio.

But there’s an issue…


About 70-80% of the women in Cuba come with a “price” – if you know what I’m saying.

That’s not exactly my cup of tea, so I was less than enamored.

And everyone in Cuba openly acknowledges it.

Hell, this guy at the Cancun airport tried to sell me women while we waited for the flight.

My Airbnb host even brought up how much of an issue prostitution is in Cuba and I didn’t even bring up the topic.


And of course, we’ve gotta talk about the cars in Cuba.

Yes, it’s true. You’ll find classic cars everywhere in the country.

In fact, there are far more “classic” rides than newer models.

Some look damn good with fresh paint jobs, too.

Do they ride smooth? Not exactly.

While they keep these cars in decent shape, Cubans don’t have money to keep these cars in the type of shape they should be.

So they look great but ride awful.

More classic cars.


And the cigars?

Damn good. Overhyped, sure. But still…

You can’t go to Cuba and not smoke a puro, maricon.

Cohiba seems to be the biggest and most popular brands.

It’s run by the Cuban government, but then again…

So is every other Cuban cigar company in the country.

There’s no such thing as non-state-sponsored cigars sold in stores throughout Cuba, fam. We’re talking communism here.


My personal favorite is the Guantanemara, the is apparently produced in both Cuba and Miami.

They’re cheap but strong as hell.

Like you’ll get quite the buzz smoking one of these bad boys unless you’re a smoker.

I gave a couple to my buddies back in the States and they couldn’t stop raving about these puros.

Highly recommended.


One funny thing about Cuban cigars is how the government gets the tobacco to produce them.

They allow certain farmers to use the land to get crops.

Then when harvest comes, they take 90% of the crop from the farmers and pay them a “fair” price determined by the government.


Quote, unquote…

So, the farmers get to keep 10% of what they produce and then sell it how they see fit.

On the state-sponsored tobacco tour I went on, the guides made this sound like a great deal. Like it was a massive blessing to keep 10% of their crop. The crop they busted their ass for.

And I couldn’t help but laugh at this revelation.

The tour guide frowned.


Now, let’s get random…

If a Cuban is “hissing” to get your attention it’s best to just ignore them.

Hell, this could be applied to all Caribbean countries. Anywhere in the world. You don’t want to speak with someone that’s hissing at you.

Oh, and the girls saying, “Hi baby…” are not the ones you want, either.

Ignore these Cubanas like the plague, fam.


Don’t buy drugs in Cuba.

Seriously, just don’t do it.


Point. Blank. Period.

I heard some stories while chilling in Havana. There’s no such thing as a slap in the wrist in a communist shithole.


That being said…

Most of the cops generally ignore tourists in Cuba. Like the cops avoid eye contact just as many of the locals do.


Cubans want tourist money.

They want foreigners to have a great time in the country.

They don’t want one bad encounter with crooked cops to influence your opinion on the country. So most cops are taught to almost ignore travelers in their country.

You’d have to do something pretty grave to get bothered by the police here.


Cuba is a known salsa dancing destination around the world.

And there’s “shows” every evening showcasing some of the best dancers the country has to offer. I didn’t go, but many claim they’re quite the spectacle.

Plus, Cuban salsa music sounds much better than the Cali, Colombia version.

Gracias Dios.

As well, Cubans seem far more into hip-hop and reggaeton than Colombians. Which is ideal for someone who couldn’t stand any more salsa and vallenato.


Now, I’m no expert here.

But Cuban history, mixed with a little American interference is fascinating:

  • Cuban Missile Crisis
  • Bay of Pigs
  • Fidel, nationalism, and communism
  • Spanish American War
  • Even the JFK murder has a little Cuban flair

I read a whole tour guide from 2001 about the history of Cuba while in the country:


Cuba is only off-the-beaten-path for Americans. Gringos.

The country has more tourists than damn near anywhere else I’ve seen. It’s truly insane, especially in the tourist areas.

Thousands of Italians, Brits, Spaniards, Canadians, and Chinese come to Cuba every single day.

The airport is legit packed daily with international flights coming in every single hour.

It’s easy to see why…


I’ve alluded a bit to this already, but…

Apparently, Cubans can get in trouble with the police for harassing tourists.

So many people straight up ignore you when walking around gringo.

Like blatantly turn the other way to ensure it doesn’t seem like you’re interacting with them.

I’ve never experienced this in any other country.

In most Latin countries, people are interested in what you’re doing in their country.

Not in Cuba.

Although having so many tourists probably has some effect on that, too.


Overall, Cuba is interesting.

Fascinating in more ways than one.

It’s worth a 2-4 day trip just to see it. Cuba is unique, old-school, and stunning in many ways.

But I won’t be going back.

It’s a check it out one-time type of country. Nothing more, nothing less. Well, at least for me.


What else?

Rum is almost as cheap as bottled water.

Like retardedly close in price.

Getting drunk off cheap rum costs almost nothing in Cuba.

Havana Club is great, too.

A MUST-drink while traveling in Cuba.

High-quality Cuba rum.


In fact…

That may have been my favorite thing I did all trip.

Get hammered off a $3.80 USD bottle of rum and wander around the Malecon like a drunken gringo.

Highly recommended.



No one cares about you going to Cuba.

You can stamp your passport.

The ole’ USA will still let you in.

You will not have any issue with this. The United States doesn’t care. Cuba doesn’t care.

Just be yourself and enjoy your travels.


Not the best idea to talk politics in Cuba.

Consenting opinions are few and far between from what I’ve seen and heard. The lack of Internet has a lot to do with it.

You won’t get in any trouble, but you’ll find that the government has greater support than you’d ever imagine in the country.

A bit baffling, really.


Overall, the combination of:

  • Stunning architecture
  • Classic cars
  • Cuban cigars and rum
  • Nightlife
  • Beaches

…Makes a trip to Cuba more than worth it. Just come prepared.

This place is unlike anywhere you’ve ever been. A truly unique travel experience into a communist shithole.

Crumbling Havana, Cuba.

Traveling to Cuba: One Gringo’s Random Thoughts


That was a lot, y’all.

Over 4,000 words on a short trip to a small Caribbean nation. But here’s the thing…

I could talk about Cuba forever. The place is so unique that it truly blew my mind. Straight confusion combined with fascination.

If you’re a vagabond, make sure to check her out.

Traveling to Cuba is well worth the experience.

Oh, and join my email list down below if you’ve read this far:

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Jake Nomada

Travel junkie turned blogger. Location independent. From the Midwest, but often based in Latin America. Big on beaches, rumba, and rum. Addicted to the gym. Committed to showing a different style of travel - one that involves actually interacting with locals and exploring different cultures.

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