Oriente Cuba: 7 Obversations We Learned


Last week, Yoel and I embarked on an adventure of a lifetime– traveling to Oriente Cuba.  Neither of us had traveled beyond what I call the “tourist golden road” of Trinidad / Santa Clara. And what I found there changed many perspectives I have of the place we call home. 

Often when people suffer from “culture shock” it’s because they went to another country.   Imagine experiencing that in your own country.

That was Oriente. 

So let me explain some observations I took away from traveling cross country and seeing our island beyond what we thought we would ever see.

1. Oriente Cuba is more beautiful than what I Thought

Cuba block sign on Santiago’s malecon

To be honest, much of the landscape between Santa Clara and Santiago de Cuba is flat. Nothing much to see in terms of beautiful picturesque island-scapes. But let me tell you, once you get to Santiago de Cuba and from what appears out of nowhere giant mountains pressed up next to the sea it will take your breath away.  

2. We don’t understand now why Oriente, Cuba lacks tourism 

Oriente, in particular, Santiago de Cuba, is a tourist dream. Its a beautiful city pressed along the ocean with many activities both beach and nature around. The city itself is impressive, CLEAN, and filled with restaurants bars and shops.  

 In the 3 days we were there, we both noticed that everything was always on the menu. We never heard the dreaded “no, no temenos eso (no we don’t have that today)” as we often hear in Havana. 

Infrasture wise, the streets were lit, the streets without potholes, and signs everywhere telling people where attractions were. 

It just left us incredibly impressed. Were we still in Cuba?   How did Havana, with its trash lack of resources and broken infrastructure become Cuba’s tourist destination? 

But  why does Santiago have better and more things? That leads me to the 3rd observation 

3. If Someone Important lives there, its nice. 

It didn’t take long to realize that the reason Santiago de Cuba looks like a mini-Europe is because the most important family is from and still currently lives in Santiago. 

Outside of main cities like Santiago or Camaguey (camaguey was recognized as a UNESCO world heritage site, therefore maintained much nicer) infrastructure needs, lack of opportunity, general poverty was pretty noticeable. 

Granma is cited as the poorest provience in Cuba and we definitely noticed it. Which takes me to observation #4 

4. Theres millions of people in Cuba who do nothing all day. 

At every place we stayed at (Santa Clara, Santi Spiritu, Cienfugos, Camaguey, Holguin, and Santiago de Cuba), there were mass amounts of people who do nothing all day.   This isn’t that new to us as we see it everyday on the street corner in Pinar del Rio, but seeing it across the nation is pretty astonishing. 

At one point Yoel and I asked a bunch of 20-30year olds if they knew where the woman who was supposed to be working at the gas station (Cupet) was. They said “probably at home, theres nothing to do here.” 

I asked them if they had jobs and they all answered what most Cubans answer “inventando” or “inventing”.  In Cuba, inventando is doing odd jobs here and there to make ends meat.   They are not hired directly but rather just find little things to do maybe 3 times a week to make a bit of money. 

I couldn’t help but think that if entrepreneurs were supported, uplifted, and encouraged in Cuba many of those same boys could be employed by new jobs. 

As well with the drunks.

5. Cuba’s alcohol problem stretches across Oriente Cuba 

I couldn’t tell you how many times we came across drunks during our travels.  They seemed to be everywhere.  Again, something we are used to in Pinar but we never really thought beyond to the entire nation. 

In Cuba, there is AA but the culture to get sobered is not promoted nor enforced in society as much as you see in others. 

The problem got to be personal when Yoel and I fought over him giving a drunk a dollar when we was peddling – an action I cannot participate in.

 6. Pinar del Rio is the worst provience capitol in Cuba 

We stopped in every single provience capitol with the exception of Guantanamo and it’s a fact- Pinar del Rio is the worst one. 

In Cuba, the rumor of Pinar del Rio being the worst provience always existed since before and after the revolution.  

Despite its huge tourism coming for Vinales and Maria la Gorda, Pinar del Rio (the provience capitol city) lacks major infastrucutre, attractions, culture and general cleanliness. 

Let me give you an example: Every provience has plaza’s, a shopping center (bouvelard), several museums and art galleries.  Pinar del Rio has 0 plazas, 0 shopping center, 2 museums (one of which is in repair for years), and 1 private art gallery. That’s it. 

Pinar del Rio’s roads are in horrible shape inside the city and its buildings in dire need of repair. 

We constantly compared Oriente Cuba to our own city and we couldn’t help feel sad and shameful that Pinar continues to be the what we think, the worst one.

 7. Not every Cuban can travel to Oriente Cuba and we know it

The economy and the tight wallets get in the way of many Cubans traveling inside their own country. They are so desperate to leave to see the world they forget to see their own.  

We traveled across Cuba in motorcycle and it was the best and most economical way to see Cuba on our own terms. 

The entire time we felt blessed we were able to have an opportunity that most never get in a lifetime. And we cant wait to do it overagain… Maybe this time…WITH YOU! 

kisses at Holguíns loma
Family and dog on the couch

5 Tips to Dating a Cuban – You’ve been Warned!

Let me guess. You went to Cuba for a long weekend and met a seemingly mysterious and charming local at Fabrica del Arte or at some other paladar in with live music. One kiss and exchange of social media handles later and you’re officially in a relationship. Welcome to Dating a Cuban.

Cubans are notorious for their charm and their confidence to show you it.  We don’t blame you for falling in lust in a weekend. No one does, not even Camila Caballo in her famous “Havana” hit song.

But, I hate to break it to you, you aren’t alone.

If I had a dollar every time someone messaged me (on Instagram) a version of that story, I could buy an overly priced motorcycle already on this damn island.

Dating a cuban and the love culture in general here is hard to explain and even more complicated to understand. Though, anyone who’s spent significant time here knows what I’m talking about.

In some unspoken language, we all do. We all know what’s happening and we all keep our mouths shut. I mean, after all, it isn’t our business. But I’m willing to share a few observations I’ve learned over the years.

So before you recharge a cell-phone or send any money through Western Union, let me try my best to describe and give you some tips on how things work here on the island of lust.

And by no means is this a blanket explanation of every Cuban-foreign relationship. I myself would be a hypocrite to state that, as I am a Cuban-American engaged to a Cuban-Russian born (its complicated…).

So no, this does not apply to everyone. But it does, indeed, apply.

Two cuban women in traditional wear kiss a foreigner on the cheek.
The Warm Up!

1. Cuba’s Bad Economy Creates Avenues of Desperation

First things first: Cuba’s economy. It’s no surprise to anyone that Cuba isn’t exactly experiencing its “Golden” age.

With wages low and opportunities even lower, for many the Cuban dream no longer is a dream inside the country.

Cubans look north. They look south. East and west. Just about anywhere but Cuba for their dreams for a better future.

It’s something everyone here seems to have in common. It unites the country in some bizarre melancholy way and everyone talks about it. It’s the social glue that bonds us all together.  

And because of this, Cubans have tried various different methods to leave the island or make their situation on it much more comfortable.

That’s where you come in.

2. Dating a Cuban 101: Jineteros

Text Jineteros en Cuba a cuban man and foreign woman on a balcony. Faces covered.
Cuban Jintereos : Dating a Cuban

To the seemingly naïve foreigner, many don’t know what a “Jinetero” is. Though, in Cuban culture, ‘jinetero” is a term we grow up with.

Jineteros or Jineteras in the simpliest form are hustlers in any way but most known for being in the sex industry. Whether for a day, a week, or for an entire relationship.

Yes, I said it- an entire relationship.

We have met some jineteros that will fake being in love to continue an ongoing relationship with a foreigner. It’s a sad truth, but it does happen. They will have their own families on the island and when the foreigner comes, their partner vacates the home and the rest of the family plays along.  They work together for the week.

Of course, like I said not every relationship is this way but if you expect to be dating a Cuban you will absolutely have to know what a jinetero is.

3. It will Be an Expensive Relationship

Expect to pay…. For everything.  Unfortunately, few Cubans have the money to take their partners on a proper date to wine and dine them.  That shit doesn’t happen here. 

If you’re used to your partners taking you different places and having them pay or sharing costs, this will definitely test you.

Because besides the costs of going out to dinner and dates, you will have to get to Cuba and most likely gift them things they and their family needs. Oh yes, the. Family is always included in Cuba. Always.

The real costs are maintaining the relationship.  Want to call Cuba? EXPENSIVE AF

Want to talk to them on the internet? EXPENSIVE AF

Want them to leave the country with you to start your life together? SUPER SUPER SUPER EXPENSIVE AFFF FOR YEARS.

But if they are worth it, then you won’t care. Here are some apps you’ll need in Cuba.

Man and Woman chatting on a videocall. Dating in Cuba
Yoel and I chatting on FaceBook Messenger

4. Cubans Cheat… A Lot

I know this is particularly hard and uncomfortable point to write, but they likelihood of your Cuban cheating on you while you’re not in Cuba is enormous.  Whether you’re okay with it or not, its really apart of the culture.

And weirdly because its so prevalent its still taboo to talk about.  Its like we all know its happening but pretending its not.

Ojos que no ven, Corazon que no siente (Eyes that do not see, heart that does not feel).

Really though: Cubans cheat and they do often.

When there’s nothing to do all day and the culture very open with sex in general, the field is wide open. Plus its also very hard to find out what you’re partner is doing inside the low connected island all day.

I recommend having an honest talk with yourself and your partner about what you expect and your values.

5. Dating a Cuban = Moving Incredibly Fast

I’m laughing writing this point up but here’s a typical storyline:

  • Day 1: You meet and have fun
  • Day 2: You Meet the Family
  • Day 3: The Proposal

Ok that’s a bit of an exaggeration, but true. Cubans date insanely fast compared to foreigners.

For example, foreigners take months to decide if they are actually in a relationship or not, Cubans are moved into their in-laws in a month, have a ring, and call each other “maridos (husband/wife). 

I’m serious.

In conclusion, don’t be weirded out (and I am warning you) If you get proposed to on your 3rd or 4th visit and already having their mom calling you her son or daughter in law.

If you think its going too fast, just try to explain to your partner how things are a bit faster than what you are used to. Don’t feel pressured into things if your gut is telling you something else.

Boys in a cuban neighborhood
Your new family isn’t just you in-laws… its the entire neighborhood too.


If you’re traveling to Cuba as a female solo or in a group, please please read my tips on female travel in Cuba. In short, Cuba is a fun and extremely safe place for females. You’ll just get lots of catcalls! 🙂

Catching a Cuban eye is very very (extremely) easy to do, but knowing what to expect is hard.  They will charm the shit out of you but you have to be careful who really has good intentions, as in any relationship, with anyone, from anywhere.

Many Cuban-Foreign relationships are very beautiful and we know many long -lasting ones so of course take this blog with just precaution.

All I ask is that if he or she is constantly asking for money or material items to do a hard look. I advise strongly against be sending large amounts of money on the regular to your Cuban boo.

In other words, have fun and be safe!

If you need help planning, as always let us know!

EXPLAINED: Cuba Legal Travel After Trump in 2019

Cuba Legal Travel is still possible!

Cuba Legal Travel just got a bit more complicated. After Trump rolled back on travel liberations made by the Obama Administration, he cut off not only “people-to-people” visa category but now the group educational category that affects largely cruise ships.

But, No Need to Fear! Cuba Legal Travel is still here!

Trump might have disrupted cruisers (honestly, why would you come to an amazing place like Cuba on a ship for less than 24 hours I will never get) but the travel restriction did not affect flights

And most importantly….

It did not take away the “Support the Cuban People” visa category.


Well before we start, it is important to note that Cuba does NOT have an embargo against the United States. Regardless of what passport you carry or what country (if you come from a third country i.e. Cancun to Havana) in from, Cuba will welcome you with open arms, café, and most likely dance lessons.

Under current 31 CFR 515.560 law, Americans can use one of 12 reasons to enter the Cuba, one of those being Support of the Cuban People, Provision found in § 515.574 of the CACR, US government.

It defines the visa as activities are recognized human rights organization, independent organizations designed to promote democracy or individual’s organization that promote independent activity intendent to strengthen civil society in Cuba. Provision § 515.574(A) to this means the traveler must have a log of their itinerary for up to 5 years.

In English?

It means this visa has to record that you kept a full schedule seeing individuals or organization that directly help or show Cuban society.

You can’t you use your bank card to it, as that evidence against “supporting the Cuban people”..

But this visa category is extremely vague.  The OFAC does not or will have a list of such organizations or individuals that promote “democracy” or “civil society” in Cuba.  Nor can the OFAC track your cash money on the island.

What you need to do to fall under this category?

Like all categories, you must have a log of your itinerary for up to 5 years (501.601).  It also means that itinerary has to show at least 8 hours of cultural experience. You do NOT need to have an itinerary prepared before you go, but if you want I got you!

I offer customized Itineraries that Comply with Support the Cuban People

Itineraries of such activities can include several tourist experiences.

  1. Curating a local tour with a local guide
  2. Eating at a local paladar (restaurant) can be considered “support of the Cuban people”
  3. Buying Cigars from a cigar farm directly from the farmer, not the government
  4. Classic Car Tours with Private car owners!
  5. Taking a class at a private owned business like salsa dancing, mojito class, afro-cuban history, cuban history, cooking class, ETC! so Much!
  6. Staying at a local casa particular, found on Airbnb!
  7. MANY MORE!!!
Cuba LEgal Travel, girls sitting having cuban lunch at our family home
Cuba Legal Travel includes having lunch at my families home!!

How Do I get My Support the Cuban People Visa? Mari, Help!

When you book your flight to Cuba you will be warned on all airline websites. Check the box that says Support of the Cuban people (if prompted to do so, some airlines don’t even have you do this rather just put the warning).

When you get to the airport, check-in will ask you the purpose of your travel. You simply state “Support of the Cuban People.” If they ask you for an itinerary and you don’t have one, you simply state you didn’t produce a hard copy. Or, you can have me customize one for you 😉

After that, all you have to do is buy the visa right at the gate or check in. Remember, Cuba does not have an embargo on the US so Americans are welcomes with open arms in Cuba.


When you come back to the US, it is very rare you will asked further questions besides “what did you bring” question at Immigration. And if you do, if you followed your itinerary, you have nothing to worry about!!

And remember, Cubba is cash-only and totally guilt-free.

So please don’t let the travel ban stop you from visiting this INCREDIBLE ISLAND!

Women in red dress standing in front of the Cuban Flag Mural in an abandoned building
Travel to Cuba is still legal and enjoyable! Don’t let politics get in the way of an amazing vacation!

Cuba Tornado: How to Help and Donations to Give

Cuba Tornado Donations and how you can help: On January 27th around 9:30pm, Havana’s outside neighborhoods were struck by an extremely rare powerful and devastating tornado.

The rare weather accident has put thousands without homes, electricity, running water, or food since the incident occurred. It has affected large areas of Regla, Guanabacoa, 10 de Octubre, and Santo Suarez neighborhoods.

Its no secret that Cuba has been facing economic struggles for the past 30 years. Those woes combined with a horrible tornado and structures that were poorly built have been toppled and infrastructure already too old, washed away.

But there are many ways you can help the Cuba Tornado Disaster. Here are some below

Donate to a GoFundMe Page who’s already on the ground in Cuba.

I have set up a gofundme page that will get food on the ground to these neighborhoods. Link here. 

We will be donating food for now. Construction materials are very hard to find here and the most needed is food and water. We will be using the money for that.

Bags that are being donated to the tornado relief

Bring Items For Those in Need

If you are on your way to Cuba, PLEASE use the extra space in your luggage (or bring a check-in) to bring supplies that are NEEDED and very very hard to find in Cuba.

Those items can be found on my page – These items never go out of style to donate to Cubans. ANYTHING IS APPRECIATED.

If you do come, please contact me and I will distribute the best way possible to affected families.

In Cuba? Donate to FAC

If you already in Cuba or coming soon but don’t know where else to donate, you can donate to Fabrica del Arte (on Calle 26 y 11) who is collecting items and sending groups to affected areas. They are accepting clothes and food as of now.

Send Hot Food to Family and Friends in Havana!

The food start-up, A La Mesa, is eliminating their service fees and taking 15% off all orders that send hot food from a Cuban restaurant directly to your loved ones in Havana.

They are doing this promotion until 4th of February.

Finally Uber in Cuba? The New Revolutionary App

Is Uber finally in Cuba?

No, but with its own twist of Cubaneo, “SUBE” is. With the arrival of 3g technology and a group of millennials who’s office is a WiFi Park, Sube Cuba is officially the country’s first ride sharing app! 

And to that I say: Hallelujah! 

The app came just in time. The Transportation Issue.

New constitutional provisions that prohibited many private taxis to operate was introduced around the same time mobile data was announced to the public.  

But before these changes were happening, the group of 4 20-something’s were already trying to solve an endless problem Cubans are confronted with everyday: transportation. 

That problem has been a major issue in this county for decades. The combination of the US embargo alongside domestic economic and political issues has damaged public transportation and the buy and sell of vehicles. 

This is especially true in Havana, Cuba’s capital.  With a population of 2 million people, the bus system is minimal and leaves many riders jam packed (unsafely I might add) in busses. 

Now with the new constitution crusading against unlicensed (untaxed) private taxi drivers, the problem got exponentially worse. 

Before, Many Cubans use “colectivos” as an option of public transportation. These private cars pick people up on a certain route and drop them off for a set price (usually around 10 pesos cubanos or 50 cents cuc per person).

Now after the provision, taxi drivers are required to have a license from the state, pay monthly taxes, forced to buy a quota of state gasoline (previously bought more frequently on the black market), and mandated to lower the prices of their services at the same time. 

So it’s only natural to know what comes next: very little taxis. 

That’s where Sube comes in. Before the announcement of mobile data, the group was already implementing the app via email service. But once the mobile data services were announced, it changed the entire game. 

How SUBE is Changing the Game

With Sube, Cubans and tourists can now upload the app and ask for direct taxis. Drivers have the option to charge their prices and accept rides. 

It works similar to Uber though not as advanced. There’s no “uber pool” or options of cars. 

But it resolves many issues people face on the island. Now with just an app you can have your ride waiting for you without standing on the corner forever. 

The app is completely free to download and use for both the rider and the taxi. 

Uber in Cuba: Sube Cuban app
Sube Cuba platform

An App with 0 Funding

The founders, Claudia, Darien, Damian,  and Luis Alberto sit in the WiFi Park everyday coding and designing the app. They have yet to monetize the app (a very legally tricky thing to in Cuba) so they make absolutely no money off creating the app. 

As of now they are just trying to perfect the app so it works perfectly and get the word out. They have about 3,000 users and the number is rising everyday. 

Claudia hopes that the app “resolves both Cuban problems and tourists problems.

Tourist App

Many times as a tourist you don’t know how much transportation is and you get ripped off just because you’re a tourist”. With the app, the price is confirmed before hand without the driver knowing country of origin a rider is from. 

Transportation is already tricky for tourist. But with Sube this makes it even better!

The app is only available through Android but they are quickly working on releasing it for iPhone. 

Just another amazing story of Cuban strength despite the technological and financial challenges. 

While many news publications will compare Sube to Uber, perhaps Uber might learn something from a group of four techies in a country where tech is far from modern. 

You can download Sube here and check out their Instagram and Website