Cuba Travel: What it’s Really Like to Visit Havana as an American

By Sean Ogle •  Updated: 08/27/21 •  12 min read

I remember sitting at my desk years ago and writing out my bucket list.  It was a tough thing to do at the time, because so many of the goals seemed so far away.  I had no idea how I was going to accomplish most of the items with only 2 weeks of vacation time a year.

There was one goal in particular, that for some reason, seemed particularly unobtainable:

#47: “Go to Cuba before the embargo is lifted and have a cigar”.

Cuba travel just seemed so foreign, exotic, and unattainable. That’s part of what made the goal to visit Cuba so much fun.

Well, ladies and gentleman, I can now say that #47 is officially crossed off the list – and it was done in style.

However before I talk about the cigar, let’s back up and take a look at everything that led up to accomplishing one of the coolest bucket list goals yet.

How our Cuba Travel Journey Began

Six months before the trip, my buddy Nick told me about this idea he had for a gathering in Mexico that he was calling the Skip Winter Conference.  Seven days in paradise with a bunch of other really cool people? No brainer.

To make matters more interesting though, I read an article that talked about how Cancun was the major jumping-off point for Americans traveling to Cuba.

It was a totally casual half-serious question when I asked my buddy Derek if he had any interest in making a little jaunt over to the communist land.

“Cuba? Hell yeah!”, this was followed a few weeks later with an email from our mutual friend Clay saying:

“So, I’m not trying to invite myself along, but um, I’m totally trying to invite myself along.”

This led to booking our overpriced tickets from Cancun and we were on our way.

Cuba Travel: In Transit

When waiting to check-in for a flight to Cuba you start playing a little game, called “Guess the other Americans”.

Even though thousands of people go illegally every year with no issues, my heart was still racing at a few key points throughout the trip.  However, after seeing no less than a dozen other American passports my mind was temporarily put at ease.

The 51-minute flight into Havana was relatively uneventful, but upon landing it was clear that we definitely weren’t in the US anymore.

Looking out the window the first thing I see was an undead Amy Winehouse look-a-like with full beehive hair and patterned black nylons tossing bags onto the trolley.  Working with her were dudes at least three times the size of me who each had approximately 17 zippers on their jeans – I didn’t know that was possible. Fashion in Cuba is its own beast.

Going through immigration, customs, and getting money changed was just as fascinating.  The women were beautiful and each had a very unique style that you just typically don’t see with transportation workers.

We ended up hopping in a car with a very sketchy-looking local woman who promised to take us to our Casa Particular.  You see in Cuba, it’s not like you can just call up a friend and invite them to stay with you for a week.  Rather, you have to apply for a license to be able to house foreigners.  Everyone seems know someone who runs one, and everyone is trying to get a little commission of their own.

This was best evidenced by the fact by the woman at the information desk in the airport.  We asked where we should stay and her response was “at my friend’s castle!”.

Skeptical, we agreed.  However, upon arriving, we were pleased to see that she had in fact not been lying – the place was spectacular.

One thing to note about Cuba is that you can tell at one point in time, this was the spot. I would have loved to see this place in it’s heyday during the 40’s.  The architecture is beautiful, and while the country is quite clean, there are certainly many areas that are a bit worn.

Courtyard of a house in Havana, Cuba

The courtyard of our abode in Havana

Within 5 minutes of arriving, our host Acello had poured us some of his finest Havana Club Rum, was on the phone finding us cigars, and had his family preparing us a lobster dinner. Oh, and did we mention the room was only $10/night each?

This is living.

After dinner and a couple cuba libres, we were dismayed to find out the cigars would have to wait, so we went out for an evening stroll through our neighborhood of Havana Vedado.  By this time it was close to midnight, and the streets were PACKED.  Havana is a lively city at any time of day, and even though most were just grabbing ice cream or pizza at the local corner, there were undoubtedly a lot of people around.

A Tour of Havana

The following morning we set out with one goal in mind to experience as much of Havana as possible.  Oh, and drink mojitos and smoke cigars.  Ok, so maybe it was more like three goals.

Within minutes of seeing the city in daylight, one thing was abundantly clear about the people here: they were proud of what they had.  Whether it was the incredible pre-embargo era cars, the way they dressed, or the condition they kept their homes, the Cuban people are very proud of their country.

Old Car in Havana, Cuba

This was one of my favorite photos of the trip.

We spent the day crisscrossing the entire city and it seemed around every corner there was something new and exciting.

It didn’t take long to realize that our trip was beginning to have a lot of repetition to it.  In fact, we pretty much did the same 5 things over and over again for 3 days:

And you know what? I wouldn’t have had it any other way.

Cuban Food and Restaurants

One of the things I was most excited for about Cuba was the food.  I knew little about it, but it’s always had this allure to me that I was excited to explore.

The reality of Cuban food? It didn’t quite live up to expectations.  

While there were certainly some great meals and incredible flavors at times, on the whole we found the food to be relatively bland.

That said, the value and experience of eating in Cuba is second to none.  I can vouch for Chris Guillebeau’s observation that there is live music everywhere in Cuba.  As he put it “There is no Burger King in Havana, but if there were, I’m sure it would have a full salsa band at the entrance as customers ordered their Whoppers.”.  This made every meal a great time, even if the food wasn’t always the best.

The value of the food on the other hand, is huge.  For instance one evening we decided to have a nice meal.  We went to a place that looked like a 5 star restaurant from a major metropolitan city (a lot of places felt like this) and treated ourselves to a nice four course meal of steak and lobster.  Total cost? About $15 with a couple cocktails and tip.  Was it the best steak of my life? Nope.  Was it passable given the price? Absolutely – and then some.

The Mojito

In similar fashion to my trip to Brazil a few years back where I tried to search out the best Caipirinha in Rio, I had a similar goal to find the best mojito in Havana.  Pretty much anywhere you go you can find a Mojito for 3 bucks.  Havana Club is everywhere and it seems to be the only thing locals drink.

Having a mojito in Havana, Cuba

Our first, ok third, Mojito in Havana

That said, I sampled 3 or 4 different variations of the rum, and I must say each was fantastic – and incredibly cheap. At the store a bottle of 7 year aged rum costs about 8 bucks, $3 if you want the basic light rum.

Also, the mojitos in Cuba are different than the ones you’ve probably had elsewhere.  They are very strong, the mint is not muddled, and the sugar tends to kick it on the bottom of the class. We weren’t sure what to make of it at first, but in the end it definitely grows on you.

Generally speaking, alcohol is surprisingly affordable here.  You could get a 2oz pour of Jameson for about 3 bucks at many places, and even get a glass of Jack Daniels for the same price (what embargo?).

The Cuban Cigar

Without a doubt, this was one aspect of Cuba that I was very excited for.  Not that I’m a huge cigar fiend, but the bucket list goal clearly stated that I had to smoke a cigar, so I couldn’t cross it off the list until I’d done so – that said, this goal was accomplished in probably the most appropriate and awesome fashion possible.

Derek Johanson, Clay Boeschen and Sean Ogle at Hotel Ambos Mundos in Havana, Cuba

Derek Johanson, Clay Boeschen and Sean Ogle at Hotel Ambos Mundos in Havana, Cuba

It was the middle of the afternoon during our first full day in Havana and we’d finally stumbled into Havana Vieja (Old Havana).  We’d had our fair share of mojitos and meals at this point, but still hadn’t been able to find a fitting spot for that first cigar.

Then we walked into Hotel Ambos Mundos.  This is one of the older more classic hotels in the area, and it’s actually where Ernest Hemmingway wrote the book “For Whom the Bell Tolls”.

The more I learn about Hemmingway the more I realize I think we would have gotten along really well – so to sit in the lobby of the hotel and have a cigar seemed pretty appropriate.

Now, I’ve had Cuban cigars a couple times in my life.  The most notable of which was a Cohiba Robusto that my dad picked up at a duty free shop in Switzerland.  The cost? $80 for 3.  That said, it may have been the only time in my life where I could legitimately say “Damn, thats a good cigar.”

A couple Cuban Cohibas at Hotel Ambos Mundos

The Cuban Cohiba

Now that we were in Cuba, regardless of the price I couldn’t cheap out and get something mediocre, so I browsed the menu and found the same one.  This time instead of being close to $30 each, they were closer to $5.


We sat for the better part of two hours drinking the local Cristal Beer (which was surprisingly good), smoking our Cohibas and pretending like we’d been transported 60 years back in time – as at that moment, it felt like we were.

We smoked a few more cigars on that trip, and almost bought a box to take back to Mexico with us to enjoy during the remainder of our time there.  Would have been a good idea considering the same cigars there were $40 each in Playa del Carmen.

Overall Impression of Havana

At the end of our three days in Havana we all agreed that no matter what fine was incurred as a result of traveling here, it would be well worth it.  Cuba is one of the few places I’ve ever been where I felt like I was truly living in a different era.

The capital building in Havana, Cuba

The Capital Building in Havana Vieja

The people were extremely friendly, the architecture (as you can tell from the pictures) was unbelievable, and the sense of adventure you get from going someplace forbidden made this one of the most rewarding trips I’ve ever taken.

If you every have the opportunity to go, I can’t recommend it highly enough, and in fact, I’d suggest you do it sooner rather than later.  I can’t imagine what Cuba will be like when the embargo is lifted, but I’m sure it will be a very different place than what we experienced last week.

Old Buildings in Havana Vieja

Old Buildings in Havana Vieja

Coming Back from Cuba

Coming back into Cancun from Havana was a relatively painless experience, made even less painless by the fact that somehow we ended up in first class.  Yep, the first time I’ve ever flown up in the front of the plane and it was on a 51 minute Cubana Air flight – which may win awards for worst first-class experience ever (I couldn’t even buy a beer, although they did have free rum).

The stress-free trip would soon however be interrupted by a momentary feeling of terror upon going through immigration back in Mexico.  While they will never stamp your passport in Cuba, my biggest concern was having the double-entry stamp in my passport.  I figured it wouldn’t be a big deal as long as they were on separate pages, so I asked the officer if he would find doing that.

Well, I must have said something to piss him off, as I ended up with both of my Mexico stamps side by side on a blank page.

Sweet. I spent the next week going through scenarios of what I would say when asked about the double stamp, and alas it was all for naught as an hour ago a half-asleep customs agent whisked me through with hardly a glance through the stamps.

So did Cuba meet expectations? Exceeded

Would I go again? In a heartbeat.

Should you go? As soon as possible.

Have any plans to go to Cuba or have you been there yourself?

I’d love to hear your stories as it seems like everyone’s experience there is very different. Have any questions about travel there?  Just leave a comment and I’ll do my best to answer.

Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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