How Americans Can Travel to Cuba Without a Group in 2019

My family and I at the Hotel Nacional de Cuba which is one a the few government run hotels that the American government allows us to stay in.

My family and I on Christmas Day 2018 at the Hotel Nacional de Cuba in Havana. This is one of a very few government run hotels that the American government allows Americans to stay in.


I’m writing this from the Plaza Hotel in Havana. I’m here with my family celebrating the Christmas holidays. We were supposed to have been on a Royal Caribbean Cruise because we believed that individuals couldn’t go to Cuba alone, without being part of a pre-planned group.

Through a series of errors and miscommunication we weren’t able to take that cruise, but those problems are for another, longer post.

What appeared to be a huge problem, causing us to lose all of the money we paid for the cruise ended up being the BEST THING THAT COULD HAVE HAPPENED!

Here’s why. We discovered that it’s easy for individuals to travel to Cuba alone and we’re having a fantastic time! Much, much better than we would have had on the very limited and poorly managed Royal Caribbean Cruise.

Our Vacation Overview

We’re staying at an AirBnB that our adult son found. I’ll write more about how fabulous that’s been later…but for now I just wanted to share where, in case others are interested right now. Below is a screenshot of where we’re staying.

This is our host's marketing pamphlet. You can book all of his rooms using  a variety of methods. Either directly by emailing him, or through AirBnB or
This is our host’s marketing pamphlet. You can book all of his rooms using a variety of methods. Either directly by emailing him, or through AirBnB or

How to get to Cuba the Fastest, Easiest Way Possible

The key to getting here is getting a Visa, which you do via American Airlines. You don’t need to actually fly using American…but you do need to fly through the Miami airport.

You buy a ticket to say, Havana, via Miami. Once in Miami you need to leave your concourse and go to American Airlines ticket counter #7. There’s a little booth that’s sort of surrounded by American Airline’s kiosks, which has one or two officials standing there waiting to sell you a Visa. The cost is $100 and they will only sell you one if you already have your flight booked and can produce your boarding pass for them to stamp. If it’s an American boarding pass they will have already asked you at the ticket counter why you’re traveling to Cuba.

I won’t go over the 12 possible reasons because many other sites have covered that. We were advised that the best, and perhaps only reason to use is this:

“In Support of the Cuban People”

When the American Airline’s ticket agent asked us that question she included our answer within our digital travel record. So all we needed to do was present our boarding pass, pay $100 per person and get our boarding pass stamped. Then we were on our way!

I’m Not Sure of the Process for Other Airlines

I suspect that you may need to fill out some kind of form. What I am sure of is that regardless of the airline you’re flying on, you are able to procure your Visa this way. It’s instantaneous and so much easier than the longer, more typical method of going through the Cuban Embassy.

*Since we’ve arrived back in the states and have internet again (we’re in Miami currently for our last few days of vacation) I’ve finally been able to do a little more research regarding flights.

We met several other American families who were also traveling independently while in Cuba. We discovered that there are more alternatives available than we’d realized. See below under the ‘After Thoughts‘ section at the end for more information.

Our Arrival in Cuba

Once you arrive in Cuba you will need to present the Customs Officials with 2 forms. One appears to be a generic one that just reiterates the details and of your airline reservation. The other is a health form that supposedly is needed for arrival…but no one actually was asked to produce this in Cuba. We did walk past several tables with signs that appeared to be for this purpose during our arrival, but everyone on our flight was just waved through.

We were told that customs would tear off 1/2 of the generic looking form…because it repeats your flight information on both sides…but again, no one did. Later, upon closer inspection, we figured out that this document was actually our Visa. We were told the duplicate section would be torn off when we left Cuba. That did happen for all family members except me. I don’t know if they forgot or what…but no one tore mine off.

At one point during our arrival we did talk to a Customs agent too but no one remembers that conversation…it was unremarkable. The whole time we were half expecting someone to stop us and tell us that we had to turn around and fly back to the states…because we weren’t allowed to come as a private party with no organized entity behind us…but that never happened.

One reason we were so sure that we wouldn’t be allowed into the country was because several Royal Caribbean employees had told us that. We’d been told that we couldn’t fly there when we asked about boarding the ship in Havana. We were also told that if we somehow managed to make it there, we wouldn’t be allowed to board the ship because “Royal Caribbean didn’t have the appropriate ‘intake’ personnel onboard the ship.”

When we walked out into the main, open part of the airport, we breathed a sigh of relief, found our luggage, got a cab and proceeded on to our AirBnB. Even our son who booked the AirBnB didn’t really know what to expect. As we approached the somewhat rundown looking building in the even more rundown looking neighborhood, he said “Mom and Dad, if this doesn’t work out we can look for a hotel in the morning.” We were all pleasantly surprised when we received the warmest welcome we could have possibly imagined. Our accommodations, while sparse in comparison to US standards were more than adequate for our weeks’ stay. The hospitality more than made up for any slight inconvenience we might experience in the following days.

More About AirBnB’s in Cuba

I intend to (and will hopefully follow through) with writing much more about our AirBnB and ‘traveling to Cuba’ experience since it appears that there’s significant confusion amongst Americans about these aspects. We didn’t get all the answers while there, but we feel that our experiences combined with a significant amount of research once we were back in the states will help to shed light on many of the misconceptions most Americans currently hold.

Misconceptions like, that Americans need to be part of a group that participates each day in a full day’s complement of strict and narrowly focused activities in order to comply with some vague, oft-repeated but never documented ‘law’ that states this. I’ve searched high and low for days for any documentation like this…it simply didn’t seem to exist beyond the confines of the writing at many of the websites offering group paid tours and cruise lines offering pricey itinerary’s that comply.

At one point in time we believed that much of the misinformation that’s flooding the internet regarding American’s traveling to Cuba was fabricated by the companies who are profiting handsomely from it. But we now know that isn’t true because we were finally able to read a copy of the entire set of laws and restrictions, which I’m including here too.


A Little Information About Our AirBnB Experiences

In the meantime I just want to say a few things about using AirBnB in Cuba and about our experiences.

  • First, we were pretty shocked to find that AirBnB’s even exist in Cuba…because it’s an American company. The hoops that Cubans have to jump through to be on AirBnB are considerable, but we found that there is a great number and variety of choices using them.
  • Most AirBnB’s in Cuba fall into one specific category of accommodation called casa particulares…which are essentially Cuban bed and breakfasts (although a true vacation rental can also fall into this category.) If there’s any truth to any of the current stated restrictions upon Americans then staying in a casa particular or a private rental is by far the best way to connect with Cuban people during your stay. The long, heartfelt conversations we shared with out host, his family and friends educated us far better than some organized educational group experiences ever could. Alongside our hosts, we shared (and ‘lived’) their experiences with the overwhelming number of product shortages that fulfill so many of people’s basic daily needs. We were equally frustrated when our brilliant ideas to address problems their businesses face were shot down, one after another, because of their unique circumstances.
  • It would be difficult to overstate how much better our experience was because of our accommodation choice. Eddy, the main proprietor of Dom Pepons, our casa particulare is AMAZING!!! He welcomed us with open arms into his family and they all made us feel like a part of their family too. Btw…Dom Pepon was the name of Eddy’s deceased grandfather.
Our room at Don Pepons
Our room at Don Pepons
  • Our accommodations included 2 rooms with 2 twin beds…both with en-suite bathrooms and some of the best air-conditioning units we’ve ever experienced while traveling!
  • Was everything perfect with our rooms? Not necessarily…but this was through no fault of Eddy’s. It’s because so few of the basic needs that we so heavily rely upon are even available there. Those that are available oftentimes require significant effort to procure. Eddy bent over backwards, as did his family, (his family is primarily his staff,) to fulfill our every need and request.
  • We were provided with meals upon request and given several meals just because. Our first morning’s breakfast and Christmas night dinner were superb and ‘on the house.’ In fact, Eddy invited us into his own home on the floor above us to dine with his family for Christmas dinner…and he did all the cooking himself! This was the night we arrived and our only regret was that we were all too exhausted to stay up late and enjoy all of their festivities. The mental strain of the last 24 hours finally overtook all 4 of us once we were safely and comfortably ensconced within Eddy’s wonderful home.
  • One kind of humorous note is that we asked for a box of Kleenex in our bathrooms. Our request was met with a blank look. The next day while on a previously booked ‘Overview of Havana’ tour, I asked our tour guide because his English was flawless. I did it at a point during the tour when we’d arrived at what we were told was the largest shopping ‘mall’ on the island. Using the word ‘Mall’ was a bit of an overstatement! I asked our guide if I could try to find some Kleenex. He too just looked at me with a blankness that indicated to me he had no idea what I was talking about. I tried to explain…but he truly was confused by my question. In the end I got my answer when I asked him what he used when he wanted to blow his nose. A look of enlightment spread across his face. He finally knew what I meant and he told me they just use toilet paper for that. Later in the week I talked to another family staying at one of the very expensive government run hotels (expensive because of all the additional charges that were tacked on at the end.) I was surprised to discover that they did have a small box of Kleenex in their bathroom. We decided together that their Kleenex was probably added just for the comfort of tourists.


That, in a nutshell is our experience about just how easy it was to travel to Cuba in late 2018.


A friend recommended to my son that we acquire WiFi cards because there are no cell service plans even just for calling for Americans. There’s no public internet to speak of either. The reason I’m sitting in the Plaza Hotel writing this is because they have, perhaps the only WiFI Card in Havana that works all across Cuba…as long as you’re in a Hotspot location operated by ETECSA. I’ll write much more about that in a later post too but for now, my WiFi time is up for now.

One additional thing I’d like to note is that our understanding of how these WiFi cards operate within their own networks is still puzzling to us. The fact that we used them successfully and had ample time to question people people about the various networks and how they operate, yet we still seem to lack good understanding of many of the basics is indicative of just how complicated so many simple things that we take for granted at home are in Cuba in late 2018. I’ve been told and suspect that it’s at least partially true, that the WiFi Cards we purchased at the hotel Plaza, which function everywhere within Cuba, aren’t really unique in that regard at all. And that any WiFi card purchased for that network will work anywhere within the country.

I still need to research that subject further to discover the truth and to be able to write knowledably and give proper advice for WiFi Cards.

More Information About Airlines & Visas

Scroll down in the Q&A’s to find this section.

A website I ran across while planning our trip has a great little blurb about Americans traveling to Cuba in 2018. You’ll find more information about which airlines fly to Cuba from the USA in the Questions & Answers section.

About vsajewel

Hi...I'm the author of 2 main blogs on WordPress...vsatips...where I write tech tips for mobile devices...primarily ios...2nd is vsatrends...where I write less about tech things and more about everything else. I also host a YouTube channel which I use to better illustrate some of the 'how to's' in my posts. I love everything about technology. Currently, my main interests/platforms are ios, Windows and Amazon Echo. Recently I decided we were spending way too much money with our local cable provider. So I decided to cut the cord. There is a definite learning curve, especially the antennae part, but we successfully did that and are now saving a boatload of money, so I write some about that. I also am extremely conscientious about security because of an event my family endured , so I write a lot about that too. Two sub-categories of security I tend to focus on are the password manager Dashlane and Hardware Firewalls. Last, I take a lot of notes and have been a beta tester for Evernote for many years. I love Evernote! In recent years Apple has beefed up Apple Notes a it’s become a fairly serious note long as its OK if you lose or mess up all your Apple note data. I write about those 2 note platforms primarily.
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